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Pet Friendly Holiday Rentals in Longboat Key

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    Travellers to Longboat Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    16 Matching Rentals in Longboat KeyView all 98 rentals
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    Beachfront Condo on the Beautiful Gulf of Mexico1 / 37
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Charming Beach House in Longboat Key/ pool/pet/dock1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Village of Longboat Key, 1 BR & 1 BA Comfortable Cottage Very Clean1 / 15
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Longboat Key Retreat1 / 8
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2016
    Located on it's own in very quiet area we did not feel safe as no other people about. House was not as clean as it should have been lots of bugs etc. well equipped, not as near...
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    About this property
    Comfortable Turn-Key Tropical Home is just a two-minute walk to the private sandy white beaches and dazzling blue waters of North Longboat Key. There is ten miles of sidewalks for your enjoyment to bike, jog, or walk as well as direct access from your backyard to Durante Park, a gorgeous Nature...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Why stay with us? Sleeps 2 and small children. 1 bed, 1 Bath Cottages. One bedroom and 3 chairs. Dining table for 4 and outside patio for 4. We just update our cottage with New Queen bed, Linens, towels etc. We offer a full form mattress for children. Cottage available weekly or monthly in the...
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    Longboat Key, Florida 34228
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pet Friendly on Longboat Key1 / 25
    (27)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2018
    Really enjoyed our stay at Longboat. Great beach and great location. Really liked the condo, updated and clean, kids loved it. Will be back!
    Reviewed 21 July 2018
    The condo offered many extras including a blender and a food processor. Even though we did not use it, but it was nice to have for someone staying more than a week. We enjoyed...
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    About this property
    ****Please go to longboatbeachcom .**** for more information. I will email you a quote from my booking program. Condo was updated July 2016, so pictures are current. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit. Best...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, bright Bayside PET-FRIENDLY town home with partial Bay view and lush tropical landscaping. Unit has Full Kitchen, 2 LARGE BEDROOMS and 2 1/2 BATHS. Enjoy the fishing pier, large pool, tiki bar/restaurant. Come enjoy our Tropical Paradise! First level is extended parking garage. Second...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Paradise Cottage at Longboat Key1 / 28
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Cable/satellite TV
    • Grill
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 December 2016
    My husband and I, along with two other couples, just spent the most relaxing five days at Paradise Cottage. The name suits the house well. It was great. The house is very clean...
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    About this property
    Located between the nearby sandy white beaches and Sarasota Bay, enjoy plentiful water sports, fishing and relaxation. Paradise Cottage is a lovely vacation home located on Longboat Key between Sarasota and Anna Maria Island. The wonderful unit is just a 5min walk from the stunning white beaches...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find your tropical oasis in sought after LONGBOAT KEY. Wake to sunrises over your dock overlooking Sarasota Bay and catch the sunset sinking into the Gulf of Mexico-. Enjoy Serenity in this lovely home, or By Bike or Car Minutes to St. Armands' Circle or jump into your Boat; down the Deep Water...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded 2-bedroom private home with open floor plan including living room, dining area and well-equipped kitchen. Screened in lanai facing canal, gardens and active wildlife. One king bedded room and one queen bedded room with abundant closet space. Two newly renovated baths, washer/dryer,...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for tropical seclusion on a private island? Gorgeous sunsets with blue, blue waters? If so, then look no further. Nestled among the lush vegetation, your private Island Polynesian beach house awaits your arrival! Accessible only by boat,this getaway assures you complete privacy and...
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    Longboat Key, Florida 34228
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 20
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1400 sq ft free standing villa Our villa has 2 bedrooms, 2 bathrooms, living/ dining room, full kitchen and two bonus rooms. It is located on the bay which comes into the center of the community and features a marina - manatees and dolphins have been known to stop by! .Our unit is close to the...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Peaceful Cottage - Houses for Rent in Longboat Key, Florida, United States1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
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    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 January 2018
    Thank you for everything, we enjoyed your cottage. We plan to do this again next holiday. Perfect location, plenty of room for everyone. Nice to have beach chairs, and bikes...
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    About this property
    Fully equipped cottage reflecting its own unique style of a beach getaway in paradise, full of character, and quaint as can be! Very clean, and well maintained. This cottage is on a private lot with a separate entrance and parking. Laundry room with washer and dryer in garage. The residence has...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The home is a cottage located in historic Longbeach Village in the North end of Longboat Key, Florida. The home is near both the beach and the intercoastal waterway, with some water views. The beautiful Longboat Key beach is walking distance, about five blocks away. We purchased the home in 2011...
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    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    House Has 4 Bedrooms sleeps up to 8 people Fully stocked Kitchen with updated appliances across street from Beach and shopping and dining lots of water activities available Also has a bbq and a room in one bedroom that is private 2 tvs and cable are at house also in the summer time you can see...
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    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kick your shoes off, put on a pair of flip-flops, and walk down to the sparkling bay during your stay at this 2-bedroom, 2.5-bathroom vacation rental condo in Longboat Key! The condo is ideally located in the Cedars East community. Up to 8 guests can spend days at the beach, swimming in the...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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