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Vacation rentals in Florida Keys

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Popular amenities for Florida Keys vacation rentals

Houses in Florida Keys

Guest favorite
Home in Naples
5 out of 5 average rating, 7 reviews

House In Naples Park

JenniferRating, 5 stars1 month ago
Great place to stay when visiting Naples. The house is just as it is described and looks just like the pictures. Very clean and well kept. Spiro is a great host. Let us check in early and communication with him is very quick and he is helpful with any problems. We will definitely stay here again.
Guest favorite
Home in Coral Gables
4.93 out of 5 average rating, 137 reviews

Beautiful house in Miami 5 minute away / airport .

MannyRating, 5 stars6 days ago
Amazing place! I was extremely clean and perfect! Definitely a place to repeat! Thanks
Guest favorite
Home in Hollywood
4.92 out of 5 average rating, 160 reviews

Hard Rock Villa - House With Pool & Selfie Walls

CorneliusRating, 5 stars1 week ago
My daughter and I fell in love with the house. More than enough room for my family and I. The pool was a plus kids enjoyed it.. Any questions I had for the host was answered in a timely manner.. Thank You Joseph for sharing your house with my family and I… ❤️
Guest favorite
Home in Miami
4.89 out of 5 average rating, 113 reviews

Beautiful Quiet Neighborhood

DairenysRating, 5 stars1 month ago
Enchanted with the accommodation a very nice and organized neighborhood,the house super cozy and comfortable. The very attentive hosts, Pablo always cared about ensuring a good stay would gladly return.
Guest favorite
Home in Fort Lauderdale
4.88 out of 5 average rating, 147 reviews

Tropical paradise 3/2 House near Beach heated pool

LouisRating, 5 stars2 weeks ago
Communication was great and everything in order. I would stay here again.
Top guest favorite
Home in Fort Lauderdale
4.75 out of 5 average rating, 12 reviews

Casa Sol -Hot tub-Private backyard-10 min to Beach

JoriRating, 5 stars1 month ago
Beautiful home in walking distance to restaurants and grocery store. Felt right at home. Super clean. Felt very safe walking around the area. We were only there one night, but would highly recommend.
Superhost
Home in Marco Island
4.54 out of 5 average rating, 13 reviews

Pet-friendly home w/ pool & steps to beach/food

RandyRating, 5 stars6 months ago
The house was great and we really enjoyed the back patio & pool. There were 4 of us (two couples) and we had plenty of space and were very comfortable. The kitchen & living room area was also very nice & well furnished. I would like to thank the owner for opening up there home & allowing us to have a wonderful stay in Marco Island.
Guest favorite
Home in Fort Lauderdale
4.91 out of 5 average rating, 103 reviews

Modern Beach House! 5BR/5BA + POOL!

RobbieRating, 5 stars2 months ago
Great place! A lot of space and great for group travel!

Private vacation rentals in Florida Keys

Top guest favorite
Home in Naples
5 out of 5 average rating, 14 reviews

Palm Tree Paradise - 1 Mile To The Beach

RichRating, 5 stars5 months ago
Danielle was very proactive and communitive. She reached out to us several times to confirm that everything was ok. The house was everything we expected and the location was awesome!!
Superhost
Villa in North Bay Village
4.81 out of 5 average rating, 43 reviews

1Bd 1Bth Private Island Security Gated Villa Miami

AlexeyRating, 5 stars66 months ago
The villa is in save quite place. Nice to be inside. Short drive to Miami Beach. Hans met us in person and showed everything. Definitely recommend place to stay.
Superhost
Home in Naples
4.92 out of 5 average rating, 12 reviews

Naples Retreat: Salt Pool & Spa, Prime Location

CarlosRating, 5 stars2 weeks ago
Everything was great and the house was very nice. We stayed only for one night and we found everything was easy, and fast to setup. Thanks for everything!
Top guest favorite
Home in Wilton Manors
5 out of 5 average rating, 102 reviews

Private & Cabana Heated Pool in Wilton Manors

VinnieRating, 5 stars4 months ago
We loved the space! Ralph and Frank were fantastic hosts! They were responsive, friendly and very accommodating! The whole place is wonderful, but the pool area is heaven! It is your own personal space and very relaxing. I highly recommend this place!
Guest favorite
Home in Marathon
4.89 out of 5 average rating, 73 reviews

Dream Vacation KCB Marathon with private pool !

LisaRating, 5 stars1 month ago
Alfonso is a very responsive host who provided clear details, local recommendations (multiple of which we used), and provided a place in a great location. Neighbors are friendly. Place was clean. Perfect for our family with a 14 and 6 year old.
Superhost
Home in Fort Lauderdale
4.83 out of 5 average rating, 160 reviews

Large Waterfront House with Pool 4bd/2ba

JaclynRating, 5 stars3 weeks ago
Everything was amazing Hosts were amazing. They truly accommodated us with our early arrival. This house was absolutely immaculate. When you walk in, you can actually smell how clean the entire house is. I saw reviews that others had issues with the construction going on. We had no issues with noise. If you are outside on the pool having a good time, you don’t even know they are there and the house is pretty much sound proof, so you do not hear them while you are inside. I would definitely want to go back. Thank you both for your amazing house
Guest favorite
Casa particular in Naples
5 out of 5 average rating, 6 reviews

Chic-Kee Bungalow 2

CindyRating, 5 stars2 months ago
If I could give Caitlin’s place 10 stars I would! It was exactly as described and better. It was beautifully decorated and had many little touches that made it seem like home. Everything was exceptionally clean and neat. She had everything we needed for our stay and everything was very organized. The location was perfect and close to everything we wanted to do. It felt completely private even though we shared a building with another guest…you didn’t even know anyone else was there. The guests we did meet walking in and out were very friendly. The backyard and grounds were like an oasis, …beautifully landscaped. Being pet friendly was wonderful too. I highly recommend this cottage! It’s perfect for a couple to spend a few days or a few months in Naples!
Superhost
Villa in Fort Lauderdale
5 out of 5 average rating, 4 reviews

Large 3 bedroom heated pool large Yard

HennyRating, 5 stars2 months ago
We just finished our stay at this location. This place is awesome. The pool and hot tub were clean and heated. We wanted the pool a bit warmer all it took was a call to Ron and within minutes the temp was up. We never yet had a host to be so available regardless of how many times you call or message him. We had an issue with our scheduling and Ron was very understanding and accommodative. It's a great place and a must see! Thanks Ron, we appreciate all you did.

Family friendly vacation rentals in Florida Keys

Guest favorite
Villa in Fort Lauderdale
4.94 out of 5 average rating, 265 reviews

Tropical Bungalow w/ Pool Tiki Hut and Full Gym

KatieRating, 5 stars3 weeks ago
My family and I had a great time! The pool and outdoor space is absolutely beautiful. The inside is open and spacious and great for a family. I would definitely stay here again and would recommend staying here to others!
Guest favorite
Home in Key West
4.92 out of 5 average rating, 283 reviews

Family House, 2 K BR's, Private Spa/Deck, 2 pools.

StedmanRating, 5 stars1 week ago
We loved our stay and will definitely recommend to friends and family. Hope to return someday soon!
Superhost
Townhouse in Key West
4.93 out of 5 average rating, 219 reviews

Spotlessly clean 3 bedroom/3 bathroom family home

GeorgiaRating, 5 stars3 weeks ago
This was a cute little place in a gated complex. It was well decorated to feel like a Key West getaway and a great place for sibs get-together. We liked the quiet, but be aware you will need to drive to get to Key West.
Guest favorite
Home in Naples
4.94 out of 5 average rating, 228 reviews

Cathedral Heights

KatherineRating, 5 stars1 week ago
A group of four of us stayed for 3 days so that we could attend a friend's memorial service in Seagate and had an absolutely wonderful experience at Christopher's home. The home was extremely clean, had very comfortable beds, lovely bed linens and plush towels and absolutely beautiful dishware, glassware and cookware. If you happen to forget something, it is in the home! They included all kinds of toiletries (shampoo, conditioner, soap, hairdryers, curling irons, makeup remover etc. The pool was spectacular and the backyard was extremely private. In addition, the landscaping is gorgeous and the neighborhood itself is quite lovely. We felt extremely safe there. I had to work briefly (remotely) while staying at Christopher's home and the upstairs loft was the perfect space for me as it had a desk/work station and the WIFI is extremely fast. The home is close to fantastic restaurants and shopping as well. If you need to stay in Naples, STAY HERE - you won't regret it.
Guest favorite
Apartment in Fort Lauderdale
4.79 out of 5 average rating, 301 reviews

Minute from the beach # 2

TakiaRating, 5 stars1 month ago
I enjoyed our stay! Great host that went above and beyond to meet our accommodations. Close walk to beach and local shops. The unit was also very clean and was exactly what I expected.
Top guest favorite
Condo in Key West
5 out of 5 average rating, 24 reviews

EYW Getaway

RootwaRating, 5 stars2 weeks ago
Edward's place was great! we really enjoyed the home like vibe. It had everything we needed during the stay. The sunset view from the balcony was beautiful.
Superhost
Home in Naples
4.82 out of 5 average rating, 166 reviews

Coastal Getaway w/ Inground Heated Pool

AngieRating, 5 stars3 months ago
Girls trip to Naples for a long weekend. This house felt comfortable and we enjoyed their beautiful house. Vanderbilt beach is so close and some great restaurants near by. I would highly recommend this house.
Superhost
Condo in Tavernier
4.76 out of 5 average rating, 365 reviews

Florida Keys Getaway - Slps 4 - Ocean View

NickRating, 5 stars3 weeks ago
Melanie was awesome and accommodating with our questions and needs. So much to do on the property for couples and families. We loved the pool, beach front and pickleball available all on site. We will definitely be back again!

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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