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Chokoloskee Vacation Packages

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Chokoloskee Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Landing Fort Myers Near Highland Pines

Landing Fort Myers Near Highland Pines

4 out of 5
Save 100% on your flight
Price was $1,097, price is now $746 per person
$746
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this aparthotel in Fort Myers. Enjoy free WiFi, free parking, and a fitness center. Popular attractions JetBlue Park at Fenway South and Six Mile Cypress Slough Preserve are located nearby.
Very Clean

Reviewed on Sep 9, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,167, price is now $1,379 per person
$1,379
per person
Nov 16 - Nov 22
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 Delnor-Wiggins Pass State Park and Vanderbilt Beach are located nearby.
The hotel is new. Rooms are very spacious. Hotel pool is cute, although small. The boat ride to the beach is a nice touch but keep in mind you must reserve ahead of time. Having the coffee shop in the lobby was convenient. The location is a bit weird behind a small shopping center.

Reviewed on Sep 26, 2026

Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
Save 100% on your flight
Price was $1,606, price is now $1,037 per person
$1,037
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this beach condo in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $3,822,303, price is now $2,498,976 per person
$2,498,976
per person
Dec 4 - Dec 11
found 1 day 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.

Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was $1,263, price is now $841 per person
$841
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this apartment in Fort Myers. Enjoy in-room washers/dryers, an in-room coffeemaker, and air conditioning. Popular attractions JetBlue Park at Fenway South and Calusa Nature Center and Planetarium are located nearby.
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

Wiggins Pass Chalet

Wiggins Pass Chalet

4 out of 5
Save 100% on your flight
Price was $1,292, price is now $873 per person
$873
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Delnor-Wiggins Pass State Park and Barefoot Beach are located nearby.

Landing Furnished Apartments minutes from Downtown Fort Myers

Landing Furnished Apartments minutes from Downtown Fort Myers

3 out of 5
Save 100% on your flight
Price was $1,419, price is now $968 per person
$968
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Stay at this apartment in North Fort Myers. Enjoy an outdoor pool, a fitness center, and an in-room coffeemaker. Popular attractions Art of the Olympians Museum and Caloosa Sound Amphitheater are located nearby.
I enjoyed my stay. It was clean and roomy. They proved complimentary laundry pods, dish washer pods, dish soap etc. I enjoyed sitting on the balcony drinking my coffee. The pool and pool area was beautiful. I wish, they'd give one access code for the whole stay not asign one each day. I'd stay there again.

Reviewed on Sep 21, 2026

Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,418, price is now $971 per person
$971
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
The view from our balcony was amazing, room was clean and beds were comfy. Staff were friendly. Just check your final bill carefully as we were charged for fees not previously disclosed.

Reviewed on Sep 25, 2026

Chokoloskee Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was $814, price is now $574 per person
$574
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,673, price is now $1,093 per person
$1,093
per person
Dec 8 - Dec 12
found 17 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Price was $1,005, price is now $745 per person
$745
per person
Dec 8 - Dec 12
found 17 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Price was $972, price is now $722 per person
$722
per person
Dec 8 - Dec 12
found 17 hours ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)

Chokoloskee Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Landing Apartments Fort Myers near Eastwood Village

Landing Apartments Fort Myers near Eastwood Village

3 out of 5
Save 100% on your flight
Price was $1,263, price is now $841 per person
$841
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,118, price is now $1,233 per person
$1,233
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

3 out of 5
South Island
Save 100% on your flight
Price was $1,606, price is now $1,037 per person
$1,037
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $3,822,303, price is now $2,498,976 per person
$2,498,976
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Nov 3 - Tue, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Nov 3 from Hartsfield-Jackson Atlanta Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Nov 10, priced at $80 just found
Frontier Airlines
Tue, Nov 3 - Thu, Nov 12
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Nov 3 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Thu, Nov 12, priced at $80 found 1 hour ago
Frontier Airlines
Tue, Nov 17 - Thu, Dec 3
PHL
Philadelphia Intl.
MIA
Miami Intl.
$99 Roundtrip, found 1 hour ago
$99
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Philadelphia Intl. to Miami Intl., returning Thu, Dec 3, priced at $99 found 1 hour ago
Allegiant Air
Sun, Nov 8 - Thu, Nov 12
TTN
Mercer
FLL
Fort Lauderdale - Hollywood Intl.
$104 Roundtrip, found 1 hour ago
$104
Roundtrip
found 1 hour ago
Select Allegiant Air flight, departing Sun, Nov 8 from Mercer to Fort Lauderdale - Hollywood Intl., returning Thu, Nov 12, priced at $104 found 1 hour ago