Vacation rentals in Florida Keys

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Popular amenities for Florida Keys vacation rentals

Houses in Florida Keys

Top guest favorite
Home in Marathon
4.99 out of 5 average rating, 136 reviews

Cancellation Deal: 07/26 thru 08/09

KevinRating, 5 stars6 days ago
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie
Top guest favorite
Home in Islamorada
4.97 out of 5 average rating, 192 reviews

Flakey's

EmmaRating, 5 stars1 month ago
Cheryl’s place is in the perfect location in the heart of Islamorada. Listening to the live music on the back deck to wind down every night was an added plus! Cheryl was super accommodating & definitely thinks about bettering her guests’ stay. Couldn’t recommend this place more!
Guest favorite
Home in Key Largo
4.97 out of 5 average rating, 106 reviews

The Paradise 2

LisaRating, 5 stars2 weeks ago
Our stay exceeded our expectations! Everything from the instructions for checkin and out from the host to the beautiful house and location was above and beyond. The houae is so perfect and you truly feel like you are in Paradise everyday! The sunrise and sunset are breathtaking from the deck/dock. ALL of the advertised pictures are exactly what to expect but even better in person. I enjoyed the pool as much as sitting on the deck and dock. Our son is 12 and a fisherman and he was able to fish from sun up to sundown! Our family will be returning hopefully several more times! Thank you Luis for sharing your piece of Paradise will our family!
Guest favorite
Home in Key Colony Beach
4.95 out of 5 average rating, 116 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

TinaRating, 5 stars6 days ago
We were very comfortable at the home during our week stay. Great place to stay if you need room to park a boat trailer. Quiet very nice safe neighborhood.
Top guest favorite
Home in Key Largo
4.99 out of 5 average rating, 181 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

AngelaRating, 5 stars1 week ago
An absolutely immaculate and very well equipped property in a stunning location overlooking the marina. Highlights were sitting on the terrace watching the glorious sunsets and standing on the jetty looking at the sharks and other fish swimming around (free fish food is supplied which attracts them!). The Backyard Cafe located at the Key Largo Fishery is a minute's walk away - it's very laid back and serves great fish dishes and drinks; there was also live music on the weekend. Thank you Ray, we loved your place and would happily have stayed forever!
Guest favorite
Home in Key West
4.95 out of 5 average rating, 339 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

ThomasRating, 5 stars2 weeks ago
This was a very nice place. Very quiet and peaceful! The location was perfect. This was our first time to the keys and we would highly recommend staying here!
Top guest favorite
Home in Key Colony Beach
4.96 out of 5 average rating, 105 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

BrandyRating, 5 stars3 weeks ago
We loved our stay! The host was very responsive and helpful with local recommendations. Great neighborhood and centrally located.
Guest favorite
Home in Marathon
4.96 out of 5 average rating, 114 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JasonRating, 5 stars1 week ago
We really enjoyed this home in Marathon. Sitting by the canal for morning coffee, swimming in the pool on a hot afternoon, having dinner on the covered porch, or plying corn hole on the roof… it was all super enjoyable. Andy even dropped off some wonderful bagels one morning! The location is super close to all that Marathon has to offer. We would recommend this home to anyone

Lake houses in Florida Keys

Superhost
Home in Homestead
4.88 out of 5 average rating, 184 reviews

Sukyia Charming House! Japanese Garden in SW Miami

MichaelRating, 5 stars2 weeks ago
Just the perfect place to stay, quite, comfortable, peaceful. I love staying here and plan on staying here again when I’m in town. My kids live 10 min away so it’s the perfect location for me. Ale was a great host. Responded quickly and friendly. Thank you
Superhost
Home in Key Largo
4.9 out of 5 average rating, 106 reviews

New Oceanside Casa Palma Voted #1! Golf Cart-Beach

JamiRating, 5 stars5 months ago
SUPER CLEAN & exactly as the picture show! Loved having the golf cart assessable and the grounds are spectacular! Nice swimming pool and fishing and Lagoon! My family had an excellent stay!
Guest favorite
Home in Pompano Beach
4.87 out of 5 average rating, 117 reviews

Heated Pool + Kayaks! Tiki Hut & Close To Beach!

JackieRating, 5 stars1 week ago
We had a blast at the house. The pool was lovely and all the surroundings - gardens, tiki bar etc were really beautiful. Lots of places to have space and privacy with our family. All the beach gear you would need as well. We especially loved being able to have a quick kayak around the canals. Thank you for a great stay!
Guest favorite
Home in Oakland Park
4.98 out of 5 average rating, 118 reviews

Waterfront Heated Pool,Jacuzzi, Pier, 2mi to Beach

KennethRating, 5 stars1 week ago
Carlos place was great. We had a good time in the pool and had a really good time fishing. it was peaceful and quiet and the home was really spacious. I would definitely rent his home again. Thanks Carlos for the enjoyable stay.
Superhost
Home in Key Largo
4.85 out of 5 average rating, 206 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

BrandonRating, 5 stars3 weeks ago
Fantastic stay. Bryant was an excellent host and very responsive and accommodating
Guest favorite
Home in Marco Island
4.89 out of 5 average rating, 174 reviews

"Waterfront & OceanAccess Oasis with Private Pool"

ChristineRating, 5 stars1 day ago
This was our first time visiting Marco Island. We had a wonderful time and enjoyed this home immensely. It was private, very clean, and was really close to beach and restaurants. We especially enjoyed the heated pool. We would definitely come back and would recommend this property to others interested in Marco Island.
Guest favorite
Home in Key Largo
4.91 out of 5 average rating, 107 reviews

Sunsets In Palms Paradise

TaylorRating, 5 stars3 weeks ago
We thoroughly enjoyed this house! The backyard is amazing with plenty of space to play cornhole, throw frisbees, and enjoy the beautiful weather. We saw a manatee behind the property and with the provided paddleboard got to see it close up as well! The house was clean and had all desired amenities . We will definitely be back.
Guest favorite
Home in Marco Island
4.86 out of 5 average rating, 103 reviews

HGTV’s “Vacation House for Free” Marco Island Home

LisaRating, 5 stars1 month ago
There’s a little slice of heaven on Earth, and it’s tucked away at 1432 Jamaica Road, Marco Island. I can't praise this home enough—though I fear that by doing so, I might just make it more popular and harder to book... but honestly, this house deserves to be shared with as many people as possible! It’s like being wrapped in a warm hug every time you step inside. It has everything you need, plus an extra dose of charm and coziness. Don’t hesitate to book this place. After staying at so many different homes over the years, this one stands out as our absolute favorite—thanks to its fantastic amenities, prime location, and the wonderful owners. It truly feels like home.

Family friendly vacation rentals in Florida Keys

Top guest favorite
Home in Marathon
4.94 out of 5 average rating, 187 reviews

May availability 70ft Dock, Near Beach VACA23-16

KristinRating, 5 stars1 month ago
Jeffrey’s place was a wonderful landing pad for our week in the keys. Lots of small details thought out that add up to a relaxing stay. (Beach towels, coolers and beach gear, family games, etc.) Kids didn’t wanted to live there forever!
Guest favorite
Home in Marathon
4.95 out of 5 average rating, 136 reviews

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

TashaRating, 5 stars6 days ago
Plenty of room for all the family and their families. We enjoyed all the backyard amenities with pool, kyacks, boat dockage and fish cleaning station. There was sufficient seating for everyone and a great area to hangout. The only things we struggled with was TVs didn’t work properly in some of the rooms, no washcloths or kitchen towels available. With that being said, we will definitely consider renting Ryan’s place again in the future!
Top guest favorite
Apartment in Key West
4.98 out of 5 average rating, 502 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

LeslieRating, 5 stars2 weeks ago
We had a really lovely stay at this space! It is as advertised and very clean. We used the kitchen every day and sometimes twice a day. What’s great about this space is that the patio and seating area is always in the shade…. at every hour of the day!
Top guest favorite
Villa in Marathon
4.95 out of 5 average rating, 138 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

IngridRating, 5 stars2 weeks ago
Our family of five adults, plus two additional relatives, had the most incredible stay at this property. While we had planned several excursions, we found ourselves spending the majority of our seven-day trip enjoying everything this place had to offer. From fishing off the dock to kayaking and paddleboarding, the outdoor amenities were top-notch. The pool area was the perfect spot for relaxing and spending quality time together. One of the standout features was the amazing outdoor freezer—ideal for storing our fresh catch of Mahi from our charter trip. Inside, the kitchen was impressively well-equipped, making cooking a breeze. Every detail of the home was thoughtfully curated to provide comfort and convenience. This stay exceeded our expectations, and we’re already looking forward to returning. Highly recommend for anyone seeking a well-appointed, adventure-filled getaway!
Top guest favorite
Home in Marco Island
4.98 out of 5 average rating, 308 reviews

⭐ Rare Waterfront Western Exposure Vacation Home

DavidRating, 5 stars1 week ago
Ed is a wonderful host. The house is lovely, on a lagoon with a private dock/lift for your boat. Short drive to restaurants and beaches or a healthy walk. Pool was very nice and bicycles, fishing poles, and other amenities were available for our convenience, and enjoyment. Would rent again and recommend Ed as a host.
Top guest favorite
Boat in Miami
4.98 out of 5 average rating, 796 reviews

Hunter 26 Sailboat

FreddyRating, 5 stars2 weeks ago
Perfect visit for me, the experience was just what I was looking for. The boat was comfortable, equipped with the essentials, and located in a quiet part of the marina with a nice walkable little island nearby. The kayaks are definitely a nice touch. Yaly was a very kind, accommodating, and a super responsive host. I look forward to going back in June and making it a regular activity on my schedule from now on. Thank you Yaly, see you again soon ;-)
Superhost
Condo in Tavernier
4.77 out of 5 average rating, 368 reviews

Florida Keys Getaway - Slps 4 - Ocean View

Angel MiguelRating, 5 stars2 weeks ago
Would come back again. Very peaceful and good location. Host was very responsive and friendly.
Superhost
Home in Key Colony Beach
4.91 out of 5 average rating, 140 reviews

Tiki Time 2

WarrenRating, 5 stars2 weeks ago
It was a great place inside and out. We had drinks under the tiki hut where it was cooled by the tropical breeze. Being on the ground floor, we seniors never had to climb stairs and the grounds were very even. The dock area was in fair shape but watch out for the small coconuts dropping from the palm trees. The laundry room was good and the machines were very clean and large capacity. The barbecue grill was ok, but the propane unit was rusty and the flames were very inconsistent. We enjoyed ourselves at the Cabana Club where the pool was great and the food there was the best for lunches and drinks

Your guide to Florida Keys

All About The Florida Keys

From vibrant Key West to the mysteriously named No Name Key, the Florida Keys offer historical intrigue and geographical wonder in a graceful archipelago, stretching out from the Everglades towards Havana. Postcard-worthy turquoise waters make the Keys a popular destination for sports fishing, scuba diving, and boating. If you fancy a more leisurely set of activities during your visit, boat rides in the tropical sun and snorkeling let you set your own pace for exploring the dazzling coral islands.

The strong culinary culture of the Keys is centered around fresh seafood, from mahi-mahi to snapper to blackfin tuna, alongside other edible delights, like Key lime pie on a stick. For those wanting to explore both land and sea, consider venturing into the Mel Fisher Maritime Heritage Museum or the Key West Shipwreck Treasure Museum, both of which are excellent forays into the impact the ocean has had on the history of these islands.


The best time to stay in a vacation rental in Florida Keys

The best time to look for Florida Keys vacation rentals is between March and May. There are typically fewer crowds during this time and the weather is still warm without being humid, unlike in the muggier summer months.. The islands also host a variety of events in the spring. The 7 Mile Bridge Run in April is an annual marathon spanning the entirety of one of the island’s bridges. The Taste of Key West, also in April, is an annual celebration of the various cuisines that call the archipelago home, and feature everything from fine dining to seafood shacks and food trucks. The Key West Songwriters’ Festival in May has been going strong for 25 years and features dozens of performers across genres such as country, reggae, and rock.


Top things to do in Florida Keys

Duval Street

Duval Street, running from Mallory Square to the Southernmost Point marker, is one of Key West’s most lively streets. Host to museums, shops, galleries, and cafes, Duval Street is great not only for people-watching, with its many annual parades and events, but also for learning about the history of the Florida Keys, with attractions such as the Ernest Hemingway Home and Museum, and the former Strand Theater.

Dry Tortugas National Park

Dry Tortugas National Park, 70 miles from Key West, is only accessible by boat or plane, but is a worthwhile stop on any trip to the Florida Keys. An archipelago of seven beach-ringed islands, one is taken up entirely by the preserved ruins of Fort Jefferson, which stands guard over the coral, seagrass, and shipwrecks that welcome snorkelers from around the world. Popular snorkeling spots are the Historic Coaling Pier, Fort Jefferson's moat wall, and Garden Key. Boaters can explore around Loggerhead Key's Little Africa Reef and the Windjammer Wreck.

Marathon

Not to be confused with the activity, or the location of the same name in Greece, Marathon is the sportfishing center of the Florida Keys. Charters are easily arranged here for deep-sea, reef, and flats fishing. A variety of beaches and beachfront restaurants line the strip, while the former Seven Mile Bridge on the island makes a scenic path for walkers, joggers, and cyclists.

Destinations to explore

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