Top Beach vacation packages in Southwest Florida

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

Pink Shell Beach Resort and Marina

$650

per person

Apr 27 - Apr 30

found 8 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.4/10 Exceptional! (1,159 reviews)

Clean room, great staff, great location. We will be back for sure!

Reviewed on Feb 18, 2026

Hilton Marco Island Beach Resort and Spa

South End

$883

per person

Mar 27 - Mar 29

found 10 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.8/10 Excellent! (1,645 reviews)

Beautiful room, comfortable beds. Wonderful amenities, Staff was very helpful! I’m definitely coming back!’

Reviewed on Feb 22, 2026

Sundial Beach Resort & Spa

Mid Island

$821

per person

Apr 27 - Apr 30

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.6/10 Excellent! (2,581 reviews)

Very clean room, staff was very nice. All of the pools were clean and everything was very nice and well taken care of.

Reviewed on Jan 30, 2026

Inn at Pelican Bay

Pelican Bay

$1,032

per person

Mar 27 - Mar 29

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Fort Myers (RSW)

9.6/10 Exceptional! (1,002 reviews)

Yes but I was not given the room we reserved deluxe king turned into deluxe twin. No vip recognition

Reviewed on Feb 19, 2026

JW Marriott Marco Island Beach Resort

South End

$1,364

per person

Mar 27 - Mar 29

found 10 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9/10 Wonderful! (1,000 reviews)

We love love love your resort service and. Beach !

Reviewed on Feb 22, 2026

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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

$821

per person

Apr 27 - Apr 30

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.6/10 Excellent! (2,581 reviews)

Very clean room, staff was very nice. All of the pools were clean and everything was very nice and well taken care of.

Reviewed on Jan 30, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

$2,765

per person

Apr 27 - May 1

found 12 hours ago

Roundtrip non-stop flight included

Grand Rapids (GRR) to Fort Myers (RSW)

6/10 (2 reviews)

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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

$650

per person

Apr 27 - Apr 30

found 8 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.4/10 Exceptional! (1,159 reviews)

Clean room, great staff, great location. We will be back for sure!

Reviewed on Feb 18, 2026

Naples Grande Beach Resort

Pelican Bay

Save 100% on your flight

$1,565

per person

Mar 27 - Mar 30

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9/10 Wonderful! (1,914 reviews)

Hotel rooms could use some updating. The lost a package and found it finally the last day of my stay. They were helpful in finding it but it was a frustrating experience.

Reviewed on Feb 24, 2026

Sundial Beach Resort & Spa

Mid Island

$821

per person

Apr 27 - Apr 30

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

8.6/10 Excellent! (2,581 reviews)

Very clean room, staff was very nice. All of the pools were clean and everything was very nice and well taken care of.

Reviewed on Jan 30, 2026

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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.

Lani Kai Beachfront Resort

Save 100% on your flight

$622

per person

Apr 27 - May 1

found 5 hours ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

8.8/10 Excellent! (1,009 reviews)

Staff was great inside the building, parking attendants were greatly unhelpful to customers of the hotel! Room was clean and mostly quiet! The atmosphere on th ground floor and the beach was very loud and extremely party oriented! Beware!

Reviewed on Feb 23, 2026

Tween Waters Island Resort & Spa

Save 100% on your flight

$718

per person

Apr 27 - May 1

found 10 hours ago

Roundtrip flight included

Chicago (CHI) to Fort Myers (RSW)

8.6/10 Excellent! (1,002 reviews)

Staff and location were good. Only complaint is that people were saving chairs at the pool but not using them. Folks would leave a towel or bag on the chair and be gone for hours.

Reviewed on Feb 21, 2026

Sanibel Inn

East End

Save 100% on your flight

$1,102

per person

Apr 27 - May 1

found 5 hours ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

9/10 Wonderful! (1,000 reviews)

Great staff, pool, view, food

Reviewed on Feb 15, 2026

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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 $622. 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

Margaritaville Beach Resort Fort Myers

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! (1,902 reviews)

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

Travelers say...

We had a fabulous stay! So many great amenities, restaurants, pool and beach area. The staff is so friendly and helpful. We’ll definitely return!

Reviewed on Feb 24, 2026

Marco Beach Ocean Suites

480 S Collier Blvd Marco Island FL

3 hours drive from Siesta Key Beach

At this resort, get ready to stroll along the shoreline in Marco Island, as you'll be close to South Marco Beach. Amenities at Marco Beach Ocean Suites include ...

8.8/10 Excellent! (1,230 reviews)

Travelers like: on the beach, beach towels

Travelers say...

Room was clean, and nice. Staff was courteous. We were especially impressed with the bartender at the "beach" bar (unfortunately did not get his name). We were aware that the pool was undergoing renovations, but we didn't realize the work/noise would start at 7am. Food and drink options in the hotel ...

Reviewed on Feb 24, 2026

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! (1,970 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

clean, was freezing out couldn’t go outside for any resort amenities, but had to pay for them but was a nice huge breakfast buffet

Reviewed on Feb 24, 2026

See all 46,626 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.