Vacation rentals with a pool in Little Gasparilla Island

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Little Gasparilla Island

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Condo in Placida

4.96 out of 5 average rating, 52 reviews

Beachfront Island Condo w/ Pool &Ferry Service Inc

Come Enjoy our Newly Updated Island Condo with Magnificent Gulf Views. 2 private SW facing decks offer a.m Sun, Gulf, Palm & Pool Views. Beautifully furnished with everything to enjoy your vacation. Boat friendly dock, gated mainland car parking, ride FREE ferry 10 min to the island, miles of beach to roam, shell, hunt for shark teeth or fish. Walk over the boardwalk looking left & right–seeing only shore birds & dolphin or venture out for the most Prime Fishing & Kayaking Florida has to offer

Apr 23 – 30

G$60,350 GYD per night

Superhost

Guesthouse in Englewood

4.93 out of 5 average rating, 234 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.

Sep 15 – 22

G$69,360 GYD per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

NEW 4 Day MAY opening Sarasota #1 Luxury Villa

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, 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!

Dec 26 – Jan 2

G$133,919 GYD per night

Guest favorite

Guesthouse in Englewood

4.97 out of 5 average rating, 202 reviews

Shabby chic cottage with pool one mile from beach

This adorable shabby chic decor style studio cottage for 2 is located on one acre of old Florida landscaping. Great area for walking, biking, for exercise. Included with this home is access to a pool and large, lovely lanai, just outside the door. Head south for 7 min to historic Dearborn St or north for 3 miles to Venice. This location offers peace and tranquility combined with accessibility to endless activities nearby. 2 twins OR one King, per your preference. The pool is unheated.

May 18 – 23

G$24,047 GYD per night

Guest favorite

Home in Captiva

4.97 out of 5 average rating, 107 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

Feb 15 – 22

G$139,573 GYD per night

Guest favorite

Home in Englewood

5.0 out of 5 average rating, 19 reviews

Cape Haze Cottage

New 2023 Cape Haze Cottage , 3 bedroom 2 bath elevated canal front pool home. Quiet waterfront neighborhood with easy access to everything this amazing area has to offer. Screened lanai provides sunset views, private pool, outside shower, steps away from canal front for Kayaking and fishing or just watching the endless variety of nature. Situated just six minutes from stump pass by boat, access to the gulf , beaches and fishing both inshore and offshore. This is a piece of heaven.

Oct 8 – 15

G$48,465 GYD per night

Guest favorite

Guest suite in Matlacha Isles-Matlacha Shores

4.84 out of 5 average rating, 316 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

Dec 5 – 12

G$18,890 GYD per night

Guest favorite

Home in Placida

4.85 out of 5 average rating, 13 reviews

AMAZING Cape Haze Location -community kayak launch

Ready for warm sunshine, tropical breezes and lush landscaping? Spaniard's Retreat is the ideal location for your get away. This home is set in the charming Old Florida neighborhood of Cape Haze. Old banyan and pin-oak trees line the picturesque streets where homes are spaciously placed. Upon entering you will be greeted by the panoramic sliding doors overlooking the heated pool and spa. This truly feels like a private oasis. 3 bedrooms and 2.5 baths offer generous accommodations.

Sep 27 – Oct 4

G$60,519 GYD per night

Guest favorite

Cottage in Englewood

4.9 out of 5 average rating, 150 reviews

Free Kayaks! Waterfall Pool! Beach! am

In a prime Manasota Key location, our talented interior designer created this beach bungalow gem with 2 bedrooms and sofa sleeper, Smart Tv's & granite kitchen with dining set. Walk only 1 minute until your toes are in Gulf of Mexico at delightfully uncrowded beach! 5 walk to Stump Pass. Longer walk or free shuttle to good restaurants with live music. Unwind in on-site Swim Spa with waterfall & massage therapy jets in common area. Spot dolphins with free Kayaks. Peaceful, quiet

Nov 17 – 24

G$35,437 GYD per night

Guest favorite

Condo in Englewood

4.93 out of 5 average rating, 114 reviews

Immaculate Ground Floor Beach Studio on the Gulf

Please note: This complex had minimal damage, but you may see remnants of the hurricane in the complex. There is a protective tarp on the roof of my building even though there was very few tiles that blew off in the storm. There is a separate, beachside building with the same protective tarp & is getting new stucco on the west side facing the beach. You do not see the face of this building from my property as my place faces the pool. *See my pictures for more details*

May 15 – 20

G$39,465 GYD per night

Guest favorite

Home in Placida

5.0 out of 5 average rating, 24 reviews

Close to beaches, canal view, golf, fishing

Cape Haze Hideaway! Salt Water Canal, pool, clean, serene!! Situated nicely near beaches, golf, bike paths, lovely kayaking, boating, restaurants. Come enjoy our home and live like a local. Work from home with fast WIFI!! Walking distance to a nearby shopping center. Amenities pictured in the photos section are available at no extra charge, ask for availability. Pool has the option to be heated, but requires an additional charge per day. Our house is your house!

Nov 8 – 15

G$37,418 GYD per night

Guest favorite

Home in Englewood

4.99 out of 5 average rating, 102 reviews

Paradise on the Bay

Waterfront pool home with all the amenities. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fish from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 2 Kayaks and 1 pebble boat is available for your enjoyment.

Feb 25 – Mar 4

G$87,985 GYD per night