Search Deals on
Chokoloskee Vacation Packages

Build your package with 2 more options

Chokoloskee Flight + Hotel Packages

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 $860, price is now $547 per person
$547
per person
Aug 24 - Aug 29
found 17 hours ago
Roundtrip non-stop flight included
White Plains (HPN) 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.
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 $1,494, price is now $838 per person
$838
per person
Aug 24 - Aug 29
found 17 hours ago
Roundtrip non-stop flight included
White Plains (HPN) 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.
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $1,573, price is now $997 per person
$997
per person
Aug 31 - Sep 6
found 7 hours ago
Roundtrip non-stop flight included
Washington (IAD) 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.
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4 out of 5
Save 100% on your flight
Price was $1,095, price is now $713 per person
$713
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this beach condo in Englewood. Enjoy free WiFi, free parking, and 7 restaurants. Popular attractions Englewood Beach and Lemon Bay are located nearby.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Save 100% on your flight
Price was $859, price is now $567 per person
$567
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this spa resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Save 100% on your flight
Price was $1,012, price is now $698 per person
$698
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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 Bonita Springs Public Beach and Saltleaf Golf Preserve are located nearby.
A Wave From it All

A Wave From it All

2 out of 5
Save 100% on your flight
Price was $3,213, price is now $2,223 per person
$2,223
per person
Sep 1 - Sep 8
found 11 hours ago
Roundtrip flight included
Chicago (ORD) 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.
Bellasera Resort

Bellasera Resort

4 out of 5
Save 100% on your flight
Price was $1,160, price is now $804 per person
$804
per person
Aug 24 - Aug 29
found 17 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Fort Myers (RSW)
Book a stay at this business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Beach are located nearby.

Chokoloskee Vacation Packages 3-4 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 $867, price is now $636 per person
$636
per person
Sep 6 - Sep 10
found 3 hours ago
Roundtrip non-stop flight included
Washington (IAD) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Price was $933, price is now $695 per person
$695
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Washington (IAD) to Fort Myers (RSW)
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

3 out of 5
Price was $1,118, price is now $846 per person
$846
per person
Sep 6 - Sep 10
found 3 hours ago
Roundtrip non-stop flight included
Washington (IAD) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Price was $1,001, price is now $768 per person
$768
per person
Sep 6 - Sep 10
found 3 hours ago
Roundtrip non-stop flight included
Washington (IAD) 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 $860, price is now $547 per person
$547
per person
Aug 24 - Aug 29
found 17 hours ago
Roundtrip non-stop flight included
White Plains (HPN) 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 $1,494, price is now $838 per person
$838
per person
Aug 24 - Aug 29
found 17 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,573, price is now $997 per person
$997
per person
Aug 31 - Sep 6
found 7 hours ago
Roundtrip non-stop flight included
Washington (IAD) to Fort Myers (RSW)
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4 out of 5
Save 100% on your flight
Price was $1,095, price is now $713 per person
$713
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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
Wed, Aug 19 - Wed, Sep 2
ORD
O'Hare Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$82 Roundtrip, found 11 hours ago
$82
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Aug 19 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Sep 2, priced at $82 found 11 hours ago
Frontier Airlines
Tue, Aug 18 - Sat, Aug 29
ATL
Hartsfield-Jackson Atlanta Intl.
FLL
Fort Lauderdale - Hollywood Intl.
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Aug 29, priced at $98 just found
Frontier Airlines
Mon, Sep 14 - Mon, Sep 14
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$108 Roundtrip, found 7 hours ago
$108
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Mon, Sep 14, priced at $108 found 7 hours ago
Frontier Airlines
Wed, Aug 19 - Thu, Sep 10
PHL
Philadelphia Intl.
MIA
Miami Intl.
$117 Roundtrip, found 16 hours ago
$117
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Philadelphia Intl. to Miami Intl., returning Thu, Sep 10, priced at $117 found 16 hours ago