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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.
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $994, price is now $654 per person
$654
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
Springfield (SGF) to Fort Myers (RSW)
Book a stay at this beach hotel in Englewood. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Englewood Beach and Stump Pass Beach State Park are located nearby.
Love the location of this property, the amenities and the accommodating staff.

Reviewed on Nov 14, 2026

Southseas

Southseas

3 out of 5
Price was $3,951, price is now $2,550 per person
$2,550
per person
Feb 3 - Feb 10
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach apartment in Marco Island. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Tigertail Beach and Marco Beach are located nearby.

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,105, price is now $716 per person
$716
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Loved the stay while we were there, security was convenient so we felt safe. The only thing and it’s not really a negative thing it’s just the rooftop pool is right next to the rooftop restaurant. So while people are eating, they see you half naked swimming but other than that the stay was great. Will definitely come back and I encourage others to come here as well. Fabulous getaway for couples.

Reviewed on Nov 15, 2026

Olde Marco Island Inn and Suites

Olde Marco Island Inn and Suites

3 out of 5
Price was $2,253, price is now $1,529 per person
$1,529
per person
Feb 3 - Feb 10
found 7 hours 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 Tigertail Beach and Marco Beach are located nearby.
The property is very nice with several on site restaurants and a decent bar and club for late nights. Its definitely for the older crowd but very enjoyable. The main bar and restaurant however is condemned and the whole property is going to be raised and replaced soon.

Reviewed on Nov 8, 2026

Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach

Marco Polo by Avantstay Waterfront 5bdr, Pool, Spa, Fire Pit, Walk to Beach

3 out of 5
Price was $11,623, price is now $7,890 per person
$7,890
per person
Feb 3 - Feb 10
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this cottage in Marco Island. Enjoy free parking, private pools, and a beach locale. Popular attractions South Marco Beach and Marco Beach are located nearby.

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $1,510, price is now $1,033 per person
$1,033
per person
Feb 5 - Feb 8
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.

GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
Price was $1,764, price is now $1,218 per person
$1,218
per person
Jan 24 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Bonita Springs Public Beach are located nearby.
Beautiful property, generous size condos and all the amenities.

Reviewed on Nov 6, 2026

Chokoloskee Vacation Packages 3-4 Night Stays

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

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $994, price is now $654 per person
$654
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
Springfield (SGF) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $1,105, price is now $716 per person
$716
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $1,510, price is now $1,033 per person
$1,033
per person
Feb 5 - Feb 8
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Wiggins Pass Chalet

Wiggins Pass Chalet

4 out of 5
Price was $924, price is now $667 per person
$667
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Chokoloskee Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $2,081, price is now $1,247 per person
$1,247
per person
Jan 21 - Jan 26
found 21 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $4,142, price is now $2,526 per person
$2,526
per person
Jan 21 - Jan 26
found 21 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Bellasera Resort

Bellasera Resort

4 out of 5
Downtown
Price was $4,441, price is now $2,811 per person
$2,811
per person
Feb 3 - Feb 10
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Southseas

Southseas

3 out of 5
Price was $3,951, price is now $2,550 per person
$2,550
per person
Feb 3 - Feb 10
found 7 hours ago
Roundtrip flight included
Boston (BOS) 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
Mon, Feb 1 - Thu, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$48 Roundtrip, just found
$48
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Feb 1 from Hartsfield-Jackson Atlanta Intl. to Fort Lauderdale - Hollywood Intl., returning Thu, Feb 4, priced at $48 just found
Frontier Airlines
Sat, Dec 5 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$58 Roundtrip, found 3 hours ago
$58
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Tue, Dec 8, priced at $58 found 3 hours ago
Frontier Airlines
Tue, Feb 16 - Tue, Feb 23
DTW
Detroit Metropolitan Wayne County
MIA
Miami Intl.
$78 Roundtrip, found 5 hours ago
$78
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Feb 16 from Detroit Metropolitan Wayne County to Miami Intl., returning Tue, Feb 23, priced at $78 found 5 hours ago
Frontier Airlines
Mon, Jan 25 - Thu, Feb 4
PHL
Philadelphia Intl.
MIA
Miami Intl.
$79 Roundtrip, found 1 day ago
$79
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jan 25 from Philadelphia Intl. to Miami Intl., returning Thu, Feb 4, priced at $79 found 1 day ago