Southwest Florida Vacations from $362

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The Latest Southwest Florida Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
East Fort Lauderdale
per person
Jul 17 - Jul 22
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (72 reviews)
I love this property, I will come back. They have everything that I need. I have a relaxing weekend.

Reviewed on Jun 1, 2024

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9/10 Wonderful! (1,004 reviews)
Beautiful property, the rooftop pool steals the show.

Reviewed on Jun 6, 2024

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Jul 25 - Jul 29
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
Jul 10 - Jul 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.2/10 Very Good! (1,002 reviews)
Property is in a very good area and great tourist spot. A great place for any kimd of activities you are looking for. And a great spot very close to the beach. Very recommended hotel.

Reviewed on Jun 3, 2024

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
per person
Jul 10 - Jul 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (647 reviews)
Great location and so close to the beach. You can walk on Ocean drive and explore the streets without being far from the hotel.

Reviewed on Jun 1, 2024

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
Siesta Key Village

Siesta Key Village

4.5/5(282 area reviews)

Tropical colored buildings, lots of sandy beaches and a compact shopping area make this village a good choice to visit and stay. Enjoy an on-going social life too.

Find hotel + flight trips in Siesta Key Village

Southwest Florida Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tampa Intl. Airport (TPA)

Southwest Florida Hotel Deals

Kompose Boutique Hotel
Kompose Boutique Hotel
3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is $78 per night from Jun 9 to Jun 10
$78
$102 total
includes taxes & fees
Jun 9 - Jun 10
8.8/10 Excellent! (3,461 reviews)
"Brand new. Cute . Chic and friendly"

Reviewed on Jun 6, 2024

Kompose Boutique Hotel
Hyatt Regency Sarasota
Hyatt Regency Sarasota
4 out of 5
1000 Blvd Of The Arts, Sarasota, FL
Fully refundable
The price is $159 per night from Jun 9 to Jun 10
$159
$214 total
includes taxes & fees
Jun 9 - Jun 10
8/10 Very Good! (1,014 reviews)
"Bathroom is really small with a sulfer smell when you flush."

Reviewed on Jun 2, 2024

Hyatt Regency Sarasota
The Westin Sarasota
The Westin Sarasota
4 out of 5
100 Marina View Drive, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is $178 per night from Jun 23 to Jun 24
$178
$223 total
includes taxes & fees
Jun 23 - Jun 24
8.6/10 Excellent! (1,017 reviews)
"Nice location and staff. Will stay again."

Reviewed on Jun 3, 2024

The Westin Sarasota
See all 42,742 properties in Southwest Florida
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Southwest Florida vacation package cost?
Less than you might think — from just $362, in fact! By bundling flights, hotels and car rentals into your own custom-built vacation package, your getaway to Southwest Florida is just a few clicks away.
How do I get a cheap travel package to Southwest Florida?
Browse and book everything in the one place with our Southwest Florida vacation packages. We have incredible bargains on flights, hotels and more that’ll keep your pocket happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties worldwide to select from, you’ll have the flexibility to mix and match all you want.
Where should I stay in Southwest Florida?
You can’t go past Tampa, with terrific landmarks including Raymond James Stadium and University of South Florida to discover. Or, if sights like Edison and Ford Winter Estates and Sun Splash Water Park are more your scene, Fort Myers is the place for you.
What are the top hotels in Southwest Florida?
Naples Grande Beach Resort and La Quinta Inn & Suites by Wyndham Naples East (I-75) know how to make their guests feel welcome in Naples. If your itinerary also includes Cape Coral, take a look at Trianon Bonita Bay and Sanibel Island Beach Resort. Both are very popular with travelers.
How far in advance should I book my Southwest Florida vacation?
Get rewarded with the widest variety at the cheapest prices by booking your vacation to Southwest Florida nice and early. Air carriers generally advertise tickets around a year before departure, so reserve your spot as soon as possible. That being said, Expedia is dedicated to providing you with the best deals around, so there’s never a bad time to book your dream vacation!
What does an Expedia Southwest Florida travel package include?
That mostly depends on you. You can select from a range of Southwest Florida bundles, such as a flight, hotel and rental car. You can also book a hotel and a flight, or a flight and a rental car. Once you’ve made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Southwest Florida vacation looks like, you’re sure to save!
What should I know before booking a Southwest Florida travel package?
You can save a tidy sum by combining your flights, hotels and rental cars. Once you’ve made your booking, add on fun stuff like activities or tours. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Southwest Florida Expedia vacation package?
Yes — that’s the beauty of an Expedia package. You’re the boss! We have access to more than 550 partner airlines all over the world, so you have options galore when putting together your Southwest Florida escape.
If I'm not able to travel, can I cancel my Southwest Florida vacation package?
It’s hard to predict what the future holds, so it’s good to know that you can cancel or change your Southwest Florida vacation package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Southwest Florida

Image for Siesta Key Beach

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.

Siesta Key Beach
Image for John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the seaside in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Image for Lido Beach

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.

Lido Beach

What to do in Southwest Florida

Image for Scenic Sunset Cruise in West Palm Beach

Scenic Sunset Cruise in West Palm Beach

$51
Per adult
92% of travellers recommend
Scenic Sunset Cruise in West Palm Beach
Image for Historical Sightseeing Catamaran Cruise in Palm Beach

Historical Sightseeing Catamaran Cruise in Palm Beach

$51
Per adult
92% of travellers recommend
Historical Sightseeing Catamaran Cruise in Palm Beach
Image for 3 Hour Cruise & Swimming Excursion off Peanut Island Park

3 Hour Cruise & Swimming Excursion off Peanut Island Park

$77
Per adult
3 Hour Cruise & Swimming Excursion off Peanut Island Park
See all activities in Southwest Florida

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.