Southwest Florida Beach Vacations

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Top Beach vacation packages in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Hilton Marco Island Beach Resort and Spa
Inn at Pelican Bay
Sundial Beach Resort & Spa
Pink Shell Beach Resort and Marina
Naples Beach Club, A Four Seasons Resort
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See all available trips from Columbus to Southwest Florida
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5* Beach vacations in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Sundial Beach Resort & Spa
Naples Beach Club, A Four Seasons Resort
Don't see what you're looking for?
See all available trips from Columbus to Southwest Florida
View all trips

3 Night Beach vacations in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Hilton Marco Island Beach Resort and Spa
Pink Shell Beach Resort and Marina
Sundial Beach Resort & Spa
Don't see what you're looking for?
See all available trips from Columbus to Southwest Florida
View all trips

4 Night Beach vacations in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Tropical Beach Resorts
Hilton Marco Island Beach Resort and Spa
Tropical Breeze Resort
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See all available trips from Columbus to Southwest Florida
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Find your perfect Southwest Florida beach vacation

How do I book the best Southwest Florida beach vacation packages?

Life’s a beach when you dive into our brilliant Southwest Florida beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Southwest Florida?

A rental steps from the shore creates an amazingly affordable Southwest Florida beach vacation. Seaside sojourns during low season start from $480. Prices and availability are subject to change. Additional terms may apply.

When should I book a Southwest Florida beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Southwest Florida?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Southwest Florida beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Southwest Florida vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Southwest Florida beach vacation deals?

Sort your search results by deals to delight in amazing Southwest Florida beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Southwest Florida beach trip with free cancellation and/or flexible dates?

Just like the Southwest Florida tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Southwest Florida beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Southwest Florida. (OK, maybe not that last part.)

Top Beach Southwest Florida Hotels

Azul Resort Siesta Key

Azul Resort Siesta Key

3 out of 5
1105 Point of Rocks Rd Siesta Key FL
  • 29 min walk from Siesta Key Beach
Watch the sunset on the beach in Siesta Key, as you'll be not far from Crescent Beach with a stay at this hotel. An outdoor pool, beach towels, and beach umbrellas ...
8.8/10 Excellent! (64 reviews)

Travelers like: on the beach, sun loungers, beach umbrellas, beach towels

Travelers say...
Sparkling clean room, bathroom, all pool areas!

Reviewed on Mar 8, 2026

Azul Resort Siesta Key
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
  • 2 hours drive from Siesta Key Beach
This spa hotel is the ideal choice for catching some rays on Crescent Beach Family Park if you're looking for a Fort Myers Beach vacation. Amenities at Margaritaville ...
9/10 Wonderful! (1,929 reviews)

Travelers like: on the beach, beach bars, outdoor pool

Travelers say...
Great resort, nice clean rooms, staff is very friendly and the pool and food are excellent.

Reviewed on Mar 8, 2026

Margaritaville Beach Resort Fort Myers
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
  • 41 min drive from Siesta Key Beach
Enjoy your stay at this hotel and get ready to stroll along the shoreline in Bradenton, as you'll be near the beach. An outdoor pool, a restaurant, and a 24-hour ...
9.4/10 Exceptional! (1,985 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...
great pool

Reviewed on Mar 9, 2026

Compass Hotel by Margaritaville Anna Maria Sound
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.

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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.