Vacation rentals with a kayak in Little Gasparilla Island

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Top-rated kayak rentals in Little Gasparilla Island

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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

ﺩ.ﺇ1,060 per night

Guest favorite

Cottage in Englewood

4.9 out of 5 average rating, 110 reviews

Free bikes/kayaks/walk to beach/2bed/2bath #2

Unit # 2 Beautiful 2 bed 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. This cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

Nov 11 – 18

ﺩ.ﺇ554 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 25 – Nov 1

ﺩ.ﺇ851 per night

Guest favorite

Villa in Port Charlotte

5.0 out of 5 average rating, 8 reviews

"Everglade Kiss" 3b 2b BBQ, hot tub

"Everglade Kiss"3 bed 2 bath 1 car garage villa, quartz kitchen corner tops ,65 inch TV in living room, lanai has 16 jets hot tub . Back yard is shareable.South West Florida's prime boating and beaching communities with the Charlotte Harbor and The Gulf of Mexico minutes away.Community offers public sidewalks, parks, with boat ramp, picnic area, playground. The waterways provide place for kayaking, paddle boarding, and fishing. Enjoy a memorable visit when you stay in this unique place.

Aug 31 – Sep 7

ﺩ.ﺇ431 per night

Guest favorite

Guest suite in Englewood

4.98 out of 5 average rating, 180 reviews

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The rental includes use of bikes and kayaks. Kayaks are kept at 998 Oxford Dr. We are available to launch or to help you launch kayaks at a local spot. Front porch pictured is part of the main house and is use of this space is not included.

Oct 15 – 22

ﺩ.ﺇ523 per night

Guest favorite

Home in Venice

4.89 out of 5 average rating, 161 reviews

Venice Pool Villa with Bikes Kayaks Great Beaches!

Relaxing pool home with 2 bedrooms, 1 king bed, 1 queen bed, 1 sofa double bed and one single foldout bed. 2 bathroom pool home just a 8 minute ride away from Manasota beach. Venice beach and caspersons beaches close by too. A great selection of restaurants and plenty of shopping and convenient grocery stores just 5 minutes away!. Also close to bike trails with two FREE bikes at the house and FREE kayaks too. My home is great for everyone! Pets welcome with pet fee, large fenced yard!

Sep 21 – 28

ﺩ.ﺇ537 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!

Oct 24 – 31

ﺩ.ﺇ332 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.

Jun 18 – 25

ﺩ.ﺇ1,063 per night

Guest favorite

Home in Matlacha

5.0 out of 5 average rating, 142 reviews

The Secret Island Retreat HeatedPool/4b/open water

Free Heated Pool with open Panoramic Bay Views with Amazing Sunsets from this open layout with 4 bedrooms , a den, 3 bath, 2 car garage. 3200 sq ft. 2nd floor has an oversize owners suite with picture windows over the bay and provides an abundance of space for sitting area or quiet space. Three guests rooms + den. Don't forget to relax & enjoy the breeze on the 2nd story balcony...the perfect retreat. Kayaks, 2 boat lifts, fishing poles, bicycles, games, Grill and much more.

Jul 23 – 30

ﺩ.ﺇ1,738 per night

Guest favorite

Cottage in Placida

4.97 out of 5 average rating, 37 reviews

Simply Adrift Island Cottage

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off FL's West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

Oct 11 – 18

ﺩ.ﺇ1,179 per night

Guest favorite

Villa in Englewood

4.92 out of 5 average rating, 110 reviews

Magnificent Waterfront! Kayaks-Pool-Beach! gs

Fantastic Manasota Key Location! Upstairs at Blue Island Inn, waterfront “Seaglass Villa” dazzles with spectacular Bay views! 2 cozy bedrooms; 1 bathroom, kitchen & cozy family room. On-site resort pool overlooks stunning Lemon Bay. 5-minute walk to ocean-side beach or enjoy “Bay-front beach” out back. Quiet island street. low-key quiet respectful vacationers. 1 car parking spot. No visitor parking. No boats. No pets. No smoking. Free use of kayaks!

Oct 20 – 27

ﺩ.ﺇ567 per night

Guest favorite

Home in Placida

5.0 out of 5 average rating, 7 reviews

Just listed! BRAND NEW Coastal Sol on Palm Island!

Escape to the Coastal Sol retreat and be one of the first guests to enjoy this newly built home! This brand new 3 bedroom, 2.5 bathroom sanctuary is located on the exclusive Don Pedro-Knight-Palm Island, accessible only by private boat or a 5 minute car ferry ride. Coastal Sol offers a perfect blend of seclusion and accessibility. Enjoy 'old Florida' island life pursuits, complete with spectacular sunsets and leisurely strolls on uncrowded beaches.

Aug 19 – 26

ﺩ.ﺇ1,434 per night