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Holiday Rentals with Pools in Sanibel

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    22 Matching Rentals in SanibelView all 50 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This nautical themed waterfront condo is the perfect combination of at-home comfort and vacation getaway. Enjoy nightly sunsets from your furnished, screened in balcony overlooking Sanibel and Florida's barrier islands, and relax within a bright and open concept floor plan with tray ceilings, crown...
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    Sanibel, Sanibel Island 33908
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    '' Vitamin Sea '' Beachfront condo is right on the beach , on the Gulf of Mexico , you just can't get away from the beach . Copy and paste this 3D Virtual Tour link to your search engine and transport yourself to my tropical paradise This beautiful 1300 SQ.FT. 3rd floor CORNER UNIT 2...
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    Sanibel, Sanibel Island 33957
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Being the closest condo to the Gulf of Mexico, you are never going to want to leave Villa Sanibel 1E!! Wake up to the sound of waves crashing ashore and enjoy your morning coffee while you look out at the ocean on your private porch. You can’t get any closer! This newly furnished, beautiful, unit...
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    Sanibel, Sanibel Island 33957
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming cottage is truly an islanders dream come true featuring a desirable west end location with 3 bedrooms and 3 bathrooms and stunning views to match! The beautiful home has been recently updated throughout and boasts a renovated kitchen, dark hardwood floors, outdoor wrap around deck...
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    Sanibel, Sanibel Island 33957
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Calypso Tides So much to offer, heated pool and spa, PET (dog) Friendly, Sleeps 10, Walk to the beach, Golf within minutes, bikes included and Sleeps 10...All on Sanibel Island. Newly Constructed in 2016. Amazing Key West appeal and gorgeous Sanibel river views in this recently built stilt...
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    Sanibel, Sanibel Island 33957
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandpebble 2E is a beautiful and spacious 2 bedroom, 2 bath condo located right on the Sanibel River! This updated condo features an open floor plan, river front views, and a short stroll to the beach just across the street. Enjoy a relaxing dip in the heated community pool or play a few rounds of...
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    Sanibel, Sanibel Island 33957
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Smoking allowed
    About this property
    Come on in and make yourself comfortable in this Punta Rassa Condominium overlooking the water and Sanibel Causeway. The water view of the shimmering gulf from this rental condo is nothing short of breathtaking! The enclosed lanai offers the flexibility of opening the glass doors to enjoy the gulf...
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    Sanibel, Sanibel Island 33908
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This very near beach luxury home has everything you need for the perfect vacation. Four bedrooms three bathrooms, a large heated screened pool, hot tub with the lake views. Located in Beach view Estates and Sanibel Island Golf Club. Walk into the large living room with built in shelves,...
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    Sanibel, Sanibel Island 33957
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Please be aware that the Annual Pointe Santo Pool Closure dates for 2018 will be Tuesday, September 25th & Wednesday, September 26th *** ESCAPE TO SANIBEL! Pointe Santo C42 is a stunning top floor, penthouse condo that boasts 2 bedrooms, 2 bathrooms, a screened lanai and a private rooftop deck...
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    Sanibel, Sanibel Island 33957
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW RENTAL PROPERTY JUST RECENTLY ADDED TO OUR INVENTORY WITH OPEN AVAILABILITY -- GREAT FOR A LONG TERM RENTAL! Condo amenities include: 2 bedrooms/2 bathrooms -- 1 King bed, 2 Twin bed & a Queen sleeper sofa (sleeps 6), free WIFI & cable, fully equipped kitchen, 2 heated shared pools, 2...
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    Sanibel, Sanibel Island 33957
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Air Conditioning
    • Washer
    • Secure Parking
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely remodeled with beautiful finishes! This two bedroom two bathroom Bay Front Mariner Point condo has stunning views and a stunning interior. Walk into the remodeled kitchen with glass tile backsplash, white quartz countertops, and stainless appliances. A breakfast bar with seating for...
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    Sanibel, Sanibel Island 33957
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Please be aware that the Annual Pointe Santo Pool Closure dates for 2018 will be Tuesday, September 25th & Wednesday, September 26th *** Welcome to paradise at Pointe Santo B22! This 2 bedroom, 2 bath condo plus den offers all the luxuries of home and more! Pointe Santo de Sanibel features...
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    Sanibel, Sanibel Island 33957
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome home to your new island oasis featuring 3 bedroom & 3 bathrooms and a large enclosed outdoor patio equipped with your private pool and hot tub! 'Beachside Bliss' is luxury living at it's finest! The home itself is located on a beautiful block in the Beachview Estates neighborhood and...
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    Sanibel, Sanibel Island 33957
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Parking
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tanglewood 1A is a beautiful & inviting 3 bedroom, 2 bath condo with expansive views directly to the Gulf of Mexico. Conveniently located on the east end of the island on a quiet dead end street, this condo has all you could ever want or need in your next Sanibel rental! The kitchen, living/dining...
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    Location Information
    Sanibel, Sanibel Island 33957
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BRAND NEW PROPERTY TO OUR RENTAL PROGRAM. OPEN AVAILABILITY FOR MULTIPLE MONTHS AVAILABLE. NEW IMPROVEMENTS TO THE HOME WILL INCLUDE NEW FLOORING, ALL NEW FURNITURE THROUGHOUT, AND BATHROOM UPDATES. (New pictures to come following completion) 'Sunset Hideaway' is a charming 2 bedroom, 2 bathroom...
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    Sanibel, Sanibel Island 33957
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the “Ding Darling Wildlife Sanctuary,” this charming one-level Sanibel home is just minutes away from Bowman’s Beach, one of the best beaches on the Island. The “Wild Lime” house was completely remodeled and professionally decorated in 2017 and is now being offered for rental for the...
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    Sanibel, Sanibel Island 33957
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fresh, Bright, Clean and Relaxing! Mariner Point 732 is the perfect place to enjoy everything Sanibel Island has to offer. The open living room features a flat screen TV, two comfy couches, sliding glass doors that open to the lanai and beautiful views of the tropical surroundings. Relax on the...
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    Sanibel, Sanibel Island 33957
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk into the open, colorful living room with vaulted ceilings, comfortable couch, flat screen television and tropical views. The spacious kitchen is everything a gourmet cook would want. Granite countertops, a large granite island, stainless appliances and spacious white cabinets. The tropical...
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    Sanibel, Sanibel Island 33957
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct Water Access to the Gulf of Mexico! This three bedroom spacious home is a boaters dream. A large dock, two working davits and deep water access. Spend the day salt water fishing, watching manatees, dolphins and sea birds all from the comfort of your private dock. As you walk into the...
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    Sanibel, Sanibel Island 33957
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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