Vacations in Southwest Florida

Vacations in Southwest Florida

2 travelers

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Cheap Southwest Florida package deals

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$178 - $537$537 - $896$896 - $1,255$1,255 - $1,614$1,614+ per night

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Most popular Southwest Florida flight and hotel deals

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Travelodge by Wyndham Fort Myers Airport - Fort Myers - Building
Travelodge by Wyndham Fort Myers Airport - Fort Myers - Building
Travelodge by Wyndham Fort Myers Airport
6.7 Okay
Parking
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$177
TownePlace Suites by Marriott Fort Myers Southeast - Fort Myers - Lounge
TownePlace Suites by Marriott Fort Myers Southeast - Fort Myers - Lounge
TownePlace Suites by Marriott Fort Myers Southeast
8.1 Very good
Omni
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$276
Americas Best Value Inn Fort Myers - Fort Myers - Pool
Americas Best Value Inn Fort Myers - Fort Myers - Pool
Americas Best Value Inn Fort Myers
7.1 Good
Parking
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$200
Vistas Eastwood Apartments by Barsala - Fort Myers - Pool
Vistas Eastwood Apartments by Barsala - Fort Myers - Pool
Vistas Eastwood Apartments by Barsala
10 Wonderful
Eastwood Village
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$574
Extended Stay America Premier Suites - Fort Myers - Airport - Fort Myers - Bedroom
Extended Stay America Premier Suites - Fort Myers - Airport - Fort Myers - Bedroom
Extended Stay America Premier Suites - Fort Myers - Airport
8.3 Very good
Parking
Free Wi-Fi
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$221
Candlewood Suites Ft Myers I-75 - Fort Myers - Lobby
Candlewood Suites Ft Myers I-75 - Fort Myers - Lobby
Candlewood Suites Ft Myers I-75
7.5 Good
Omni
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$220
Summerwind Studios - Fort Myers - Pool
Summerwind Studios - Fort Myers - Pool
Summerwind Studios
7.5 Good
Parking
Free Wi-Fi
Chicago O'Hare Intl
Meals not included
3 nights + flight
$237
Red Roof PLUS+ Fort Myers - Fort Myers - Bedroom
Red Roof PLUS+ Fort Myers - Fort Myers - Bedroom
Red Roof PLUS+ Fort Myers
6.7 Okay
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$204
TownePlace Suites by Marriott Fort Myers Gulf Coast - Fort Myers - Bedroom
TownePlace Suites by Marriott Fort Myers Gulf Coast - Fort Myers - Bedroom
TownePlace Suites by Marriott Fort Myers Gulf Coast
8.9 Very good
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$293
Brand New Coral Reef Suite Located in Paradise Island Estate - Fort Myers
Brand New Coral Reef Suite Located in Paradise Island Estate - Fort Myers
Brand New Coral Reef Suite Located in Paradise Island Estate
Free Wi-Fi
Indianapolis
Meals not included
3 nights + flight
$723
Brand New Tropical Studio Villa With Resort Amenities Boaters Gulf Access Outdoor Kitchen Lagoon Lazy River Pool - Fort Myers
Brand New Tropical Studio Villa With Resort Amenities Boaters Gulf Access Outdoor Kitchen Lagoon Lazy River Pool - Fort Myers
Brand New Tropical Studio Villa With Resort Amenities Boaters Gulf Access Outdoor Kitchen Lagoon Lazy River Pool
Parking
Free Wi-Fi
Indianapolis
Meals not included
3 nights + flight
$684
Hampton Inn Fort Myers Downtown - Fort Myers - Bedroom
Hampton Inn Fort Myers Downtown - Fort Myers - Bedroom
Hampton Inn Fort Myers Downtown
8.3 Very good
Altamont Manor
Pool
Chicago O'Hare Intl
Breakfast
3 nights + flight
$231
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway - Fort Myers - Building
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway - Fort Myers - Building
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway
7.5 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Chicago O'Hare Intl
Breakfast
3 nights + flight
$207
Hampton Inn Ft. Myers-Airport I-75 - Fort Myers - Pool
Hampton Inn Ft. Myers-Airport I-75 - Fort Myers - Pool
Hampton Inn Ft. Myers-Airport I-75
8.6 Very good
Parking
Airport shuttle
Free Wi-Fi
Pool
Chicago O'Hare Intl
Breakfast
3 nights + flight
$238
Woodspring Suites Fort Myers - Cape Coral - Fort Myers - Building
Woodspring Suites Fort Myers - Cape Coral - Fort Myers - Building
Woodspring Suites Fort Myers - Cape Coral
7.1 Good
Parking
Pet friendly
Chicago O'Hare Intl
Meals not included
3 nights + flight
$219
Tip Top Isles Waterfront Resort & Marina - Fort Myers - Patio
Tip Top Isles Waterfront Resort & Marina - Fort Myers - Patio
Tip Top Isles Waterfront Resort & Marina
Boston Logan Intl
Breakfast
3 nights + flight
$381

Last minute vacation packages to Southwest Florida

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Bali Hai Beachfront Resort and Spa - Anna Maria - Dining room
Bali Hai Beachfront Resort and Spa - Anna Maria - Dining room
Bali Hai Beachfront Resort and Spa
7.9 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Lambert-St Louis
Meals not included
3 nights + flight
$1,174
Buttonwood Cottage - Anna Maria - Pool
Buttonwood Cottage - Anna Maria - Pool
Buttonwood Cottage
Parking
Free Wi-Fi
Pool
Pet friendly
Lambert-St Louis
Meals not included
3 nights + flight
$1,828
DoubleTree by Hilton Sarasota Bradenton Airport - Sarasota - Patio
DoubleTree by Hilton Sarasota Bradenton Airport - Sarasota - Patio
DoubleTree by Hilton Sarasota Bradenton Airport
7.8 Good
Parking
Airport shuttle
Free Wi-Fi
Pool
Lambert-St Louis
Meals not included
3 nights + flight
$563
Kompose Hotel - Sarasota - Living room
Kompose Hotel - Sarasota - Living room
Kompose Hotel
8.6 Very good
Free Wi-Fi
Pool
Pet friendly
Lambert-St Louis
Meals not included
3 nights + flight
$539

When to book a vacation in Southwest Florida

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Where to stay in Southwest Florida

Our map will help you find the perfect place to stay for your vacation in Southwest Florida by showing you the exact location of each hotel.

Everything you need to know for your vacation in Southwest Florida

Southwest Florida vacation: Search Southwest Florida vacation packages on KAYAK. KAYAK is a travel tool that searches Southwest Florida trips on hundreds of travel sites to help you find the Southwest Florida package that suits you best. Discover Southwest Florida deals now and book your Southwest Florida flight and hotel today.

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