Top Beach vacation packages in Key West

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

per person

Sep 17 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Key West (EYW)

8.6/10 Excellent! (2,662 reviews)

Food and drinks are expensive but good. Not much in terms of entertainment at the resort but there are multiple pools to explore.

Reviewed on Aug 17, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

per person

Oct 18 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Key West (EYW)

8.4/10 Very Good! (269 reviews)

Beautiful and clean facility. Customer service is excellent

Reviewed on Aug 17, 2025

La Concha Key West, Autograph Collection

Key West Historic District

per person

Oct 19 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Key West (EYW)

9/10 Wonderful! (184 reviews)

Walking distance from everything

Reviewed on Aug 11, 2025

Southernmost House

Old Town Key West

per person

Oct 18 - Oct 21

found 14 hours ago

Roundtrip non-stop flight included

Dallas (DAL) to Key West (EYW)

9.4/10 Exceptional! (1,004 reviews)

This hotel is beautiful, love the history Bed comfortable Would definitely come and stay here again

Reviewed on Aug 15, 2025

Pier House Resort & Spa

Key West Historic District

per person

Sep 17 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Key West (EYW)

9/10 Wonderful! (1,014 reviews)

We live Pier House. Have stayed before. Unfortunately we were stuck in a "Junior Spa Suite" in rear spa building this time. Our "patio" was in the rear parking lot. Literally. Loud at night and in am with cars, workers. Patio walls rusted . Room small amd cramped. Will say it was very clean . Mattress a bit hard . Fees upon fees upon fees added plus ridiculous drink prices . Was not worth what I paid ...should have had an oceanfront suite for what I paid instead had ghetto suite

Reviewed on Aug 17, 2025

Don't see what you're looking for?

See all available trips from Columbus to Key West

View all trips

3 Night Beach vacations in Key West

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

Southernmost Beach Resort and Guesthouses

Old Town Key West

per person

Sep 17 - Sep 20

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Key West (EYW)

8.6/10 Excellent! (2,662 reviews)

Food and drinks are expensive but good. Not much in terms of entertainment at the resort but there are multiple pools to explore.

Reviewed on Aug 17, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

per person

Oct 18 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Key West (EYW)

8.4/10 Very Good! (269 reviews)

Beautiful and clean facility. Customer service is excellent

Reviewed on Aug 17, 2025

La Concha Key West, Autograph Collection

Key West Historic District

per person

Oct 19 - Oct 22

found 4 hours ago

Roundtrip flight included

Atlanta (ATL) to Key West (EYW)

9/10 Wonderful! (184 reviews)

Walking distance from everything

Reviewed on Aug 11, 2025

Don't see what you're looking for?

See all available trips from Columbus to Key West

View all trips

4 Night Beach vacations in Key West

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

Ibis Bay Beach Resort

Northside Resort

Save 100% on your flight

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip flight included

Allentown (ABE) to Key West (EYW)

8.2/10 Very Good! (2,009 reviews)

The room was quite small and the bathroom was very small where there was hardly space to leave items such as toothbrushes etc. The shower is so tight that one can barely fit in it. The entrance to the room is tight where cars are parked too close to the room door. No microwave included in the room so one cannot warm up any leftovers or warmup any water to make any tea in the night. Breakfast was good that included ham, cheese, boiled eggs, bread, waffles, yogurt, coffee and tea.

Reviewed on Aug 16, 2025

Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Save 100% on your flight

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip flight included

Allentown (ABE) to Key West (EYW)

9/10 Wonderful! (768 reviews)

Room was tight but more importantly dirty. The floor in the bathroom was grimy and the shower moldy.

Reviewed on Aug 13, 2025

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Save 100% on your flight

per person

Oct 18 - Oct 22

found 1 day ago

Roundtrip flight included

Allentown (ABE) to Key West (EYW)

8.4/10 Very Good! (269 reviews)

Beautiful and clean facility. Customer service is excellent

Reviewed on Aug 17, 2025

Don't see what you're looking for?

See all available trips from Columbus to Key West

View all trips

How do I book the best Key West beach vacation packages?

Life’s a beach when you dive into our brilliant Key West 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 Key West?

A rental steps from the shore creates an amazingly affordable Key West beach vacation. Seaside sojourns during low season start from $616. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Key West?

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 Key West 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 Key West 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 Key West beach vacation deals?

Sort your search results by deals to delight in amazing Key West 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 Key West beach trip with free cancellation and/or flexible dates?

Just like the Key West 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 Key West 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 Key West. (OK, maybe not that last part.)

Top Beach Key West Hotels

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

8 min drive from Duval Street

Make the most of this fantastic location, as you'll be close to a private beach with a stay at this hotel. 2 restaurants, 2 bars, and an outdoor pool are just ...

8.4/10 Very Good! (1,465 reviews)

Travelers like: on the beach, sun loungers, beach towels, outdoor pool

Travelers say...

"Food options was great, the bed comfort was a little to firm, but the linens was awesome, the suite was very equipped and beautifully updated. Did not get in the pool because the water was not circulating clean and maintenance at night, very nice pool area, but felt the pool water was not clean."

Reviewed on Aug 17, 2025

Margaritaville Beach House Key West

2001 South Roosevelt Boulevard, Key West, FL

4 min drive from Duval Street

At this hotel, get ready to stroll along the shoreline in Key West, as you'll be close to Florida Keys Beaches. Amenities at Margaritaville Beach House Key West ...

8.6/10 Excellent! (1,763 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"Our second time there! They actually saved our whole trip! We checked in at casa marina resort and immediately asked Expedia to relocate us to margaritaville beach house. This place is beautiful, beautiful landscape, beautiful clean rooms. The staff is so friendly, the pool is nice too even with ..."

Reviewed on Aug 16, 2025

Hyatt Vacation Club at Windward Pointe, Key West

3675 South Roosevelt Boulevard, Key West, FL

7 min drive from Duval Street

Recharge at this hotel and watch the sunset on the beach in Key West, as you'll be not far from the beach. An outdoor pool, a restaurant, and a hot tub are just ...

9.4/10 Exceptional! (1,005 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...

"Very comfortable accommodations and bedding was comfortable as well. The pool was nice and the drinks from the outdoor concession were great."

Reviewed on Aug 16, 2025

See all 2,720 properties in Key West

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.