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

Gasparilla Island Holiday Rentals

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Our top choices for Gasparilla Island holiday rentals

1. 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 NZ$418
includes taxes & fees
1 Oct - 2 Oct
Charming 2-bedroom house in Englewood with WiFi and AC

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 NZ$527
includes taxes & fees
4 Oct - 5 Oct
Caribbean Tiki Hut relaxation. Enjoy the Islands & Boca Grande without the costs

3. 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 NZ$547
includes taxes & fees
17 Oct - 18 Oct
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

4. 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 NZ$527
includes taxes & fees
5 Oct - 6 Oct
Tiki Life ! Relax and Enjoy w/m discount! Close to beaches without the costs!!

5. 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 NZ$670
includes taxes & fees
12 Oct - 13 Oct
MALU LANI Inn & Marina

6. 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 NZ$522
includes taxes & fees
3 Oct - 4 Oct
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

7. 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 NZ$602
includes taxes & fees
18 Oct - 19 Oct
HEATED POOL, 85.00 PER NIGHT ! 2 LIVING ROOMS, 3 BEDROOMS-4 COMAST CABLE TV’S

8. 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 NZ$573
includes taxes & fees
1 Oct - 2 Oct
Water Front Boundary Vacation Home Villa close to beaches, golfing, Fishing

9. Waterview Vacation Retreat Close To Ocean

Waterview Vacation Retreat Close To Ocean
Oakland Hills
10.0 out of 10, Exceptional, (19 reviews)
"The property was great for 3 adults on a golf trip."
United States
Lisa D.
The price is NZ$584
includes taxes & fees
1 Oct - 2 Oct
Waterview Vacation Retreat Close To Ocean

10. 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 NZ$970
includes taxes & fees
4 Oct - 5 Oct
Boat access only rental on private island

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 NZ$571
includes taxes & fees
1 Oct - 2 Oct
WaterView 176B Sunny Vacation home 3 bdr, 2 ba Close to Gulf, Beaches

12. 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)
"Very nice stay at a beautiful new home!!"
United States
Nancy H.
The price is NZ$691
includes taxes & fees
4 Oct - 5 Oct
Family Villa King Bed Master suite 3 bed. + 2 baths + beach & fishing & golfing

13. 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 NZ$573
includes taxes & fees
1 Oct - 2 Oct
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

14. 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 NZ$575
includes taxes & fees
2 Oct - 3 Oct
WaterFront Boundary vacation! Close to beaches 3bdr2bath,golfing fishing

15. Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)

Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)
Manasota Key
10.0 out of 10, Exceptional, (2 reviews)
"This place has everything! Chris was friendly and helpful. I loved the location with a short walk to the beach and a view of the bay on the back porch. I will absolutely return"
United States
Christy S.
The price is NZ$516
includes taxes & fees
1 Oct - 2 Oct
Coastal Manasota Key Quadruplex, Dog-Friendly Studio, Snowbird Specials (Unit C)

16. 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 NZ$674
includes taxes & fees
5 Oct - 6 Oct
Casa Florida 🌴 waterfront home with boat ramp

17. Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests
Oakland Hills
9.8 out of 10, Exceptional, (28 reviews)
"Great alternative to a hotel. Beautiful and clean."
United States
Sadie A.
The price is NZ$728
includes taxes & fees
1 Oct - 2 Oct
Modern Retreat, 3Bedroom King bed + Master Bath near ocean, 6 guests

18. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (30 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
The price is NZ$1,090
includes taxes & fees
1 Oct - 2 Oct
Chadwick Cove Resort & Marina

19. CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL
Rotonda Lakes
9.8 out of 10, Exceptional, (32 reviews)
"We enjoyed our stay a lot, absolutely recommended property"
Canada
Dennis
The price is NZ$659
includes taxes & fees
2 Oct - 3 Oct
CHARMING FLORIDA GETAWAY 3BDR HOME WITH A POOL

20. 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 NZ$436
includes taxes & fees
13 Oct - 14 Oct
Charming 1-bedroom apartment in Bokeelia with WiFi, AC, pool & heated spa
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gasparilla Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gasparilla Island. 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 Gasparilla Island. 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 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 holiday 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 Gasparilla Island short-term rentals, that won’t be hard to do.

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