Southwest Florida Vacations from $410
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Your Southwest Florida Vacation
Set off on your next big adventure with a Southwest Florida vacation package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customize your escape, you know it'll be one to remember. Begin your trip to Southwest Florida with a couple of days in Tampa visiting popular attractions like Busch Gardens Tampa Bay and Raymond James Stadium. Sarasota is another top city that lures crowds from near and far. Bay Island and Siesta Key Beach are two of the leading places to see here. From the moment you book your Southwest Florida vacation to the second you come back home, Expedia has you covered each step of the way.
The Latest Southwest Florida Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Casa Boutique Hotel
South Beach
Save 100% on your flight
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,025 reviews)
We stay at the Hotel with my family, 2 adults and 2 kids. The room was good, maybe the wardrobe was a little small for all of us. The location is excellent, only 3 blocks from the beach and the main streets. Lincon and Ocean has a unique vibe and the night is awesome. The staff was very polite and responds to our questions, you have a public park 2 blocks away where you can leave the car paying accordly, not expensive. The Hotel shares the front of the facility with a very cute restaurant. If you go to south beach is a really good option.
Reviewed on May 1, 2025
Fontainebleau Miami Beach
Mid Beach
Save 100% on your flight
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (5,944 reviews)
Everything was on point I love and enjoyed everything about it to the reception to the housekeeping everything
Reviewed on May 2, 2025
Ocean Club Treasure Island Hotel
Save 100% on your flight
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (386 reviews)
Very nice place and facilities! Staff was very friendly and accommodating to our needs with our luggage and etc. Beds were very comfortable and place was very clean! We had a great time!
Reviewed on Apr 28, 2025
Where to stay in Southwest Florida
Find the best Southwest Florida areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Florida
South End
While visiting South End, you might make a stop by sights like South Marco Beach and Marco Island Ski & Watersports.
Find the Best Southwest Florida Vacation Packages
Southwest Florida Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tampa Intl. Airport (TPA) |
Southwest Florida Hotel Deals
Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
The price is $344 per night from Jun 1 to Jun 2
$344
includes taxes & fees
$310 per night
Jun 1 - Jun 2
8.8/10 Excellent! (1,452 reviews)
"Rooms are a bit outdated, but generally a great place to stay with direct beach access."
Reviewed on Apr 30, 2025
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
The price is $317 per night from May 12 to May 13
$317
includes taxes & fees
$284 per night
May 12 - May 13
8.8/10 Excellent! (1,037 reviews)
"I loved this resort! It was modern, clean, staff was friendly, I could walk around the area safely, the pool was beautiful. It was a fun, relaxed atmosphere. I’d definitely recommend! Orbitz on the other hand made billing tricky. I thought the trip was paid for but some charges came from the hotel ..."
Reviewed on May 1, 2025
Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is $214 per night from May 19 to May 20
$214
includes taxes & fees
$189 per night
May 19 - May 20
9.2/10 Wonderful! (4,637 reviews)
"The hotel is next to the beach, walking to the beach is easy. A lot of dinning options just several minutes walking away. Even due to cutting the tree we couldn’t park the car next to our room, but the staff offered parking very close by. Front desk was very nice and helpful as well."
Reviewed on Apr 29, 2025
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.
Discover the most popular places to visit in Southwest Florida
Siesta Key Beach
4.5/5(1,425 reviews)
The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.
Lido Beach
4.5/5(1,225 reviews)
Visit a beach not far from an upscale shopping area. The warm waters are as inviting as the white sand.
St. Armands Circle
4.5/5(1,234 reviews)
Consider this area as a circular outdoor mall. Like any mall, you can shop, dine, browse or just people-watch. Unlike most malls, this one never closes to walkers.
What to do in Southwest Florida
Private Snorkeling Adventure with the Ultimate Local Expert
$110
per adult
96% of travellers recommend
Guided Snorkel Experience, Free Videos in West Palm Beach
$45
per adult
Scenic Sunset Cruise in West Palm Beach
$51
per adult
94% of travellers recommend
Explore a world of travel with Expedia
Lodging
- Hotels near Old Corkscrew Golf Club
- Hotels near Stoneybrook
- Gay friendly Hotels in Stoneybrook
- Hotels near Stoneybrook Golf Club
- Hotels near Miromar Outlets
- Hotels near Hertz Arena
- Hotels near Alico Arena
- Hotels near Corkscrew Woodlands
- Gay friendly Hotels near Corkscrew Woodlands
- Hotels near Florida Gulf Coast University
- Hotels near Corkscrew Swamp Sanctuary
- Hotels near Miromar Lakes
- Luxury Hotels near Miromar Lakes
- Waterpark Hotels in Miromar Lakes
- 4 Star Hotels in Miromar Lakes
- Casino Hotels in Miromar Lakes
- Boutique Hotels near Miromar Lakes
- Oceanfront Hotels in Miromar Lakes
- Business Hotels near Miromar Lakes
- Independent Hotels in Miromar Lakes
- Hyatt Hotels in Miromar Lakes
- Hotels near Southwest Florida Intl.
- Estero Hotels
- Cheap Hotels in Estero
- Beach Hotels in Estero
- Condo Rentals in Estero
- Pet-friendly Hotels in Estero
- Hotels with Balconies in Estero
- La Quinta Inn & Suites Hotels in Estero
- Extended Stay Hotels in Estero
- Luxury Hotels in Estero
- Golf Hotels in Estero
- 4 Star Hotels in Estero
- 5 Star Hotels in Estero
- Resorts & Hotels with Spas in Estero
- Villas in Estero
- Family Hotels in Estero
- Hotels with a Gym in Estero
- Aparthotels in Estero
- 3 Star Hotels in Estero
- Hotels with a Pool in Estero
- Hotels with Laundry Facilities in Estero
- Hotels with Bars in Estero
- Resorts in Estero
- Hotels with Free Breakfast in Estero
- Hotels with Restaurants in Estero
- Motels in Estero
- Vacation Homes in Estero
- Romantic Hotels in Estero
- Hotels with Hot Tubs in Estero
Flights
- Flights from Southwest Florida Intl.
- Flights from Chicago (ORD) to Fort Myers (RSW)
- Flights from Boston (BOS) to Fort Myers (RSW)
- Flights from Minneapolis (MSP) to Fort Myers (RSW)
- Flights from Philadelphia (PHL) to Fort Myers (RSW)
- Flights from Detroit (DTW) to Fort Myers (RSW)
- Flights from Cleveland (CLE) to Fort Myers (RSW)
- Flights from New York (NYC) to Fort Myers (RSW)
- Flights to Estero
- Flights from Milwaukee (MKE) to Fort Myers (RSW)
- Flights from Pittsburgh (PIT) to Fort Myers (RSW)
- Flights from Estero
Cars
- Car rental Fort Myers Airport (RSW)
- Car rentals near Miromar Outlets
- Car rentals near Alico Arena
- Car rentals near Hertz Arena
- Van Car Rentals near Hertz Arena
- Fullsize Car Rentals near Hertz Arena
- Car rentals near Florida Gulf Coast University
- Car rentals near Corkscrew Swamp Sanctuary
- Hertz Rental Cars in Miromar Lakes
- Budget Rental Cars in Miromar Lakes
- Right Cars Rental Cars in Miromar Lakes
- Advantage Rent-A-Car Rental Cars in Miromar Lakes
- Standard Car Rentals in Miromar Lakes
- Top Rent a Car Rental Cars in Miromar Lakes
- Smile Rental Cars in Miromar Lakes
- Click & Rent Rental Cars in Miromar Lakes
- Express Travel Group Rental Cars in Miromar Lakes
- Car rentals near Three Oaks
- Car rentals near Estero
- Budget Rental Cars in Estero
- Hertz Rental Cars in Estero
- National Car Rental Rental Cars in Estero
- Enterprise Rental Cars in Estero
- Thrifty Car Rental Rental Cars in Estero
Vacation Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.