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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.
    All 96 Rentals in Longboat Key
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    LastMinute Discounts-Condo in  Beach Resort 2/2 -Heated Pool,Tennis&Shuffleboard1 / 21
    (14)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Discount of 30% for our last availability in July: 15-18, 2018 Beautiful 3rd floor 2BR/2BR unit #309, overlooking pool, in Sand Cay Beach Resort on the exclusive island of Longboat Key. South facing balcony with sunshade and umbrella. Striking views to the beach from the balcony but you only pay...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Away to Paradise! Unit 301 with 180 degrees unobstructed Mexican Gulf View. Beachfront condos on Florida's gulf coast. This is a corner condo so you have a more space and side window view. A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Light and bright condo directly on the beach, totally renovated in 2014. Walk right out from the screened lanai to sink your toes into the warm sand. Modern kitchen with breakfast bar, open living/dining floor plan with quiet bedrooms set apart from family activity. Additional amenities: Beach...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Connect to the beach from this quiet all-on-one-level end unit or take a few steps to the pool from the shady lanai. Simply appointed with everything you'll need to make your beach vacation a happy one from beginning to end. Quaint & serene. You even have a partial view of the dunes and the Gulf!...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 12 is a two bedroom condo available for rent 4-13 thru 4-20 2019 (Saturday to...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Cool and serenely decorated to reflect a tropical hideaway. Stainless steel kitchen, with plenty of cupboards and spacious granite breakfast bar. Designer bedding in the carpeted king master and queen guest bedrooms which are separated from the family activity areas. Walk directly out to the beach...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Terrace
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    SUMMER- FURNISHED- 2 bedroom/ 1.5 bathroom unit is ready to go! Completely turn key, with bicycles,kayak and beach chairs! Amazing pool right on the Sarasota Bay! Great Kayaking right on the property! Private beach access on the Gulf of Mexico drive. The house has been totally remodeled with...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    A light and airy end unit, with decorator touches throughout. All the comforts of home plus walk right out to the beach or enjoy sunset views from your screened lanai. Wheel chair accessible with walk-in shower, Connect to the beach, and leave your worries behind. Quiet bedrooms set apart from...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    LONGBOAT KEY - Beautiful Gulf to Bay. Bayport Beach and Tennis Club is a rare find. This award winning, amenity-rich community at sea’s edge is situated in the middle of Longboat Key. A popular residential enclave of 136 homes on 27 acres of picturesque gardens. Bayport is bordered by the Gulf of...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beachfront townhouse just steps from the shores of the Gulf of Mexico via your ' stairway to the sand' from the second floor screened lanai adjacent to the spacious, open living/dining area. Enjoy sunsets and sea breezes in this comfortably furnished 3 bedroom and 2 bathroom condo with sweeping...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This upscale townhouse with luxury conveniences features a streamlined and upgraded granite and tile kitchen and bathroom on the first level. A spacious, open dining and living area leads to the screened lanai facing the Gulf with stairway to the beach. All bedrooms are carpeted. Second level...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Zilli Tower 503 is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the Zilli Collection . Each with the Zilli touch of amazing view, decor, ( not typical wicker furniture , silly beach artifacts 40 year old flooring etc 1 SIZE fit all .) We...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
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    • Outdoor Dining Area
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    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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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    This newly built waterfront home will take you to another place and time. Tucked away in native tropical vegetation perched on the Bays edge looking out to Longboat Pass, this home is the perfect retreat for a couple or small group. Modern, open floorpan with a Scandinavian feel boasts hardwood...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
    • DVD Player
    • Sauna
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    • Hot Tub
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    About this property
    Enjoy your family vacation in the two beds,two baths 1,503 sf spacious condo,fully turn key equipped waiting for you to move-in. All utilities are free including hi speed internet, Wi-Fi, three flat TV's, landline phone, in-unit washer and dryer. Condo unit 203 located on the 2nd floor,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
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    About this property
    Wonderful and clean second floor condo that is just steps away from the gulf of mexico and its wonderful beach. Pool and workout facilities right next to condo. Condo has a master suite with a king size bed and a second bedroom with a queen size bed. We are priced right and ready to negotiate to...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a spacious house, located in Halyard Lane on Longboat Key, close to St. Armands Circle (3 miles) and private beach (0.5 miles). With 3 bedrooms, 2 bathrooms, equipped kitchen and TV equipped living room, it can perfectly accommodate a family or group of friends of 6 guests. The house is...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 10 is a one bedroom condo available for rent during week 14 April 6 - 13...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Comfortably appointed to reflect the sand and sea view from spacious living/dining area on first level of light and bright townhouse. Laid back, island-style décor with screened lanai beachside. 2nd floor master bedroom features a balcony perfect for sunset watching or star gazing. Additional...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beach & Tennis Enthusists Vacation Condo1 / 22
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    About this property
    We have beautiful condos at Club Longboat. One is a beachfront condo and the other is a garden unit with a restricted view of the Gulf of Mexico from the living room balcony. They are fully furnished, three bedroom units (one king bed, two twin beds, one queen bed or sofa sofa bed), full size...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    About this property
    Beautiful two story condo with views of the Gulf of Mexico. This condo includes a dining room, full kitchen, deck overlooking the Gulf of Mexico, housekeeping, free breakfast every Monday morning. The feeling of a private beach home with the benefits of a condo, including full access to a pool, hot...
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    Longboat Key, Florida 34228
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    On the Beach - Brilliant Sunsets - Balmy Breezes Quiet & secluded - Only three other units in the building. The surf, dolphins, incredible sunsets all from screened balcony! Enjoy warm sunny days and tropical nights while staying in a secluded romantic setting in our two-bedroom villa on your...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Beautiful ground floor beachfront (on Gulf of Mexico) 3 bedroom, 2 full bath condo on Longboat Key. NOTE THIS UNIT IS ONLY AVAILABLE BETWEEN jUNE 1 AND SEPTEMBER 20 OF EACH YEAR. CHECK OUR CALENDAR FOR AVAILABILITY ON SPECIFIC DATES IN THAT RANGE. Fully furnished kitchen, washer and dryer (in...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    About this property
    Wonderful Beach front condo in magnificent Longboat key. You will Love the the beautiful private Balcony with sensational beachfront views of turquoise Gulf waters. This unit is on the second floor with an elevator for easy access. The space is a roomy 1175 sqft with a full size kitchen living room...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Center courtyard unit just steps from the pool, with palm trees and Gulf views from the screened lanai directly off the open living and dining area. Wicker furniture and plump floral cushions make a delightful and comfortable décor. Bedrooms are located away from the family activity areas in this...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This spacious, bright and airy end-unit townhouse begins on the second level with a private beach entrance, and offers a sundeck on the third level with a spectacular view of the Gulf. The comfortable beach-house décor makes it a great place to kick back and relax while enjoying Gulf views from...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 11 is a one bedroom condo available for rent during 3-23 thru 3-30 and 4-13...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Beautifully renovated unit with tile floors and granite counter tops. Unit has full washer and dryer. Lanai is enclosed with glass sliders for extra functionality. First floor unit has beautiful bay views and is accessible by stairs or elevator. The master bedroom overlooks the bay and the second...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Little Gull Cottages is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 13 is a two bedroom condo available for rent during week 12 (Saturday...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment. • Very private and quiet first floor, 1600 ft. unit with lush garden views. • Master suite with office niche, king size bed, walk-in closet and double sinks in bathroom. • Guest bedroom with...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    You'll discover the perfect recipe for enjoying a beach vacation in this townhouse with its totally renovated and updated granite and tile kitchen and picture perfect décor. Soft shades of aquamarine provide a quiet color scheme for relaxing while enjoying the spectacular views of the beach and...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Newly remodeled and updated, this bright and elegant second floor beach escape has a private entrance to the pool. Serene and secluded, palm trees shade your master bedroom window. No formal balcony, but a wall of sliders in the expanded living room open wide to the partial Gulf view and gentle...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    This apartment is ideal for a vacation rental or bed and breakfast as it is literally 100 yards from the Ocean with panoramic views of the Caribbean from the lounge and bedrooms. Recently completely renovated with polished granite floors and upgrades to the kitchen, bathroom and bedrooms, the...
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    Longboat Key, Florida 18470044
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Holiday paradise on the stunning Florida west coast on the island of Longboat Key. Stunning, elegant and luxurious complex. For selfcatering there is the kitchen with all necessities and modern devices. Of course, there is a washing machine and dryer avialable. First-class furnishing. Safe and...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright and cheerful with beach-style decor and pops of color. Tiled throughout, off the open living/dining area you'll discover a secluded lanai under the palm trees just steps from the pool. Relaxation starts here, where everything is all on one level and it's an easy-breezy walk to the beach.
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Ocean Views
    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two Month Minimum Rental Required by Condo Association. This gulf-front Longboat Harbour Towers, sixth floor condo(4401 Gulf of Mexico Drive)has panoramic views of the Gulf of Mexico with NEW KITCHEN, BATHROOMS, AND WINDOWS. The sunny, cheerful interior encourages relaxation from the time you...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Internet Access
    • DVD Player
    • Ocean Views
    • Air Conditioning
    • Housekeeping Included
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this beautiful Gulf-front sunny unit with vaulted ceilings and spectacular views. The open floor plan of living room, dining room, kitchen and den offer full views of the sparkling turquoise water, blue sky and white sandy beach. Freshly redecorated in natural tones of soft blues, greens...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright and cheerful with beach-style decor and pops of color. Tiled throughout, off the open living/dining area you'll discover a secluded lanai under the palm trees just steps from the pool. Relaxation starts here, where everything is all on one level and it's an easy-breezy walk to the beach....
    View all property information
    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Balcony
    • Patio
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Carefree décor brings the beach right inside with the soft blues and yellows of sea and sun. This townhouse has spacious living/dining area with fully equipped corridor kitchen on first level, and two carpeted bedrooms on second level including a private balcony off the master bedroom. Additional...
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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This tennis resort boasts gorgeous views of Mangrove wetland and is just a short walk from stunning gulf beaches! The community pool makes this a lovely family-friendly getaway. Find great bird-watching and wildlife viewing from the balcony, or stroll through Mangrove tunnels on the boardwalk....
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    Location Information
    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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
    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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    Location Information
    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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