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Chokoloskee Vacation Packages

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A sunset over a body of water with two islands silhouetted against the sky.

Chokoloskee
Florida
United States of America
North America
Hotwire.com

Chokoloskee Flight + Hotel Packages

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

Tween Waters Island Resort & Spa

3 out of 5

Save 100% on your flight

Price was $821, price is now $510 per person

$510

per person

Dec 9 - Dec 12

found 13 hours ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Bowman's Beach and Captiva Beach are located nearby.

The Perry Hotel Naples

4.5 out of 5

Save 100% on your flight

Price was $1,693, price is now $908 per person

$908

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.

The Lighthouse Resort Inn & Suites

3 out of 5

Save 100% on your flight

Price was $961, price is now $627 per person

$627

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Key West Express and Times Square are located nearby.

The Light House Hotel location is amazing. It is across the street from Time Square, beach and next store to Margaritaville.

Reviewed on Oct 2, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5

Save 100% on your flight

Price was $2,390, price is now $1,560 per person

$1,560

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.

Olde Marco Island Inn and Suites

3 out of 5

Save 100% on your flight

Price was $886, price is now $625 per person

$625

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

Stay at this hotel in Marco Island. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Marco Beach and Pelican Pier Marina are located nearby.

Wiggins Pass Chalet

4 out of 5

Save 100% on your flight

Price was $926, price is now $664 per person

$664

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. Popular attractions Barefoot Beach and Vanderbilt Beach are located nearby.

Such a hidden gem in Naples! I’ve stayed here three weekends in a row and already have my next stay planned in two weeks. The rooms are incredibly clean, modern, comfortable and have everything you need. The staff is always friendly and welcoming, and it truly feels more like staying in a beautiful little condo than a hotel. I’m so happy I found this place — it has officially become my go-to whenever I’m in Naples. Highly recommend! ⭐️⭐️⭐️⭐️⭐️

Reviewed on Oct 1, 2026

Casa Ybel Resort

2.5 out of 5

Price was $1,043, price is now $765 per person

$765

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Sanibel Island Southern Beach and Bowman's Beach are located nearby.

Landing Furnished Apartments Immokalee Road - Naples

4 out of 5

Save 100% on your flight

Price was $1,030, price is now $757 per person

$757

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Fort Myers (RSW)

Book a stay at this golf apartment in Naples. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Arrowhead Golf Course and Quail Village Golf Club are located nearby.