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.

Inn at Pelican Bay

Pelican Bay

$749

per person

Dec 4 - Dec 7

found 5 hours ago

Roundtrip flight included

Atlanta (ATL) to Fort Myers (RSW)

9.6/10 Exceptional! (1,005 reviews)

Great breakfast, staff was very friendly and it was beautiful

Reviewed on Oct 4, 2026

Pink Shell Beach Resort and Marina

Save 100% on your flight

$1,868

per person

Dec 4 - Dec 9

found 20 hours ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

9.4/10 Exceptional! (1,454 reviews)

Sundial Beach Resort & Spa

Mid Island

$1,207

per person

Nov 3 - Nov 7

found 1 hour ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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

$1,366

per person

Nov 3 - Nov 5

found 7 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

Hilton Marco Island Beach Resort and Spa

South End

$1,032

per person

Dec 4 - Dec 9

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

9/10 Wonderful! (2,066 reviews)

Food a bit pricey.

Reviewed on Oct 4, 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

$1,207

per person

Nov 3 - Nov 7

found 1 hour ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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

$1,366

per person

Nov 3 - Nov 5

found 7 hours ago

Roundtrip flight included

Cleveland (CLE) 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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3 Night Beach vacations in Southwest Florida

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

Pink Shell Beach Resort and Marina

$644

per person

Dec 7 - Dec 10

found 14 hours ago

Roundtrip flight included

Cincinnati (CVG) to Fort Myers (RSW)

9.4/10 Exceptional! (1,454 reviews)

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,775

per person

Dec 23 - Dec 26

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Fort Myers (RSW)

9.6/10 Exceptional! (41 reviews)

Sundial Beach Resort & Spa

Mid Island

Save 100% on your flight

$730

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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

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

$670

per person

Dec 10 - Dec 14

found 6 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

7.4/10 Good! (1,000 reviews)

Edison Beach House

$671

per person

Dec 9 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (1,917 reviews)

Beautiful view!

Reviewed on Oct 3, 2026

Sundial Beach Resort & Spa

Mid Island

Save 100% on your flight

$946

per person

Dec 7 - Dec 11

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) 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

Don't see what you're looking for?

See all available trips from Columbus to Southwest Florida

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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 $644. 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 ...

9.4/10 Exceptional! (2,597 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"First things first: Nya was amazing. Excellent customer service. For the most part the hotel was clean and pleasant. As someone who is allergic to dogs, traveling these days is hard but we made a note prior to arrival and our room was very clean and quiet. That said, I was really disappointed that ..."

Reviewed on Oct 4, 2026

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 ...

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.