
Little Gasparilla Island Vacations from $670
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The Latest Little Gasparilla Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Matanzas Inn Bayside Resort and Marina
Price was $1,548, price is now $670 per person
$670
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,013 reviews)
Door slamming under cottage in the morning can be an early wake up call lol
Reviewed on Nov 14, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $1,472, price is now $762 per person
$762
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
18.4/10 Exceptional! (701 reviews)
The property was beautiful. The staff was friendly. The bed and pillows were amazing.
Reviewed on Nov 15, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Price was $3,998, price is now $2,087 per person
$2,087
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
19.2/10 Exceptional! (294 reviews)
Really loved our stay! We had a 3 bedroom apartment with plenty of space and modern amenities. 3 gorgeous walk in showers, enormous bathtub. The complimentary breakfast was very useful with small children. Pool and beach access were great. Complimentary paddle boards and kayaks made it really fun. Location is nice as there is a Breeze shuttle stop at the end of the road but the property itself is in a very quiet location. The sunset was fabulous. We will be back!
Reviewed on Oct 25, 2025

Compass Hotel by Margaritaville Anna Maria Sound
Save 100% on your flight
Price was $1,348, price is now $724 per person
$724
per person
Feb 7 - Feb 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
18.8/10 Exceptional! (1,838 reviews)
Great place …. Great people … very clean !!! And the breakfast was great !!!
Reviewed on Nov 8, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
Price was $4,502, price is now $2,487 per person
$2,487
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
18/10 Exceptional! (1,011 reviews)
Incredible staff, great accommodations, and literally right on the beach! And the restaurant is directly on the beach as well and he's definitely one of the better ones on the island
Reviewed on Nov 8, 2025
Don't see what you're looking for?
See all available trips from Columbus to Little Gasparilla Island
View all tripsDiscover the most popular places to visit in Little Gasparilla Island
Gasparilla Marina
Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this relaxing area.
Don Pedro Island State Park
Commune with nature and explore the great outdoors at Don Pedro Island State Park during your travels in Placida. Wander the beautiful beaches in this relaxing area.
What to do in Little Gasparilla Island
Little Gasparilla Island Hotel Deals

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $245 total per night from Nov 24 to Nov 25
$245 total
Nov 24 - Nov 25
Total with taxes and fees
9.2/10 Wonderful! (1,612 reviews)
How attentive the staff was and how clean the room was. 10/10
Reviewed on Nov 10, 2025

North Captiva Point House - Boat/Water Taxi Only **NEWLY RENOVATED **
North Captiva FL
9.4/10 Exceptional! (89 reviews)
The host was available day and night!
Reviewed on Oct 10, 2025

The Suites at Fishermen’s Village- 2 Bedroom Suites
1200 W Retta Esplanade Punta Gorda FL
Fully refundableReserve now, pay when you stay
$239 nightly
The price is $267 total per night from Nov 18 to Nov 19
$267 total
Nov 18 - Nov 19
Total with taxes and fees
9.6/10 Exceptional! (1,027 reviews)
Clean, beautiful decor, fully equipped suites . Fabulous Xmas decor going up. Loved the shops, bar and restaurants. Check in was a breeze, friendly employees everywhere.
Reviewed on Nov 15, 2025
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.
Find the Best Little Gasparilla Island Vacation Packages
Little Gasparilla Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Southwest Florida Intl. Airport (RSW) |
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