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

$747

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

9.6/10 Exceptional! (1,004 reviews)

Such a beautiful boutique inn. My boyfriend and I enjoyed being here. We had a gorgeous lake view king room. Highly recommend.

Reviewed on Sep 12, 2026

Sundial Beach Resort & Spa

Mid Island

$1,000

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

We booked with a 3rd party , the web pics showed a balcony. Are room had now balcony. Went to Terry Manager was accommodating although he stated the pics from a 3rd party was on 3rd party web not on the resorts web. Needless to say every was very clean the tiki bar staff very sweet. Be warned iof the sand flees u can not see them and they will eat u alive

Reviewed on Sep 12, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$4,601

per person

Nov 12 - Nov 15

found 15 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

Outstanding massage

Reviewed on Sep 1, 2026

Pink Shell Beach Resort and Marina

$777

per person

Oct 12 - Oct 15

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.4/10 Exceptional! (1,447 reviews)

Hilton Marco Island Beach Resort and Spa

South End

$971

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

9/10 Wonderful! (2,004 reviews)

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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

$1,000

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Reviewed on Sep 12, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$4,601

per person

Nov 12 - Nov 15

found 15 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

Outstanding massage

Reviewed on Sep 1, 2026

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.

Inn at Pelican Bay

Pelican Bay

$747

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Fort Myers (RSW)

9.6/10 Exceptional! (1,004 reviews)

Such a beautiful boutique inn. My boyfriend and I enjoyed being here. We had a gorgeous lake view king room. Highly recommend.

Reviewed on Sep 12, 2026

Sundial Beach Resort & Spa

Mid Island

$1,000

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Reviewed on Sep 12, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$4,601

per person

Nov 12 - Nov 15

found 15 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

Outstanding massage

Reviewed on Sep 1, 2026

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.

The Lighthouse Resort Inn & Suites

$547

per person

Nov 12 - Nov 16

found 22 hours ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

8.6/10 Excellent! (1,787 reviews)

Very nice hotel especially for the price, front desk actually checks in on you through out stay …will go again

Reviewed on Sep 12, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$731

per person

Nov 12 - Nov 16

found 1 hour ago

Roundtrip flight included

Minneapolis (MSP) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Edison Beach House

$796

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip flight included

Appleton (ATW) to Fort Myers (RSW)

9.4/10 Exceptional! (1,888 reviews)

😊😊😊😊

Reviewed on Sep 9, 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 $547. 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 Bonita Springs Public Beach and Hertz ...

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 47,403 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.