Florida Keys vacation rentals
Vacation rentals in Florida Keys by owner — compare homes, condos and cabins, message verified hosts and book direct. See every charge before you pay.
The Florida Keys are famed for their coral reefs around Key Largo, the historic streets of Old Town Key West, the Seven Mile Bridge, and the Dolphin Research Center in Marathon. Travelers indulge in scuba diving, snorkeling at John Pennekamp Coral Reef State Park, and exploring the Ernest Hemingway Home and Museum. Houfy connects you directly with local hosts throughout the Keys, offering rentals that help your budget stretch further. Find oceanfront villas, charming bungalows, and houseboats across the archipelago - all bookable direct. Most visitors head to the Keys from December to April when the weather is mild and dry.
Top-Rated Vacation Homes in Florida Keys
Browse the highest rated vacation properties in Florida Keys.
$4,432.46 USD total for 7 nights
Feb 27 – Mar 6, 2027
Stay Anchored is a wonderful vacation home in a great location! It’s a newer, modern property with a dock and a private pool in the backyard. The house is well maintained, clean, and fully stocked with lots of kitchen items, games, beach towels, and even an abundance of bath towels including make up towels. The bedding and linens are good quality along with the house furnishing. The house has a great floor plan on 2 floors so each bedroom has a bit of privacy. We had great communication with the owner. He sends out lots of great information and the rental agreement is easy to understand. He checked in with us after arrival and departure. We felt we could reach out to him at anytime for anything. He made us feel very welcome. We have stayed at an identical house a few houses down the road, and Stay Anchored is superior. We are looking forward to returning in the future. No more spending hours looking through rental sites. We have found the one that meets all of our needs and wants at a great value.
$1,897.50 USD $1,644.38 USD total for 6 nights
Oct 26 – Nov 1, 2026
We really had a lovely time and the apartment was exactly as described. The lounge area was very comfortable and it was all very well equipped. We were two lots of two so the apartment was perfect as there is a bathroom attached to each bedroom and gave each of us a lot of privacy. I would however seriously question how comfortable it would be for 8 people but for four it was fantastic The pool area was very pleasant and did not get too crowded and was spotlessly clean. There is not really any where that is an easy walk to eat or drink so you will need a car but there is plenty of safe private parking.There are no refreshments in the pool area but the apartment has cool boxes which were used frequently I think other posters make affair point about the pillows and it was a bit like lying on a crisp packet. I suspect most people did what we did and took the protective covers off which does defeat the object and I would suggest getting fabric covers instead. We heard no noise from neighbors and the layout seems generally to be very well designed. the location is close to the highway but no traffic noise and generally a very peaceful break. There was no loud music or music in the pool area The TV, DVD and CD are all of a very high standard but you will need to bring your own discs as there are none there. We were very impressed overall with the property and would recommend it to others
$1,044.00 USD total for 3 nights
Nov 8 – 11, 2026
Loved our time in Tavanier/Islamorada at Nelson's place. Location is unbeatable in the Keys if you want a peaceful place for families and able to get around to many of the islands easily but not in the more populated spots like Key West. Property is a short distance to the ocean, great pier for watching sunsets and nice restaurant. Pool was great and also had a small grill/bar. Nelson's place was super clean, comfortable, roomy, and had everything we needed, furniture was nice and comfortable. The view from the balcony is a nice wildlife refuge. Got to see adorable racoons and feral cats from a distance and balcony. Nelson was very responsive, friendly and our check-in was smooth and flexible. Nelson's condo is great for two couples, or a family. Only have 2 vehicles on property, and a hiccup was with Security. Confusion when our son, who was preapproved to visit and have dinner was turned away. Security was very rude. Nelson addressed this issue and apologized..
$1,941.75 USD total for 3 nights
Oct 26 – 29, 2026
Key West is a home away from home for our family so we have stayed in many places in the area. The Cathouse is now among our favorites. Alan was extremely helpful & communicative with booking questions. Instructions were very thorough & detailed to set us up for anything we needed to know! The space was just as pictured & described and provided us a perfect home for our stay. We had plenty of space for our guests, and there was nothing we needed that wasn’t provided. We know our way around the area fairly well and the location is set off the main strip enough for privacy but still within walking distance of wherever you need to get if you’re mobile! I have lasting images in my mind of sitting on the balcony looking out at a space that I will hold in my heart that I was able to make memories with family that will last a lifetime and I’m so grateful for what the Cathouse provided for us. We met a couple of members on our way out that were so kind and we will absolutely return!
$21,886.88 USD total for 28 nights
Jan 14 – Feb 11, 2027
Where to begin? Everything was exactly as described and pictured! Alan was incredibly responsive and quick to offer assistance. The location was close enough to easily walk to places, but the street wasn’t so busy that it interfered with sleep. My college friend and I slept so well while we stayed here. Even the construction didn’t interfere with sleeping! Finding vegan places on vacation is usually a chore. However, we found lots of EXCELLENT options, and we didn’t have to settle for a salad and an Impossible burger! I would highly recommend this place! Wendy
$847.25 USD total for 3 nights
Oct 29 – Nov 1, 2026
My family of 5 (3 kiddos ages 7-11) stayed here for a few nights while exploring the Everglades & Biscayne NP. The home was clean and well kept. It seemed like every space was well thought out. I really appreciated the k-cup supply (as our flight was real delayed and it was too late to stop at the grocery) and the NICE blow dryer ;), & cozy throw blankets to snuggle with. The outdoor table and shower and bonus balls/rackets were great!
Coastal Charm: Steps from the Beach, 2BR/2BA Condo, Pool View
$1,621.50 USD total for 7 nights
Oct 31 – Nov 7, 2026
We loved the area we were in and the condo was quiet, nice and right on the beach! It is an older property but geez the price of fancier places that are not on the beach just can’t compare to this one. We loved our stay there!!
$1,455.00 USD total for 3 nights
Oct 26 – 29, 2026
I had a truly pleasant stay at Vishakha’s property. The place was clean, well maintained, and very comfortable. Vishakha herself was an exceptional host -- warm, caring, and always ready to help. Even though the official check-in was at 1 PM, she kindly allowed me to check in early at 11 AM since I arrived around 10, which made things so much easier. On the second day, I casually mentioned that we were sneezing, and she thoughtfully prepared her special homemade besan halwa -- something she lovingly makes for her kids when they’re unwell. That personal touch really stood out and made us feel cared for. Her hospitality and kindness made the stay memorable, and I would highly recommend her property to anyone looking for a welcoming and well-kept place.
Recommended Homes in Florida Keys
Handpicked properties we think you'll love in Florida Keys.
$686.83 USD total for 3 nights
Oct 26 – 29, 2026
$692.73 USD total for 3 nights
Oct 26 – 29, 2026
$692.73 USD total for 3 nights
Oct 26 – 29, 2026
$1,679.13 USD total for 4 nights
Oct 26 – 30, 2026
$692.73 USD total for 3 nights
Oct 26 – 29, 2026
$692.73 USD total for 3 nights
Oct 26 – 29, 2026
$717.87 USD total for 3 nights
Oct 26 – 29, 2026
$2,924.00 USD total for 7 nights
Oct 26 – Nov 2, 2026
Vacation houses with pools in Florida Keys
Cool off in style with these amazing pool homes in Florida Keys.
$3,900.00 USD total for 3 nights
Mar 4 – 7, 2027
$2,140.00 USD total for 7 nights
Oct 26 – Nov 2, 2026
Casa Rosa: Historic Key West Home with Pool, 1 Block from Duval
$9,403.53 USD total for 7 nights
Jan 2 – 9, 2027
$3,813.75 USD total for 7 nights
Oct 26 – Nov 2, 2026
Tropical Sunsets: Open Gulf Views with Private Dock and Pool
$4,145.40 USD total for 7 nights
Nov 14 – 21, 2026
Waterfront Luxe Pool, Hot Tub, Theater, Games and More!
$10,743.75 USD total for 3 nights
Sep 26 – 29, 2027
$5,150.00 USD total for 4 nights
Oct 26 – 30, 2026
Pet friendly vacation rentals in Florida Keys
Bring your furry friend along! Browse pet-welcoming homes in Florida Keys.
$7,324.88 USD total for 28 nights
Mar 1 – 29, 2027
$4,819.50 USD total for 28 nights
Dec 2 – 30, 2026
$1,413.53 USD total for 3 nights
Oct 28 – 31, 2026
$8,509.50 USD total for 28 nights
Oct 26 – Nov 23, 2026
$3,606.65 USD total for 3 nights
Nov 6 – 9, 2026
$2,969.34 USD total for 3 nights
Oct 30 – Nov 2, 2026
$1,991.94 USD total for 3 nights
Oct 26 – 29, 2026
Why visit Florida Keys
Discover what makes Florida Keys a perfect vacation rental destination.
Pristine Beaches Await
Stroll on sandy shores at iconic spots.
Head to Smathers Beach in Key West, just 3.2 miles from downtown, for endless sunbathing and water activities.
Snorkeling and Diving
Explore vibrant marine life at coral reefs.
Dive at John Pennekamp Coral Reef State Park, 5 miles from Key Largo, and witness the underwater wonders.
Savor Fresh Seafood
Indulge in local catches at top eateries.
Enjoy a meal at The Fish House, famous for its fresh seafood, located 2 miles from Key Largo.
Explore Natural Parks
Discover wildlife and more outdoor adventures.
Visit the National Key Deer Refuge in Big Pine Key, just 2 miles away, for unique wildlife sightings.
Where to stay in Florida Keys
The best areas and neighborhoods for your vacation rental in Florida Keys.
Key West
Known for its vibrant nightlife and historical sites, with attractions like Ernest Hemingway Home.
Islamorada
A paradise for anglers and water sports enthusiasts, featuring the Theater of the Sea.
Marathon
Offers family-friendly fun with attractions like the Turtle Hospital and Dolphin Research Center.
Key Largo
Gateway to the Keys with renowned diving spots like Molasses Reef and John Pennekamp Park.
Find Florida Keys vacation rentals that suit your style
Vacation homes, condos, villas and more — pick the kind of Florida Keys vacation rental you want, then book it direct with the host.
Florida Keys vacation rentals with free WiFi, hot tub or air conditioning
Free WiFi, hot tub, air conditioning and more — every Florida Keys vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Florida Keys
All within driving distance of Florida Keys vacation rentals.
Smathers Beach
Famous for its long stretch of white sand, ideal for sunbathers. · 3.2 miles
John Pennekamp Coral Reef State Park
The first underwater park in the U.S., perfect for snorkeling. · 23 miles
Ernest Hemingway Home and Museum
Historic site featuring the famous writer's polydactyl cats. · 0.4 miles
Molasses Reef
A top diving destination with beautiful coral formations. · 6 miles
Turtle Hospital
A rehabilitation center for sea turtles, offering guided tours. · 44 miles
National Key Deer Refuge
Explore the protected habitat of the rare Key deer. · 20 miles
Best Time to Visit Florida Keys
Best months: Nov-Apr, with temperatures 70-80°F. Enjoy pleasant weather and low chances of rain for a perfect vacation.
The best time to visit Florida Keys is November to April, when the weather is at its best.
Getting to and around Florida Keys
Navigating the Florida Keys is easy with airports and scenic drives along US-1.
- KEY WEST INTERNATIONAL AIRPORT
- Located 2.5 miles from Key West's center, serving major airlines and regional flights.
- MIAMI INTERNATIONAL AIRPORT
- Largest nearby airport, about 110 miles from Key West. Offers diverse international and domestic flights.
- US-1 HIGHWAY
- The Overseas Highway connects all the major islands in the Keys, stretching over 113 miles.
- KEY WEST EXPRESS
- Offers ferry service from Fort Myers and Marco Island to Key West, ideal for day trippers.
Explore near Florida Keys
Cities and towns within driving distance of Florida Keys, each bookable direct with the host.
Direct with the host
Message the host before you book. Ask questions, confirm details, and deal with the person who owns the property.
Verified hosts
Every host completes identity verification before a listing goes live.
Itemised pricing
Every charge is shown before you pay — including the API connection fee, where one applies.
More vacation rental destinations around Florida Keys
Frequently asked questions
Quick answers about booking vacation rentals in Florida Keys and what direct booking on Houfy actually means.
Rental prices in the Florida Keys can vary widely, with costs ranging from $200 to over $1000 per night depending on location and amenities.
Many rentals are pet-friendly, but policies vary. Always check individual listings for pet fees and restrictions.
Popular neighborhoods include Key West for nightlife, Islamorada for fishing, and Marathon for family activities.
The best time to visit is from November to March for pleasant weather and to avoid hurricane season.
Options range from beachfront villas and cozy cottages to luxury condos and houseboats.
Rentals often provide more space, privacy, and kitchen facilities than hotels, ideal for longer stays.
Witness a turtle release or visit the lower Keys' mysterious 'blue holes,' popular with adventurers.
Houfy is a platform for direct property bookings, where guests pay the listed price directly to the owner.
Yes, Houfy is a trusted platform that enables safe and direct transactions between travelers and hosts.






























































































































































