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Vacation rentals with a pool in Gasparilla Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Gasparilla Island

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guesthouse in Englewood

4.91 out of 5 average rating, 249 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Guesthouse in Cape Coral

4.94 out of 5 average rating, 117 reviews

Pool Modern Apartment

Location! Location! This apartment is close distance to Deli, restaurants and supermarket . The house faces the canal with breathtaking views we have cameras facing the canal and pool area in order to protect guests from any small animals that might be around. The apartment is attached to the main house with one bedroom one bathroom living room and a functional full kitchen in the Lanai area Is only for 2 persons. No children allowed. After May 2025 pool will be shared by 1 or 2 more guest.

Home in Captiva

4.97 out of 5 average rating, 114 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

Home in Captiva

4.92 out of 5 average rating, 106 reviews

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Home in Captiva

4.95 out of 5 average rating, 110 reviews

Steps To Private Beach Captiva Retreat Golfcart

Relax and Reconnect at Our Charming North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly (with applicable fees), it’s easily accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach start making memories

Villa in Englewood

4.93 out of 5 average rating, 107 reviews

Casa Blu: Serene Pool Villa, Minutes to Beach

Welcome to Casa Blu, your cozy retreat in Florida's sun-kissed paradise. Close to restaurants, parks, and beaches, and Old Englewood. Just 7 miles to Englewood Beach. The stresses of daily life melts away with its single-floor layout, comfy bedrooms with private baths await. Enjoy fast WiFi, Smart TVs, and a fully equipped kitchen. Unwind on the screened lanai or take a dip in the private saltwater pool. Everything's covered, from beach gear to a pack 'n play.

Home in Placida

4.96 out of 5 average rating, 112 reviews

My Little House with direct, quick access!

******2 King beds, 1 queen now. My Little house is fine, minus beautiful trees. I was unable to respond to inquiries during and after hurricane for almost a month. AirBnB penalized me for a poor response rate during that time. I've always had 100% evidently, I could've prevented the hurricane. It's 100% their fault, matter of fact, I made sure my guests were refunded before it hit. Questions? Feel free to ask. ***** I replaced the full size bed with a queen

Cottage in Bokeelia

4.99 out of 5 average rating, 120 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Also available: airbnb.com/h/aframeausable Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. There is a dock available here. Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources!

Home in Cape Coral

4.97 out of 5 average rating, 273 reviews

Dolphin beach house

* fantastic pool home located in the most desirable section of Cape Coral * Steps from the Yacht Club beach * Fishing and boating community * Home features a large paver patio for sunning and a screened Lanai with a private pool * This beach home has a grill outside for those who like to cook outdoors and a fully equipped kitchen inside * This home away from home has a Washer & Dryer * WiFi & Local TV * No Pets Please *

Home in Rotonda West

4.94 out of 5 average rating, 108 reviews

Waterfront Villa Shellflower with private pool

Villa Shellflower is located in Rotonda West on a large and quiet property. Right next to the property is the Rontonda River, a wide freshwater canal. The 1564-square-foot house has been furnished with great attention to detail. The large saltwater pool, the southwest-facing sun deck, as well as the cozy dining area provide the perfect holiday feeling. The next dream beach is only 20 minutes away by car.

Home in Englewood

4.86 out of 5 average rating, 102 reviews

Lemon Bay Luxury 6 BR Villa with Pool&Tennis Court

This beautiful house is located at the Lemon Bay and close to the Manasota Beach. The beach is just a 0.6 mile walk or 0.8 drive away. The property offers a 1/2 acre lot. This house offers, with a 34x12 feet swimming pool and own tennis court, a completely new rental experience. You will find the barbecue area outside of the pool area. The charging of EV is not allowed and an extra fee will be charged.

Island in Sarasota

4.97 out of 5 average rating, 317 reviews

New NOV Openings! Sarasota #1 Lux BEACH Villa

BOOK 2024 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

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Popular amenities for Gasparilla Island rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Punta Gorda

4.95 out of 5 average rating, 144 reviews

Seasonal vacation rental with Heated pool

Home in Englewood

5 out of 5 average rating, 26 reviews

Manasota Tree House - steps from the beach & bay

Home in Englewood

4.94 out of 5 average rating, 116 reviews

Island Home, Casita, Saltwater Heated Pool, Beach

Home in Manasota Key

5 out of 5 average rating, 19 reviews

The Sand Dollar-WALK to Beach in less than 1 MIN!

Home in Captiva

5 out of 5 average rating, 44 reviews

My Sea Shack~ 1 minute to beach, SH Club, G-Cart

Home in Englewood

5 out of 5 average rating, 16 reviews

Family Fun-Relaxing Home w/heated Pool & Game Room

Home in Placida

4.89 out of 5 average rating, 18 reviews

AMAZING Cape Haze Location -community kayak launch

Home in Englewood

5 out of 5 average rating, 39 reviews

Heated Pool*Outdoor Bed~BBQ~6Mi to Beach~2 Kings

Condo rentals with a pool

Condo in Englewood

4.95 out of 5 average rating, 107 reviews

Sunset Beach

Condo in Sanibel

4.88 out of 5 average rating, 234 reviews

Rare walkout condo on Sanibel beach-Fully Restored

Condo in Siesta Key

4.83 out of 5 average rating, 207 reviews

No Damage: Cozy 1BR Beach Condo on Siesta Key!

Condo in Englewood

4.78 out of 5 average rating, 111 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

Condo in Siesta Key

4.96 out of 5 average rating, 295 reviews

WE ARE OPEN—On the Beach; Siesta Key SunBum Studio

Condo in Sarasota

4.9 out of 5 average rating, 138 reviews

Gateway to Siesta Key - 1/2 mile to the Beach!

Condo in Sarasota

4.89 out of 5 average rating, 110 reviews

6 min. from Siesta Beach+heated pool+lake view

Condo in Englewood

4.94 out of 5 average rating, 136 reviews

Discounted Ground Floor Beach Studio on the Gulf!

Home rentals with a private pool

Home in Cape Coral

4.86 out of 5 average rating, 79 reviews

Luxury Waterfront Home with Pool

Villa in Cape Coral

New place to stay

New Listing! Casadesisa

Home in Cape Coral

5 out of 5 average rating, 6 reviews

Blue Oasis

Home in Cape Coral

5 out of 5 average rating, 25 reviews

Awesome Location W/boat Dock, Pool, & Kayaks!

Destinations to explore