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Villas Vacation Packages

Villas Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
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 $831, price is now $553 per person
$553
per person
May 23 - May 27
found 19 hours ago
Roundtrip flight included
Boston (BOS) 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.
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 $1,911, price is now $1,043 per person
$1,043
per person
May 27 - May 31
found 24 hours ago
Roundtrip flight included
Boston (BOS) 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.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,018, price is now $674 per person
$674
per person
May 27 - May 31
found 24 hours 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.
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 $1,285, price is now $868 per person
$868
per person
May 24 - May 28
found 1 day 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.
The Boat House

The Boat House

2 out of 5
Olde Marco
Save 100% on your flight
Price was $1,285, price is now $902 per person
$902
per person
May 21 - May 28
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Marco Island. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pelican Pier Marina and Cannon Beach are located nearby.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $997, price is now $713 per person
$713
per person
May 27 - May 31
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. 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.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $1,079, price is now $776 per person
$776
per person
May 22 - May 26
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and daily housekeeping. 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.
Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,170, price is now $854 per person
$854
per person
May 15 - May 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

3-4 Night Vacations in Villas

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $552, price is now $378 per person
$378
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $642, price is now $438 per person
$438
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
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 $837, price is now $579 per person
$579
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Price was $612, price is now $428 per person
$428
per person
May 12 - May 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

5-7 Night Vacations in Villas

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Price was $1,075, price is now $767 per person
$767
per person
May 21 - May 26
found 18 hours ago
Roundtrip non-stop flight included
Islip (ISP) 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 $2,987, price is now $1,576 per person
$1,576
per person
May 16 - May 23
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,280, price is now $791 per person
$791
per person
May 16 - May 23
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
The Boat House

The Boat House

2 out of 5
Olde Marco
Save 100% on your flight
Price was $1,285, price is now $902 per person
$902
per person
May 21 - May 28
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Cheap Hotel Deals in Villas

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
12600 University Dr Fort Myers FL
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Opens in a new windowHilton Garden Inn Ft Myers
Doubletree by Hilton Fort Myers at Bell Tower Shops

Doubletree by Hilton Fort Myers at Bell Tower Shops

4 out of 5
13051 Bell Tower Drive Fort Myers FL
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Opens in a new windowDoubletree by Hilton Fort Myers at Bell Tower Shops
Homewood Suites by Hilton - Fort Myers

Homewood Suites by Hilton - Fort Myers

3 out of 5
5255 Big Pine Way Fort Myers FL
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowHomewood Suites by Hilton - Fort Myers
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Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

2.5 out of 5
1538 Cape Coral Pkwy E Cape Coral FL
Book a stay at this business-friendly hotel in Cape Coral. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Opens in a new windowHoliday Inn Express Cape Coral-Fort Myers Area by IHG
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
Opens in a new windowMargaritaville Beach Resort Fort Myers
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr Sanibel FL
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
Opens in a new windowSanibel Island Beach Resort
Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

2.5 out of 5
4850 S Cleveland Ave Fort Myers FL
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowBaymont by Wyndham Fort Myers Central
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Estero Boulevard ...
Opens in a new windowLani Kai Beachfront Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

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

Frontier Airlines
Mon, May 4 - Wed, May 20
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$102 Roundtrip, found 12 hours ago
$102
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Mon, May 4 from Hopkins Intl. to Southwest Florida Intl., returning Wed, May 20, priced at $102 found 12 hours ago
Frontier Airlines
Sun, May 3 - Sat, May 16
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$117 Roundtrip, found 5 hours ago
$117
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, May 3 from O'Hare Intl. to Southwest Florida Intl., returning Sat, May 16, priced at $117 found 5 hours ago
Spirit Airlines
Tue, Apr 28 - Tue, May 12
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$192 Roundtrip, found 14 hours ago
$192
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Logan Intl. to Southwest Florida Intl., returning Tue, May 12, priced at $192 found 14 hours ago
United
Sat, May 2 - Wed, May 13
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$197 Roundtrip, found 16 hours ago
$197
Roundtrip
found 16 hours ago
Select United flight, departing Sat, May 2 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Wed, May 13, priced at $197 found 16 hours ago