Florida Keys Beach Vacations
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Top Beach vacation packages in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Matecumbe
Save 100% on your flight
Price was $502, price is now $302 per person
$302
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (1,288 reviews)
Not a good experience. Dog poop on the pathway leading to the pool. We had room 319. Construction going on both sides of the hall between the elevator and the room. Ceiling torn out. Banging and hammering. We enjoyed staying here previously. We will never come back!!
Reviewed on Jul 10, 2026
La Siesta Resort & Villas
Matecumbe
Price was $735, price is now $524 per person
$524
per person
Aug 9 - Aug 12
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,007 reviews)
The room was very dirty when we arrived. The location and view from the room was amazing. The pool was great except it had black spots all over, which looked like black mold. There were also metal brush bristles from the staff cleaning the pool, on the bottom of the pool and a few people were cut while swimming. The pool attendant told us that the amenities were closed because of the wind being over 10 knots, including the Rum Runner, which wasn’t and shouldn’t have been the case. We later saw the rum runner dropping people off. We were very upset because we were looking forward to going on it one last time before the end of our trip. We lost a full day of using the paddle boards and kayaks and the Rum Runner. The staff was very friendly and accommodating when we talked to them about our issues.
Reviewed on Jul 9, 2026
Hawks Cay Resort
Price was $944, price is now $684 per person
$684
per person
Sep 10 - Sep 13
found 24 hours ago
Roundtrip non-stop flight included
Pensacola (PNS) to Miami (MIA)
8.2/10 Very Good! (1,006 reviews)
We have a second part of staying
The first part was NOT GOOD
Refrigerator broken
AC broken
They tried and corrected by moving to another room
11pm doing the whole work again
But we still here for another reservation done
Let’s see !!!
Reviewed on Jul 8, 2026
Pier House Resort & Spa
Key West Historic District
Price was $913, price is now $669 per person
$669
per person
Sep 9 - Sep 12
found 1 hour ago
Roundtrip non-stop flight included
Washington (IAD) to Key West (EYW)
9/10 Wonderful! (1,199 reviews)
From check in to check out very accommodating and friendly. The grounds were beautiful! Beach front was great for being in Key West! Room was comfortable and clean. Restaurants were great. Best side of the Island to be on. Everything was walkable. Right at the end of Duval. So many options around. Perfect spot!
Reviewed on Jul 8, 2026
Tranquility Bay Beachfront Hotel and Resort
Price was $650, price is now $491 per person
$491
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.8/10 Excellent! (1,004 reviews)
This is an outstanding set up for families with kids. I would definitely stay here again. The staff at check in was fair, housekeeping and around the pool excellent. I thought food and drinks on site were significantly overpriced. BYOB and plan to dine out in town.
Reviewed on Jul 10, 2026
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View all trips5* Beach vacations in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Cheeca Lodge & Spa
Matecumbe
Save 100% on your flight
Price was $440, price is now $354 per person
$354
per person
Aug 9 - Aug 12
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9.2/10 Wonderful! (1,330 reviews)
the place is great, is just need to be maintained a little better
Reviewed on Jul 10, 2026
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View all trips3 Night Beach vacations in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Amara Cay Resort
Matecumbe
Save 100% on your flight
Price was $502, price is now $302 per person
$302
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (1,288 reviews)
Not a good experience. Dog poop on the pathway leading to the pool. We had room 319. Construction going on both sides of the hall between the elevator and the room. Ceiling torn out. Banging and hammering. We enjoyed staying here previously. We will never come back!!
Reviewed on Jul 10, 2026
La Siesta Resort & Villas
Matecumbe
Price was $735, price is now $524 per person
$524
per person
Aug 9 - Aug 12
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,007 reviews)
The room was very dirty when we arrived. The location and view from the room was amazing. The pool was great except it had black spots all over, which looked like black mold. There were also metal brush bristles from the staff cleaning the pool, on the bottom of the pool and a few people were cut while swimming. The pool attendant told us that the amenities were closed because of the wind being over 10 knots, including the Rum Runner, which wasn’t and shouldn’t have been the case. We later saw the rum runner dropping people off. We were very upset because we were looking forward to going on it one last time before the end of our trip. We lost a full day of using the paddle boards and kayaks and the Rum Runner. The staff was very friendly and accommodating when we talked to them about our issues.
Reviewed on Jul 9, 2026
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $610, price is now $437 per person
$437
per person
Aug 9 - Aug 12
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
9/10 Wonderful! (1,199 reviews)
From check in to check out very accommodating and friendly. The grounds were beautiful! Beach front was great for being in Key West! Room was comfortable and clean. Restaurants were great. Best side of the Island to be on. Everything was walkable. Right at the end of Duval. So many options around. Perfect spot!
Reviewed on Jul 8, 2026
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See all available trips from Columbus to Florida Keys
View all trips4 Night Beach vacations in Florida Keys
Price found within the past 48 hours. Click for updated prices.
Drop Anchor
Save 100% on your flight
Price was $671, price is now $478 per person
$478
per person
Sep 10 - Sep 14
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Miami (MIA)
8.8/10 Excellent! (1,005 reviews)
The entry doors locks make me nervous very outdated. Also, requesting room service should be easier. Finally, I called the number I was given six times and never got a response even when I was calling, because of illegal activity on the property. Housekeeper was very nice and rooms were very clean.
Reviewed on Jul 8, 2026
Amara Cay Resort
Matecumbe
Save 100% on your flight
Price was $1,212, price is now $801 per person
$801
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.8/10 Excellent! (1,288 reviews)
Not a good experience. Dog poop on the pathway leading to the pool. We had room 319. Construction going on both sides of the hall between the elevator and the room. Ceiling torn out. Banging and hammering. We enjoyed staying here previously. We will never come back!!
Reviewed on Jul 10, 2026
Ibis Bay Beach Resort
Northside Resort
Price was $1,009, price is now $707 per person
$707
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Key West (EYW)
8.2/10 Very Good! (2,289 reviews)
Great property and excellent value. The place was clean and very nice. Really appreciated how clean and well kept everything was.
Reviewed on Jul 9, 2026
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View all tripsFind your perfect Florida Keys beach vacation
How do I book the best Florida Keys beach vacation packages?
Life’s a beach when you dive into our brilliant Florida Keys 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 Florida Keys?
A rental steps from the shore creates an amazingly affordable Florida Keys beach vacation. Seaside sojourns during low season start from $302. Prices and availability are subject to change. Additional terms may apply.
When should I book a Florida Keys 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 Florida Keys?
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 Florida Keys 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 Florida Keys 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 Florida Keys beach vacation deals?
Sort your search results by deals to delight in amazing Florida Keys 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 Florida Keys beach trip with free cancellation and/or flexible dates?
Just like the Florida Keys 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 Florida Keys 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 Florida Keys. (OK, maybe not that last part.)
Top Beach Florida Keys Hotels
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
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 ...
8.6/10 Excellent! (2,337 reviews)
Travelers like: on the beach, sun loungers, beach towels, outdoor pool
Travelers say...
"Elevator was down. All of them. My dad is handicap and their only solution was to give him “waived parking fee”. Not really a solution… in the meantime, I’m Hauling everything up 4 flights of stairs. They should’ve waived the parking fee for everyone. We’ve stayed here before. And came back an again. ..."
Reviewed on Jul 10, 2026
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
This spa hotel is a few steps from South Beach, where you can watch the sunset on your beach trip. Amenities at Southernmost Beach Resort and Guesthouses include ...
8.8/10 Excellent! (3,439 reviews)
Travelers like: on the beach, sun loungers, beach bars, beach yoga
Travelers say...
"found dirty ice bucket in room and every night the ceiling fan and light would come on and stay on or flash on and off. Told the office staff two days in a row and they only wanted to give me resort credit. Not concerned at all that our nights were disrupted at midnight every night! Seems by reading ..."
Reviewed on Jul 9, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard Key West FL
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 ...
8.8/10 Excellent! (1,821 reviews)
Travelers like: close to beach, outdoor pool
Travelers say...
"Exceptional hospitality. Food was excellent. Great location, would definitely recommend and also stay here again!"
Reviewed on Jul 10, 2026
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.
Things to do
Shark and Wildlife Viewing Adventure in Key West
$93
per adult
100% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
96% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
