A beach with a row of wooden posts extending into the water, a sandy shore, and a clear sky.

Gasparilla Island Vacation Rentals

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Our top choices for Gasparilla Island vacation rentals

1. MALU LANI Inn & Marina

MALU LANI Inn & Marina
3.5 star property
Bokeelia
10.0 out of 10, Exceptional, (6 reviews)
"Overall, very friendly Gave me advice about the area Told me what live bands were playing that night Very fun definitely will be back"
United States
Kyle
The price is CA $246
CA $523 total
includes taxes & fees
Sep 16 - Sep 17
MALU LANI Inn & Marina

2. Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs
Englewood
10.0 out of 10, Exceptional, (54 reviews)
"It was a relaxing and beautiful stay!"
United States
Samantha I.
The price is CA $123
CA $415 total
includes taxes & fees
Sep 16 - Sep 17
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

3. Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
Englewood
10.0 out of 10, Exceptional, (64 reviews)
"The location was so convenient to the beaches. Very relaxing and a great place to go to truly feel like you are in a tropical oasis."
United States
Thomas
The price is CA $124
CA $416 total
includes taxes & fees
Sep 13 - Sep 14
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

4. The Suites at Fishermen’s Village

The Suites at Fishermen’s Village
3.0 star property
Punta Gorda Isles
9.8 out of 10, Exceptional, (1,319 reviews)
"Great place"
United States
Nidia
The price is CA $211
CA $237 total
includes taxes & fees
Sep 30 - Oct 1
The Suites at Fishermen’s Village

5. WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing
Oakland Hills
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is CA $122
CA $457 total
includes taxes & fees
Sep 13 - Sep 14
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

6. Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing
Oakland Hills
9.8 out of 10, Exceptional, (78 reviews)
"Nice stay in good location"
United States
John W.
The price is CA $123
CA $458 total
includes taxes & fees
Sep 13 - Sep 14
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

7. Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!
Englewood
10.0 out of 10, Exceptional, (50 reviews)
"The stay was, as usual, very nice! I can’t say enough about how wonderful the management team is here!! Outstanding!! See you next year!!"
United States
Chris N.
The price is CA $123
CA $415 total
includes taxes & fees
Sep 16 - Sep 17
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

8. Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Englewood
10.0 out of 10, Exceptional, (70 reviews)
"Excellent stay at Pura Vida——-clean, cool rooms, very relaxing experience on the property. It’s obvious Pura Vida put thought into the arrangement of outside amenities, including couches, dining tables, the spa, and numerous fruit trees planted around the property. Would 100% stay here again."
United States
Alex
The price is CA $124
CA $416 total
includes taxes & fees
Sep 25 - Sep 26
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

9. HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S

HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S
Oakland Hills
10.0 out of 10, Exceptional, (31 reviews)
"Beautiful home"
United States
Danail H.
The price is CA $106
CA $464 total
includes taxes & fees
Sep 14 - Sep 15
HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S

10. Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (18 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is CA $131
CA $469 total
includes taxes & fees
Sep 13 - Sep 14
Waterview Vacation Retreat Close To Ocean

11. WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches
Oakland Hills
10.0 out of 10, Exceptional, (29 reviews)
"Beautiful stay!"
United States
Terrica R.
The price is CA $122
CA $456 total
includes taxes & fees
Sep 13 - Sep 14
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

12. Casa Florida 🌴 waterfront home with boat ramp

Casa Florida 🌴 waterfront home with boat ramp
Bokeelia
9.4 out of 10, Exceptional, (11 reviews)
"This is our second time staying at this location and we will definitely be back! It is so convenient to have the boat ramp at the house and we love the boat lift. The house and property itself has everything you need and is always clean! "
United States
Morgan P.
The price is CA $154
CA $544 total
includes taxes & fees
Sep 15 - Sep 16
Casa Florida 🌴 waterfront home with boat ramp

13. Boat access only rental on private island

Boat access only rental on private island
Placida
10.0 out of 10, Exceptional, (13 reviews)
"We loved our stay, the house was as advertised! Great place to relax and enjoy the ocean!"
United States
Andrew S.
The price is CA $332
CA $762 total
includes taxes & fees
Sep 15 - Sep 16
Boat access only rental on private island

14. Matlacha Tiny Village

Matlacha Tiny Village
3.0 star property
Matlacha
9.0 out of 10, Wonderful, (297 reviews)
"So cute and clean nice dock to sit and relax or fish. Kayaks available to use free as well with life jackets paddles, etc. well equipped rental we can’t wait to go again! Great communication with hosts."
United States
Lori
The price is CA $183
CA $308 total
includes taxes & fees
Sep 15 - Sep 16
Matlacha Tiny Village

15. Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing
Oakland Hills
10.0 out of 10, Exceptional, (14 reviews)
"We had a wonderful month long stay. This home is nicely and tastefully decorated, clean and welcoming. Our host was very attentive to our needs and provided quick communication. Lots of extras for our trips to the beach. We would definitely stay here again!"
United States
Amber G.
The price is CA $133
CA $445 total
includes taxes & fees
Sep 20 - Sep 21
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

16. Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (5 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is CA $94
CA $323 total
includes taxes & fees
Sep 25 - Sep 26
Charming 2-bedroom house in Englewood with WiFi and AC

17. 3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing
Bokeelia
10.0 out of 10, Exceptional, (10 reviews)
"Property and house were beautiful, clean, quiet. Everything was top notch. Would definitely book again."
United States
Erik B.
The price is CA $182
CA $545 total
includes taxes & fees
Sep 24 - Sep 25
3BR Coastal retreat in peaceful Bokeelia with pool, bikes, ping pong and fishing

18. Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Oakland Hills
10.0 out of 10, Exceptional, (36 reviews)
"Everything we needed after a long day of fishing"
United States
WARREN R.
The price is CA $123
CA $458 total
includes taxes & fees
Sep 13 - Sep 14
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

19. Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
Bokeelia
9.8 out of 10, Exceptional, (18 reviews)
"peaceful and quiet in a great place to getaway"
United States
Louis
The price is CA $208
CA $349 total
includes taxes & fees
Sep 16 - Sep 17
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa

20. HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT

HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Rotonda Heights
9.6 out of 10, Exceptional, (14 reviews)
"Clean, comfortable, has everything you need for a vacation"
United States
Rick J.
The price is CA $139
CA $643 total
includes taxes & fees
Sep 13 - Sep 14
HEATED POOL-LANAI-BBQ-5 Mi to BEACH-BICYCLES-TENNIS-GOLF-BLISSFUL RETREAT
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gasparilla Island Hotel Reviews

Find out more about Gasparilla Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Gasparilla Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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