Southwest Florida Beach Vacations 2026

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Top Beach vacation packages in Southwest Florida

Price found within the past 48 hours. Click for updated prices.

Pink Shell Beach Resort and Marina

$600

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.4/10 Exceptional! (1,454 reviews)

Sundial Beach Resort & Spa

Mid Island

$786

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.6/10 Excellent! (2,700 reviews)

Tiki bar and restaurants were excellent and very good prices for excellent food. All staff were so helpful. So much to do. Rooms were spacious and comfy

Reviewed on Oct 1, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,368

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

Inn at Pelican Bay

Pelican Bay

$967

per person

Dec 15 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Oakland (OAK) to Fort Myers (RSW)

9.6/10 Exceptional! (1,005 reviews)

Lovely place to stay. Great room

Reviewed on Oct 5, 2026

Hilton Marco Island Beach Resort and Spa

South End

$946

per person

Dec 9 - Dec 13

found 13 hours ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9/10 Wonderful! (2,075 reviews)

Room was nice, clean and smelled good, pool was big and having the beach in the back was the best by far.

Reviewed on Oct 6, 2026

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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

Mid Island

$786

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.6/10 Excellent! (2,700 reviews)

Tiki bar and restaurants were excellent and very good prices for excellent food. All staff were so helpful. So much to do. Rooms were spacious and comfy

Reviewed on Oct 1, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,368

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

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.

Pink Shell Beach Resort and Marina

$600

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.4/10 Exceptional! (1,454 reviews)

Sundial Beach Resort & Spa

Mid Island

$786

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.6/10 Excellent! (2,700 reviews)

Tiki bar and restaurants were excellent and very good prices for excellent food. All staff were so helpful. So much to do. Rooms were spacious and comfy

Reviewed on Oct 1, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,467

per person

Dec 12 - Dec 15

found 13 hours ago

Roundtrip flight included

Washington (WAS) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

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4 Night Beach vacations in Southwest Florida

Price found within the past 48 hours. Click for updated prices.

Lido Islander Inn

$491

per person

Nov 7 - Nov 11

found 9 hours ago

Roundtrip flight included

Cincinnati (CVG) to Tampa (TPA)

7.4/10 Good! (1,000 reviews)

The Lighthouse Resort Inn & Suites

Save 100% on your flight

$827

per person

Nov 7 - Nov 11

found 10 hours ago

Roundtrip non-stop flight included

Bangor (BGR) to Fort Myers (RSW)

8.6/10 Excellent! (1,800 reviews)

Tween Waters Island Resort & Spa

Save 100% on your flight

$741

per person

Dec 9 - Dec 13

found 20 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,003 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

View all trips

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 $491. 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

Compass Hotel by Margaritaville Anna Maria Sound

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 ...

Hyatt Vacation Club at Coconut Cove, Bonita Springs

11800 Coconut Cove Drive Bonita Springs FL

2 hours drive from Siesta Key Beach

Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs ...

9.2/10 Wonderful! (1,008 reviews)

"This was an amazing place to stay. The staff was amazing. The rooms were clean and the amenities were great. we will definitely be returning."

Reviewed on Oct 6, 2026

Marriott Sanibel Harbour Resort & Spa

17260 Harbour Pointe Dr Fort Myers FL

2 hours drive from Siesta Key Beach

Stroll along the shore in Fort Myers, as you'll be a short walk from Sanibel Harbour Beach when booking a getaway at this spa resort. 3 outdoor pools, 5 outdoor ...

See all 47,652 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.