Southwest Florida Holidays

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Our guide on 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
A clear turquoise sea, a sandy beach, and a rocky outcrop with palm trees.

North Captiva

Visitors to North Captiva enjoy its beaches, and if you want to do some exploring, North Captiva Island Beach is worth a stop.

Find hotels in North Captiva

Southwest Florida Holiday

Our pick of the best 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 NZ$148 per night from 14 July to 15 July
NZ$148
14 July - 15 July
includes taxes & fees
9.2/10 Wonderful! (5,655 reviews)
"The staff is so welcoming and helpful. The towels and linens are spotless clean, and that’s a big deal to me . Thanks for the great stay"

Reviewed on 10 July 2026

Kompose Boutique Hotel
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is NZ$379 per night from 28 July to 29 July
NZ$379
28 July - 29 July
includes taxes & fees
9.2/10 Wonderful! (2,974 reviews)
"Espectacular lo recomiendo al maximoo lo vuelvo a repetir que n cuanto pueda"

Reviewed on 11 July 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
The price is NZ$381 per night from 10 Aug to 11 Aug
NZ$381
10 Aug - 11 Aug
includes taxes & fees
9.4/10 Exceptional! (2,353 reviews)
"This is our second time at Compass Margaritaville at Anna Maria Island, and our whole family is eager to return. The service is impeccable, and the breakfast is varied and hot. The location is ideal; you only have to drive a few minutes to reach the sand. We hope to return very soon."

Reviewed on 11 July 2026

Compass Hotel by Margaritaville Anna Maria Sound
See all 47,141 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.

Stay near popular Southwest Florida attractions

A lifeguard tower with an American flag, a green flag, and a signboard on a beach with people sunbathing and umbrellas.

Siesta Key Beach

9.6/10 (4,113 reviews)
Siesta Beach captivates with its unique quartz sand that stays cool even on hot days. Sink your toes into the powdery white shoreline while gazing at the clear turquoise waters that make this beach a favourite.
See properties

What to do in Southwest Florida

Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

NZ$108
per adult
100% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Scenic Sunset Cruise in West Palm Beach

Scenic Hakuna Matata Sunset Cruise in West Palm Beach

NZ$117
per adult
94% of travellers recommend
Scenic Hakuna Matata Sunset Cruise in West Palm Beach
Cruise the Palm Beach Intracoastal on a 90 minute Tour

Cruise the Palm Beach Intracoastal on a 90 minute Tour

NZ$115
per adult
Cruise the Palm Beach Intracoastal on a 90 minute Tour
See all activities in Southwest Florida

Frequently asked questions

How much does a Southwest Florida holiday package cost?
Less than you might think — from just , in fact! By bundling flights, hotels and car rentals into your own custom-built holiday 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 holiday 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 travellers.
How far in advance should I book my Southwest Florida holiday?
Get rewarded with the widest variety at the cheapest prices by booking your holiday 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 holiday!
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 holiday 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 holiday is only a couple of clicks away.
Can I choose my airline with a Southwest Florida Expedia holiday 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 holiday 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 holiday 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.

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