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

South End

$480

per person

May 9 - May 11

found 1 day ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

9/10 Wonderful! (1,714 reviews)

Ocean view, great room

Reviewed on Mar 6, 2026

Inn at Pelican Bay

Pelican Bay

$490

per person

May 10 - May 12

found 5 hours ago

Roundtrip flight included

Philadelphia (PHL) to Fort Myers (RSW)

9.6/10 Exceptional! (1,001 reviews)

Friendly, well organized, large rooms.

Reviewed on Mar 3, 2026

Sundial Beach Resort & Spa

Mid Island

$602

per person

May 10 - May 12

found 5 hours ago

Roundtrip flight included

Philadelphia (PHL) to Fort Myers (RSW)

8.6/10 Excellent! (2,603 reviews)

The room was good condition, we enjoyed the pickleball courts. The food was pricey and just so so quality.

Reviewed on Mar 1, 2026

Pink Shell Beach Resort and Marina

$1,319

per person

Apr 10 - Apr 12

found 21 hours ago

Roundtrip flight included

Indianapolis (IND) to Fort Myers (RSW)

9.4/10 Exceptional! (1,276 reviews)

It was honestly the best vacation. First and foremost, the place and views are beautiful, the staff was so friendly, polite, and curious, they have everything right there, and the food and complimentary breakfast was exceptional. It was a perfect stay, at the pink shell resort!

Reviewed on Mar 8, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

$3,299

per person

Apr 8 - Apr 11

found 18 hours ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

8.8/10 Excellent! (3 reviews)

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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

$602

per person

May 10 - May 12

found 5 hours ago

Roundtrip flight included

Philadelphia (PHL) to Fort Myers (RSW)

8.6/10 Excellent! (2,603 reviews)

The room was good condition, we enjoyed the pickleball courts. The food was pricey and just so so quality.

Reviewed on Mar 1, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

$3,299

per person

Apr 8 - Apr 11

found 18 hours ago

Roundtrip flight included

New York (NYC) to Fort Myers (RSW)

8.8/10 Excellent! (3 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.

Hilton Marco Island Beach Resort and Spa

South End

$597

per person

May 12 - May 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,714 reviews)

Ocean view, great room

Reviewed on Mar 6, 2026

Pink Shell Beach Resort and Marina

$738

per person

May 11 - May 14

found 1 day ago

Roundtrip flight included

New York (JFK) to Fort Myers (RSW)

9.4/10 Exceptional! (1,276 reviews)

It was honestly the best vacation. First and foremost, the place and views are beautiful, the staff was so friendly, polite, and curious, they have everything right there, and the food and complimentary breakfast was exceptional. It was a perfect stay, at the pink shell resort!

Reviewed on Mar 8, 2026

Sundial Beach Resort & Spa

Mid Island

$1,494

per person

Apr 8 - Apr 11

found 22 hours ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

8.6/10 Excellent! (2,603 reviews)

The room was good condition, we enjoyed the pickleball courts. The food was pricey and just so so quality.

Reviewed on Mar 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.

Tropical Beach Resorts

South Village

Save 100% on your flight

$536

per person

May 18 - May 22

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Sarasota (SRQ)

9.4/10 Exceptional! (5,331 reviews)

Very clean and short walk to the beautiful beach

Reviewed on Mar 9, 2026

Hilton Marco Island Beach Resort and Spa

South End

Save 100% on your flight

$638

per person

May 10 - May 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9/10 Wonderful! (1,714 reviews)

Ocean view, great room

Reviewed on Mar 6, 2026

Tropical Breeze Resort

Siesta Key Village

Save 100% on your flight

$1,441

per person

Apr 8 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

Cincinnati (CVG) to Sarasota (SRQ)

9/10 Wonderful! (1,001 reviews)

The property is a block off the ocean, easy walk to the beach.

Reviewed on Mar 6, 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 $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

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

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! (1,929 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

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! (1,985 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

great pool

Reviewed on Mar 9, 2026

See all 46,843 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.