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Holiday Rentals in Siesta Key, FL

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    Travellers to Siesta Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 23
    5 of 5 stars (39) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 27
    5 of 5 stars (16) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 19
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    About this property
    Siesta Key Vacation Condo all new, and an easy walk over to the #1 Beach in America. Complex has Pool, Covered Parking, Clubhouse, Marina. Two Bedrooms, Two full Bathrooms, Completely renovated Kitchen, all new Tile flooring throughout Condo, back Lanai catches glimpse of Sunsets, and front... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 4 weeks ago
    we stayed here in mid July 2016, Sue was very helpful on answering all my questions and I had a few .she's a very nice professional lady and that makes easier to communicate .the...
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    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    • Wi-Fi
    • Grill
    • Ocean Views
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    If you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably all in real beds. Just outside your door is Crescent Beach, consistently... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 25 May 2016
    The property is ideally located - i.e on the beach. The owner was extremely friendly and checked a couple of times to make sure that we had everything we needed. The condo has...
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    1 / 41
    4.5 of 5 stars (14) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
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    • Waterfront
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 6 August 2016
    Sandy Toes is a beautiful spacious townhouse on the gulf side. The owner thinks of everything that makes for a great trip to the beach. We could not have asked for more. We...
    5 of 5 stars Reviewed 21 June 2016
    We thoroughly enjoyed our stay in Siesta Key. The townhouse was well equipped and convenient to the beach. It was an extra plus having a garage and grill with table and chairs...
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    1 / 42
    5 of 5 stars (14) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    STAY IN YOUR OWN PRIVATE HOME ON SIESTA KEY - Fantastic Siesta Quarters Vacation Home!. Come make yourself at home in a nationally known artist's private residence on the exclusive north end of beautiful Siesta Key. Graciously appointed three bedroom, two bath with quality furnishings offered fully... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 5 weeks ago
    We had an amazing time on our vacation. The home is very clean, fully stocked with everything you could need or want, and Tiffany and her husband are the most gracious of hosts...
    5 of 5 stars Reviewed 27 July 2016
    Very clean and awesome place to stay on the island near everything.Rentor response super quick and one of the best places I have stayed on the island.
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    1 / 24
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Waterfront
    • Grill
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Casual Elegance can best describe this charming 1 Bedroom 1 Bath Villa on world famous Siesta Key Beach. This unit was re-modeled during the summer of 2014 by new owners and offers a crisp clean look and vibe for your vacation escape. The unit received numerous upgrades. Everything in the unit is... View all property information
    Location Information
    Siesta Key, Florida
    1 / 37
    5 of 5 stars (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your own... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 11 August 2016
    We had a wonderful stay st Sandy Toes last week. The apartment was clean, tidy and had everything you needed for a super beach holiday. Close to a couple of great restaurants...
    5 of 5 stars Reviewed 29 June 2016
    This place is as good as the previous reviews say it is. It has everything you need from pool floats to beach chairs to blow dryers to bicycles, dishwashing soap to laundry soap...
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    1 / 47
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. (all new photos coming later this month) Our ground-level oceanfront condo is the perfect place to unwind unplug and recharge the batteries. Fisherman's... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 3 weeks ago
    If you are an avid beach goer, you're average rental experience probably includes lifting and lugging a million beach accessories and toys (if you have kids) for what seems like a...
    5 of 5 stars Reviewed 16 August 2016
    This unit is literally 200 steps to the water. Fantastic ocean front appeal and it had literally the best master suite mattress that we've had in years for a vacation property...
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    1 / 17
    5 of 5 stars (7) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain shower, luxurious bedroom and... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 4 days ago
    Super updated unit in a great location super close to the powder sand beach. Community also has a nice pool - very quiet. Owner very responsive and helpful. Highly recommend.
    5 of 5 stars Reviewed 5 June 2016
    First, arranging this rental through trip advisor was really easy, owner was really responsive and kind. It was mine and husband's first trip to Florida, so really did not know...
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    1 / 23
    5 of 5 stars (33) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • Air Conditioning
    • Washer
    • Parking
    • Grill
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ebb Tide #3 is waiting for you: All quality furnishings & linens, fully equipped with everything you need for a fun and relaxing beach vacation! This cottage-style condo has been redone with your comfort in mind. Rated the #1 Beach in the USA: Crescent Beach on Siesta Key is literally a 3 minute... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 6 August 2016
    We recently stayed here. Sue was amazing, such hospitality. It was a quick walk to the beautiful beach and close to restaurants. We loved every minute of our stay. I can't thank...
    5 of 5 stars Reviewed 28 December 2015
    Loved everything about the place. sue was very hospitable and the place was spotless. Loved the proximity to the beach and the great restaurants within walking distance. Loved...
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    1 / 23
    5 of 5 stars (36) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This bright, cheerful and newly redone condo is located on Siesta Key which is renowned for its powdery white sand beaches and gorgeous sunsets. We have our own private, gated access to Crescent Beach and a lovely, large, heated pool. Both the pool and the beach are just a 3 minute walk from the... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 1 week ago
    My 3rd stay at Ebb Tide, 2nd in unit #2. i feel so at home here i wouldn't think of staying anywhere else.Everything is so convenient and the condo has everything you need and...
    5 of 5 stars Reviewed 5 November 2015
    Sue made us feel very welcome as she greeted us upon arrival . Our room was stocked with everything you need from the kitchen to beach supplies and everything in between what a...
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    1 / 16
    5 of 5 stars (8) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    • Patio
    • Outdoor Dining Area
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    GREAT Value !!! MVPROPERTIES AT SIESTA KEY Recently renovated and very conveniently located duplex villas at beautiful Crescent Beach on Siesta Key. We have (2) 2 bedroom 1 bath apartments. Each apartment sleeps up to 5 persons. Rent 1 apartment or both. The units are bright, updated, very clean... View all property information
    Location Information
    Siesta Key, Florida
    4 of 5 stars Reviewed 15 August 2015
    Ideally situated 2 minutes from the beach, restaurants,shops and 7 eleven. Very clean accommodation has everything that you need but does need a little refurb ie furniture...
    5 of 5 stars Reviewed 10 August 2015
    We had a great stay here. The owners were VERY pleasant. Everything that you would need for a beach vacation with a toddler was included and readily available. The place was...
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    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Housekeeping...
    • Balcony
    • Ocean Views
    • Patio
    • Terrace
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Great first impressions are evident from the moment you enter this lovely condo and enjoy the breathtaking ocean views from our private oversized lanai. We know you'll adore our comfortably decorated oceanfront condo and have the relaxing vacation you've been dreaming of. This unit unfolds as you... View all property information
    Location Information
    Siesta Key, Florida
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Waterfront
    • Satellite TV
    • Balcony
    • Washer
    • Parking
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Our 2nd floor, end unit condo was completely renovated over the winter of 2012– 2013. The floor plan was opened up to provide a nice airy feel and to enjoy the water view. All furniture, flooring and fixtures are new. The entry hall has a bench to store your flip-flops and other beach gear and... View all property information
    Location Information
    Siesta Key, Florida
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our condo has just been remodeled (October 2015) with granite counter tops, stainless steel appliances, dishwasher, cabinets, new tile, new bathroom, and new furniture. It is a second floor unit. We have included all the essentials for a family that likes to have the flexibility to make meals at... View all property information
    Location Information
    Siesta Key, Florida
    1 / 30
    5 of 5 stars (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Washer
    • Secure Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    “Pristine sand, blue skies - 'Number 1 Beach'” <BR><BR>The Best Thing to Come Home to after a Day on the Beach Is...<BR> ...a vacation home as comfortable as your own home. <BR><BR>Just a walk across the street to Siesta Key's world famous #1 Beach.<BR><BR> This split-level townhouse, has 2... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 31 December 2015
    I found this condo on trip advisor when I was researching places to stay in Siesta Key and we couldn't have been happier with our accommodations. My three kids and I spent our...
    5 of 5 stars Reviewed 14 September 2015
    The townhouse is nice, clean and spacious! My children enjoyed the beach, toys and pool each and every day. Michelle has the condo stocked with items that are needed for...
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    1 / 12
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Washer
    • Air Conditioning
    • Satellite TV
    • Porch
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Jamaica Royale condo #92 on the #1 beach in the USA, This 2 bedroom 2 bath garden view unit is located in the garden area of our beautifully landscaped property. This unit is on the first floor and reserved parking is right outside the front door. This unit has a full size washer and dryer for... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 29 December 2014
    Just returned from our first trip to Siesta Key. Had my wife and two adult sons with us. Unit was very clean and ready upon our arrival. Beds were extremely comfortable...
    5 of 5 stars Reviewed 10 May 2014
    My husband and I stayed here with our five children. This place was perfect for us. It was clean and comfortable. I was surprised to find every single thing I needed in the...
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    1 / 29
    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Balcony
    • Wi-Fi
    • Parking
    • Sauna
    • Grill
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Spacious Condo on Siesta Key is so centrally located you won't even need a car! 800 square feet, renovated, new, and super clean! King Bed in Bedroom and Sleeper sofa in living room provides 2 separate bed options with spacious closets ready for your things! Screened Lanai (porch). Central AC and... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 10 July 2016
    Very short walk to the beach! Sue is so friendly! The condo was in excellent condition! We will definitely stay here again!
    5 of 5 stars Reviewed 9 June 2016
    Sue B was very helpful leading up to my visit, going out of her way to make sure that I had everything I needed on arrival. The condo was exactly as described, very clean, very...
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    1 / 24
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Satellite TV
    • Balcony
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Split floor plan with each bedroom having a private full bath, tv and access to the lanai. Relaxing lanai with couch, two chairs and three end tables to enjoy a book or take a nap. Side Gulf View from side of lanai. 25 steps to the beach. Beach towels, umbrella and sand toys for the children... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 12 August 2016
    We loved our visit in Karen's "slice of paradise!" The property is right on the most beautiful beach with everything provided. And what the complex didn't provide Karen did - we...
    5 of 5 stars Reviewed 27 April 2016
    This condo was perfect for all our needs!! Karen, the owner, is a dream to work with. She got back to my messages immediately and was very attentive to any questions I had...
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    1 / 14
    5 of 5 stars (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 28 June 2016
    This place is as good as the previous reviews say it is. It has everything you need from pool floats to beach chairs to blow dryers to bicycles, dishwashing soap to laundry soap...
    5 of 5 stars Reviewed 27 May 2016
    My friend and I really loved this condo. It was very clean, spacious and beautifully decorated. The amenities were right on site such as washing machine and dryer. The closet...
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    1 / 22
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
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    • Ocean Views
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    LAST MINUTE DEALS NOW AVAILABLE AUGUST - JANUARY at our luxurious Villa#4 (on Crystal Sands, 6300 Midnight Pass Rd, Sarasota, Florida) - sleeps 6 and includes everything your family needs for your stay at the #1 beach in the USA. This Villa has easy access to the beach without leaving the property... View all property information
    Location Information
    Siesta Key, Florida
    4 of 5 stars Reviewed 3 weeks ago
    The two bedroom cottage is nice. Not luxury, but absolutely adequate. The beach is spectacular. The biggest drawback from the rental was the lack of any sort of outdoor...
    4 of 5 stars Reviewed 30 November 2015
    Villa was nice. It had all of the amenities needed for a comfortable stay. It was clean. It was only a short walk to the beach. It was close to town center.
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    1 / 27
    4 of 5 stars (10) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Patio
    • Waterfront
    • Satellite TV
    • Private Outdoor...
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    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome ! Sea Club II is Located steps away from the whitest sand and the # 1 beach in America, Siesta Key. Our location 200 yards away has an easement for private beach access. We are located on the intercoastal waterway of Little Sarasota Bay on the island of Siesta Key . Whether you are keen... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 4 weeks ago
    Thank you so much for the chance to stay in your condo. It was clean and had everything we needed for our 5 day stay. Siesta Key is a beautiful beach and we can't wait to...
    4 of 5 stars Reviewed 5 February 2016
    We arrived on January 9 and stayed 21 days. The property was lush with trees and hanging miss. After unpacking our car we went into the condo. And, we were greeted by a colorful...
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    1 / 25
    5 of 5 stars (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Patio
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Sauna
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. Fishing Pier. Leather, stone... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 6 January 2016
    THE best spot in the US to see the sunset over the Gulf of Mexico! A starting point for a long beach walk on Siesta Key's white sands as it is just steps to the beach. A short...
    5 of 5 stars Reviewed 7 April 2015
    This beautiful beach home had everything you needed to make your stay very enjoyable. Very clean,loved the beautiful view every morning.Enjoyed the shopping and the walks to the...
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    1 / 38
    5 of 5 stars (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Waterfront
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    WELCOME TO PARADISE! -- BEST LOCATION on SIESTA KEY! A very clean, cozy 3 level TH with a pool view, a few yards away from the beach, restaurants, bars, bank, grocery&drug store, 7-Eleven, free Wi-Fi, 140 channels on TV, fireplace, washer/dryer in unit, garage, grill, beach chairs, BIKES, beach... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 1 week ago
    My husband and I stayed here in August. Despite the hot and humid Florida weather (which, quite honestly, was the only negative part of the trip), we had a blast! We hosted some...
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please also visit siestakey-whitesands with the usual US ending. There you'll find lots of usedul information on the condo and a travel guide.White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek.Highlights of White... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 6 January 2016
    Close to all the excellent facilities of Siesta Key and within a comfortable walking distance of the magnificent Siesta beach, Grand White Sands 303 was the ideal place to 'chill...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is a large corner unit 1280 sq. ft in the center of private Crescent Beach which is deeded just for the Palm Bay Guests. This is a gulf to bay resort which gives you access to a pool , fishing pier & hot tub on the bay side along with restrooms. BBQ grills are on gulf & bay side and 1 outside... View all property information
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    Siesta Key, Florida
    1 / 25
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Relax, get away and enjoy Siesta Key's laid back lifestyle! Nestled in a quiet residential neighborhood, you'll love this large and comfortable 500 square foot studio apartment. It has a king bed and comfortably sleeps 2. The studio is attached to the owners' home, and features a king bed,... View all property information
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    Siesta Key, Florida
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Gorgeous 2 bedroom condo across the street from #1 voted beach Siesta Key. We have everything for your home away from home. The beauty of Sarasota will get your attention on your first visit. Siesta Beach is one of the top ranked beaches in the world! Its fine quartz white sand has a silky,... View all property information
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    Siesta Key, Florida
    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. The home is chic and hip in its mid-century modern beach cottage decor and style. The newly renovated kitchen is sleek in design and... View all property information
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    Siesta Key, Florida
    5 of 5 stars Reviewed 10 August 2016
    What a LOVELY place to stay!!! Sean was flexible, attentive and accommodating, and there was even fresh fruit, sparkling water and a personalized welcome sign waiting on the...
    5 of 5 stars Reviewed 30 July 2015
    I just wanted to say that if it wasn't for the comfort of this place my family would have had a real bad week. It rained everyday but 1 and that is unusual . With that being said...
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    1 / 14
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This wonderfully updated island vacation home has a spacious floor plan. There are tropical views from every window. The beautiful, heated private pool includes a spa and a waterfall. You can open the large patio doors to the screened in lanai that overlooks the pool and bring in the sound of... View all property information
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    Siesta Key, Florida
    5 of 5 stars Reviewed 22 July 2016
    We stayed for three weeks in this beautiful house. Great location between Siesta Key Beach and mainland. Also calm neighbourhood, clean house, fully equipped kitchen that had...
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    Harbor Towers Yacht and Racquet Club Unit 503 provides one of the best views in the building (fifth floor facing south/east). The glass enclosed Lanai with floor-to-ceiling sliding glass doors provides bright sunlight during the morning and afternoon with excellent views of the intercostal water... View all property information
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    Siesta Key, Florida
    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Delightful beach bungalow at Ebb Tide , only 2 minute walk to pool and powder white sand of Crescent beach, right across the street from restaurants,shops, bike and boat rentals, marina, 7 Eleven, and more. This darling tropical villa had everything you need for a great vacation. No one above you... View all property information
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    Siesta Key, Florida
    5 of 5 stars Reviewed 30 September 2014
    Was an excellent experience renting this villa. The beach is divine, it's a very friendly community, everything you need is close by. The villa owner was exceptional to...
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    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Lovely, fully updated 3 bedroom, 3 bath canal home 1 block from Siesta Village! Tropical private pool setting just off the main living area and the grand Master Bedroom. Second Master suite with private bath including soaking tub. All bathrooms completely redone in 2015. Quiet street literally... View all property information
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    Siesta Key, Florida
    5 of 5 stars Reviewed 24 June 2016
    On 5 day getaway to visit family in Florida stayed at this lovely, elegant, well decorated 3 Bdrm / 3 Bath home situated on quiet cul-de-sac street with canal in back. Pool-Lanai...
    5 of 5 stars Reviewed 23 June 2016
    We cannot express how much we loved this house in Siesta Key Florida. We have family in the area and are very familiar with vacation rental properties in the area and this was...
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    1 / 42
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you will often see fish jump and... View all property information
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    Siesta Key, Florida
    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Half Mile to the Beach This recently remodeled Beach house has both inside and outside living spaces. There is a combination Kitchen/dining/living area with windows on every wall allowing in loads of the wonderful Florida natural light. The kitchen is all white with stainless appliances and... View all property information
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    Siesta Key, Florida
    5 of 5 stars Reviewed 31 May 2016
    The space seems bigger than the pictures lead it on to be which is a plus! We really enjoyed our stay as the master bedroom was very spacious. We visit Siesta Key almost every...
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    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite show when you want to 50 inch... View all property information
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    Siesta Key, Florida
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Just across the street from sun kissed Siesta Beach, acclaimed as the Number One Beach in the United States. Noted for “The Whitest sand in the world”, set your sites for your next vacation at Our House At the Beach! Enjoy spectacular sunsets and Gulf views from 2 over-sized balconies in this... View all property information
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    Siesta Key, Florida
    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    I have tried to make this apartment as comfortable as your own home only at the beach. This unit has two bedrooms and two baths. It can accommodate six people with a king bed and two double beds. There are plenty of closet and dresser space, a fully-equipped kitchen, color TV's, VCR and/or DVD and... View all property information
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    Siesta Key, Florida
    5 of 5 stars Reviewed 8 August 2016
    This condo was very nice. Steps away from the gorgeous white sandy beach and convenient to shopping and restaurants. We were very impressed with not only the condition of the...
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    1 / 22
    6 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy... View all property information
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    Siesta Key, Florida
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Fabulous home on Siesta Key (Sarasota)( two weeks minimum stay ). Just 2 minutes drive to the beach & village. This home features 3 bedrooms and 2 baths with a large kitchen that opens to the family room. Great pool with southern exposure,and enclosed in a screen lanai for mosquito protection... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 15 June 2015
    As soon as we arrived we knew were going to have a happy stay at Palm's House! Our 5 person party was aged from 16 to 80 and we ALL had a wonderful time! The house itself is...
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    5 of 5 stars (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to... View all property information
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    Siesta Key, Florida
    5 of 5 stars Reviewed 26 June 2016
    This condo was perfect for relaxing beachfront in a beautiful, secluded location. The view was amazing, with the gorgeous gulf beach out back and the bay out front! And the...
    5 of 5 stars Reviewed 4 November 2015
    Unbelievable!!!! Beautiful views both in front and back of condo!! We watched the sunset every night from our window and sometimes went downstairs on the beach to watch it cause...
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    1 / 35
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Welcome to Casita Bayou! Casita Bayou is one half of the uniquely configured private home called the Coconut Bayou Cottage and it is the perfect escape for you and your family and friends. This property can be rented separately or combined to accommodate a large party! This side of the gorgeous... View all property information
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    Siesta Key, Florida
    1 / 42
    3 of 5 stars (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    YOUR PRIVATE GETAWAY ON THE KEY ASK ABOUT OUR SUMMER SPECIALS!!!!!!!!! Does not include Weekends or Holidays!!! Looking to relax, Flip Flop Cottages is the place to be for a quaint and private vacation in Siesta Key, Florida. Come and stay at our serene environment and enjoy and visit all the... View all property information
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    Siesta Key, Florida
    4 of 5 stars Reviewed 22 May 2015
    Nice overall for what we needed-good location for beach hoppers like ourselves. Could get to Lido beach and turn around and go to Venice beach with still many beaches between...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Spacious 1 bedroom, 1 bathroom, turn key furnished condo at Harbor Towers on Siesta Key. The unit has been totally remodeled, kitchen with granite counter tops, new cabinets, new lighting and stainless steel appliances. Bathroom has new shower and granite counter tops. Ceramic tile flooring... View all property information
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    Siesta Key, Florida
    1 / 36
    3.5 of 5 stars (4) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    What a great location! walk to Siesta Key village or relax on your private Gulf Beach or fishing on the pier at Sandy Cove. This 2 bedroom 2 bath unit is a 2nd level condo with pool views from the balcony. Enjoy breakfast after a short walk at one of the villages' quite restaurants before... View all property information
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    Siesta Key, Florida
    4 of 5 stars Reviewed 21 August 2014
    all people are going to take this one way or the other .we wasnt looking for a fancy place with wifi and all of that because u are on vacation . and its a time to enjoy . not stay...
    4 of 5 stars Reviewed 13 July 2014
    I had a wonderful experience at the condo. The only things I did not like was the limit on the time that children can be in the pool. The Children could only be in the pool from...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Jamaica Royale! We invite you to enjoy a visit to this lovely updated 2 bedroom/2 bath unit located in the beautifully landscaped garden area and only minutes away from the pristine #1 Siesta Key beach with private access from Jamaica Royale. Enjoy a swim in any of the 3 heated pools on... View all property information
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    Siesta Key, Florida
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Pelicans Perch! This is a gorgeous condominium complex that boasts spectacular amenities as well as a heated pool, only a few minutes walk to the beach access. This property has undergone extensive renovation, which was completed in January. Our winter guests will enjoy the luxury of all... View all property information
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    Siesta Key, Florida
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Home Enjoy the luxury and amenities of Siesta Key from the comfort of your own private villa. Exquisitely decorated, encompassing the ambiance and excitement of Siesta Key, the Great Blue Heron provides you with all the luxuries and comforts you will need for the perfect beach getaway.... View all property information
    Location Information
    Siesta Key, Florida
    Siesta Key Vacation Rentals

    Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key vacation rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theater, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.

    Lions, Tigers & Circuses

    When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.

    Gardens & Aquariums

    Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.

    Locomotives & Science

    Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theater, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.

    History & Baseball

    From your money-saving Siesta Bay vacation rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.