Little Gasparilla Island Vacation Packages 2026 from $498

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The Latest Little Gasparilla Island vacation packages

Price found within the past 48 hours. Click for updated prices.

Landing Apartments Fort Myers near Eastwood Village

Save 100% on your flight

$498

per person

Jan 10 - Jan 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (31 reviews)

This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 2026

The Perry Hotel Naples

Save 100% on your flight

$802

per person

Jan 7 - Jan 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,182 reviews)

Beautiful views

Reviewed on Oct 18, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$3,460

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,003 reviews)

GullWing Beach Resort

South Island

Save 100% on your flight

$886

per person

Jan 11 - Jan 15

found 14 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (976 reviews)

⭐️⭐️⭐️⭐️⭐️ I had a wonderful stay at this hotel! The staff was friendly, welcoming, and always ready to help. The room was clean, comfortable, and well-maintained, and the overall atmosphere was relaxing. The service was excellent, and everything made my stay enjoyable. I would definitely recommend this hotel to anyone looking for a comfortable and pleasant experience. I look forward to staying here again!

Reviewed on Oct 18, 2026

Edison Beach House

Save 100% on your flight

$1,470

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,921 reviews)

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Little Gasparilla Island Hotel Deals

Dream Beach House, steps to the Beach and beautiful Sunsets

Placida FL

10/10 Exceptional! (5 reviews)

"My short vacation on this island was wonderful."

Reviewed on Oct 4, 2026

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Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL

Fully refundableReserve now, pay when you stay

$208 nightly

$233 total

Nov 1 - Nov 2

Total with taxes and fees

9.2/10 Wonderful! (3,490 reviews)

"Beautiful pool and 3 bedroom villa was more than enough space for a family of 6."

Reviewed on Oct 19, 2026

The Suites at Fishermen’s Village

1200 W Retta Esplanade Punta Gorda FL

Fully refundableReserve now, pay when you stay

$175 nightly

$196 total

Oct 30 - Oct 31

Total with taxes and fees

9.8/10 Exceptional! (1,348 reviews)

"Exelent"

Reviewed on Oct 18, 2026

See all 6,359 properties in Little Gasparilla Island

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.