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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.
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $823, price is now $536 per person
$536
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Sanibel Island Lighthouse are located nearby.
Ŵe were very pleased. Restaurant was very good. We didnt use the pool or beach but both looked well maintained. Didnt realized there were stairs. Should be cautioned. Grounds man helped with luggage going up but busy checkout when we left . $40 per day charge for beach umbrellas and chairs. Overall, a great four days

Reviewed on Jul 27, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Save 100% on your flight
Price was $1,761, price is now $923 per person
$923
per person
Oct 21 - Oct 25
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Delnor-Wiggins Pass State Park are located nearby.

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,011, price is now $603 per person
$603
per person
Oct 21 - Oct 25
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Delnor-Wiggins Pass State Park are located nearby.

GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,435, price is now $893 per person
$893
per person
Sep 30 - Oct 7
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 Estero Boulevard Beach are located nearby.
Excelente servicio, calidad, comodidad, precio y ubicación

Reviewed on Jul 26, 2026

A Wave From it All

A Wave From it All

2 out of 5
Save 100% on your flight
Price was $2,661, price is now $1,744 per person
$1,744
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)
Stay at this vacation home in Fort Myers Beach. Enjoy free WiFi, free parking, and 6 beach bars. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.

Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,330, price is now $886 per person
$886
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Another great stay at Tween Waters!

Reviewed on Jul 26, 2026

Latitude 26 Waterfront Resort & Marina

Latitude 26 Waterfront Resort & Marina

3 out of 5
Save 100% on your flight
Price was $933, price is now $647 per person
$647
per person
Oct 17 - Oct 24
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this motel in Fort Myers Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Staff were phenomenal! The rooms were so trendy, decorative, and artsy. Breakfast was fresh, the bar was open during the day, and the entire property was super clean!

Reviewed on Jul 27, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Price was $1,125, price is now $783 per person
$783
per person
Oct 8 - Oct 13
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this aparthotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage Museum are located nearby.
Beautiful suite

Reviewed on Jul 27, 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 $751, price is now $454 per person
$454
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $1,761, price is now $923 per person
$923
per person
Oct 21 - Oct 25
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,011, price is now $603 per person
$603
per person
Oct 21 - Oct 25
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $823, price is now $536 per person
$536
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $893, price is now $592 per person
$592
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Save 100% on your flight
Price was $1,564, price is now $971 per person
$971
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
South Island
Save 100% on your flight
Price was $1,435, price is now $893 per person
$893
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
A Wave From it All

A Wave From it All

2 out of 5
Siesta Isle
Save 100% on your flight
Price was $2,661, price is now $1,744 per person
$1,744
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Fort Myers (RSW)

Top Flight Deals

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

Allegiant Air
Thu, Oct 29 - Thu, Nov 5
TTN
Mercer
FLL
Fort Lauderdale - Hollywood Intl.
$78 Roundtrip, found 5 hours ago
$78
Roundtrip
found 5 hours ago
Select Allegiant Air flight, departing Thu, Oct 29 from Mercer to Fort Lauderdale - Hollywood Intl., returning Thu, Nov 5, priced at $78 found 5 hours ago
Frontier Airlines
Tue, Sep 22 - Thu, Sep 24
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Sep 22 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Thu, Sep 24, priced at $80 just found
Frontier Airlines
Wed, Aug 19 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Aug 19 from Hartsfield-Jackson Atlanta Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Sep 1, priced at $82 just found
Allegiant Air
Thu, Oct 1 - Thu, Oct 8
SWF
Stewart Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$86 Roundtrip, found 3 days ago
$86
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Oct 1 from Stewart Intl. to Fort Lauderdale - Hollywood Intl., returning Thu, Oct 8, priced at $86 found 3 days ago