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.

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A coastal cityscape with high-rise buildings, palm trees, and a clear blue sky.

South End

If you're spending some time in South End, South Marco Beach and Marco Island Ski & Watersports are top sights worth seeing.

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A sandy beach path with people walking, a wooden fence, and a clear blue sky with clouds.

Lido Key

Traverse a winding woodland path and spend the afternoon on this island’s secluded beaches before ending at a beachside bar to enjoy a spectacular sunset.

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A person carrying a child on their shoulders on a bridge with a view of greenery and a clear sky.

Central Naples

While visiting Central Naples, you might make a stop by sights like Naples Zoo at Caribbean Gardens and Naples Grande Golf Club.

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A vibrant building with a purple facade, a sign reading "Siesta," and a staircase leading to the entrance.

Siesta Key Village

Siesta Key Village is known for its stunning beaches, and with sights like Siesta Key Beach and Siesta Key Farmers Market, you won't get bored spending a day wandering around this part of Siesta Key.

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Southwest Florida Holiday

Our pick of the best Southwest Florida Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
NZ$111
14 Sept - 15 Sept
includes taxes & fees
9.2/10 Wonderful! (5,991 reviews)
"The room was clean I never saw any dirt or hair or anything to show other people have used it! 10/10"

Reviewed on 10 Sept 2026

Kompose Boutique Hotel
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
NZ$293
20 Sept - 21 Sept
includes taxes & fees
9.4/10 Exceptional! (2,556 reviews)
"Will definitely come back!"

Reviewed on 10 Sept 2026

Compass Hotel by Margaritaville Anna Maria Sound
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

560 S Collier Blvd Marco Island FL
Fully refundableReserve now, pay when you stay
NZ$466
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (2,020 reviews)
"Enjoyed the pool area also great access to the Gulf beach front.. having chairs and an umbrella is a plus. Well staffed. Only complaint, there were only 2 towels in the room which was quickly taken care of and the bathroom outlet kept tripping when trying to use hairdryer."

Reviewed on 9 Sept 2026

Hilton Marco Island Beach Resort and Spa
See all 47,357 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.
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A beach with lifeguard towers, clear turquoise water, and people sunbathing.

Lido Beach

9.4/10 (6,329 reviews)
Lido Beach enchants with pristine white sands and calm waters along Sarasota's coast. Spend the day swimming in crystal-clear waters before strolling to nearby St. Armands Circle for upscale dining.
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A statue in a plaza with palm trees, a building with a red-tiled roof, and a white building with a green awning.

St. Armands Circle

9.4/10 (5,556 reviews)
This elegant open-air marketplace blends upscale shopping with European charm, surrounded by historic Ringling statues. Browse over 130 boutiques and dine al fresco at pavement cafés overlooking Circle Park.
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Two people sitting on blue beach chairs facing the ocean.

Venice Beach

9.2/10 (2,687 reviews)
Known as the "Shark Tooth Capital of the World," Venice Beach offers pristine sands and clear Gulf waters. Search for fossilised treasures along the shoreline or simply relax beneath the iconic sail-style pavilion.
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A beach with white sand, turquoise water, and a rocky area in the foreground. There are palm trees and a building in the background.

Naples Beach

9.4/10 (6,040 reviews)
Pristine white sands and clear Gulf waters frame the historic Naples Pier, stretching 1,000 feet into the sea. Watch for dolphins while enjoying panoramic sunset views from this quintessential Florida beach.
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A bustling street with palm trees, a yellow building, and people walking.

Fifth Avenue South

9.4/10 (2,799 reviews)
Fifth Avenue South pulses as Naples' elegant heart, lined with upscale boutiques and art galleries. Stroll beneath swaying palms and enjoy ambient lighting and outdoor dining when the avenue truly comes alive.
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A beach with palm trees, a clear blue sky, and a building complex in the background.

Vanderbilt Beach

9.2/10 (2,388 reviews)
Vanderbilt Beach dazzles with powdery white sand and crystal-clear Gulf waters perfect for shell collecting. Arrive before sunset to witness the sky's dramatic transformation.
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The Mall at the University Town Center with a modern building, palm trees, and a clear sky.

Mall at University Town Center

9.0/10 (2,156 reviews)
The Mall at UTC offers a premier shopping experience with over 140 stores from luxury boutiques to popular brands. Enjoy upscale dining options in a spacious, climate-controlled environment with modern architecture.
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What to do in Southwest Florida

Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

NZ$102
per adult
90% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Craft Beer and Wine Sunset Cruise in Palm Beach

Craft Beer and Wine Sunset Cruise in Palm Beach

NZ$99
per adult
100% of travellers recommend
Craft Beer and Wine Sunset Cruise in Palm Beach
Green sea turtle swimming by the snorkel trail

Guided Snorkel Tour Phil Foster Park (HIGH TIDE ONLY-FREE VIDEOS)

NZ$125
per adult
100% of travellers recommend
Guided Snorkel Tour Phil Foster Park (HIGH TIDE ONLY-FREE VIDEOS)
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.