
Vacation rentals in Florida Keys
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Private vacation rentals in Florida Keys

Florida Keys Oceanside Utopia
We spent an amazing week in the house of Kelly and Shane. The location on the waterfront is unbeatable and the house itself is super convenient, nicely remodeled and has a very cozy feel to it. We spent days in a row fishing from the dock, prepared our catch of the day on the bbq on the terrace, and caught shrimp at night which served as bait for the next day. There are great beaches, restaurants, and all kinds of day trips at hand if you wish to leave the property ;). Kelly and Shane are great hosts, with tons of tips - they clearly love the area and put great effort in the maintenance of the house and dock. They are super quick and easy in their communication and all three of us (me, husband and our 12 year old son) look forward to staying at their property again!

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
Eric reached out before we arrived to explain a few things, which made it extremely easy to get in! It’s a great location - we biked to almost everything we wanted to see within 10 minutes. Yet, it was very peaceful to sit on the front porch to have coffee in the morning. I would definitely recommend this place! We would definitely stay here again!

Houseboat Getaway In Marathon
My husband and I had such a relaxing time staying here! We felt like we were having a mini adventure, but still had all the essentials we needed. We saw manatees, dolphins, and tarpon. And we fished off the back dock at night. It was so beautiful how clear the skies were from the view of this house boat, we saw so many stars. We’ll be back again and I’m already sending the link to friends who were asking about our stay!

Beach House, Private Pool & Dock, Gulf Sunset view
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!

Cozy Waterfront Retreat w/ Private Boat Dock +Tiki
The RV was perfect for my husband, sister and I. We especially loved the tiki dock where we hung out. Watching sunrises with our coffee was a great way to start each day’s adventures. Ramses was very communicative and made sure the check-in form was completed so everything went smoothly for us. All in all a great experience!

Trip Around the Sun 2/2 + dockage & cabana club
We absolutely loved our stay and would book this place again! The beds were incredibly comfortable! The house, especially the kitchen, is stocked with everything you will need and more! A boat launch is down the street within the Key Colony community, which was perfect! Peaceful back patio area with a pretty view on the canal. The house includes very impressive upgrades, so nicely done!!

6. Waterfront Key Largo Studio, Near Kayaks & Reef
Beautiful place to live. Perfect location. Even saw a manatee and a shark from the backyard. Wonderful hosts also. Thank you for everything!

Quiet tropical Oasis setting with 1 bed and 1 bath
We had a great time! Close enough to Miami without actually staying in Miami, and very close to the two National Parks. The place was cozy and exactly what we needed for our stay!
Houses in Florida Keys

Cancellation Deal: 07/26 thru 08/09
Eddie’s place was perfect for our family vacation! It was beautifully furnished and decorated. The house was clean and clutter free. There were plenty of linens and towels. The kitchen had everything you need and was well organized. The pool area was so relaxing. The location was incredibly convenient to grocery stores and activities as well as just a short walk to the beach which also had a park and great playground for kids. We hope to come back again soon!

Your Keys Getaway!
My husband and I stayed here during a trip to Key Largo at a friend’s destination wedding at the Lighthouse. It was only a 5 min drive to the venue which was very convenient. The street was so unbelievably quiet given how close it is to the main stretch of highway. We stayed out on the balcony for over an hour one night and only 2 cars drove by the whole time. Conveniently located to a lot of delicious restaurants. Ana was responsive. The place was clean and cozy. Not near any water and there is no access to it, which she does state clearly in the description but the photo makes you think maybe you can walk to the water. However, that area (in the photo) is restricted so you can’t access it. Luckily, in Key Largo, there’s plenty of places to visit that are on the water, so it wasn’t too much of a bummer. It was a clean, quiet, private, and cozy place to crash for the few days we were there which was exactly what we were looking for. And I appreciated the huge mirror! Recommend.

Endless Summer
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.

Viamarhe House-Private beach, Kayak, yard games
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Rise And Shine On The Water
There were five of us in the house and we felt immediately comfortable. Everything was super clean. The location right on the water was overwhelming as expected. Everything that is needed was there. The kitchen and terrace were very large and the mattresses were very comfortable. Key West is about 30 minutes away. Check-in and check-out as well as contact were completely unproblematic. We will be back!

Captain’s Quarters Ahoy Mateys! Florida, Keys
Leila was very helpful and friendly. Made sure we were arrived and didn’t need anything. Place was very clean. Has everything you need in the kitchen. Comfortable. Stayed with another couple, plenty of space. Paddle boarded right off the dock. Great central location to enjoy all the keys. Would definitely recommend.

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
We spent a great weekend at Elisabeth's house. The house is centrally located on Key Largo and has access to a nice private beach area that is perfect for watching sunsets and fishing. The house was ideal for our larger group with lots of amenities and everything we needed to host for the weekend. Highly recommend!

Anglers Terrace, Condé Nast Traveler's Best Airbnb
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
Family friendly vacation rentals in Florida Keys

May availability 70ft Dock, Near Beach VACA23-16
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!

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish
We all had a great time and the house was gorgeous! The house had everything we needed for a pool day or a fishing day. The location is great and has everything you need around. The host even sent key lime pies from Sweet Savannah’s (walking distance) as a sweet gesture after needing a few people to stop by to fix something outside. We can’t wait to stay again!

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

Key Largo Waterfront Home with Tiki & Boat Dock
We have found our home away from home when we visit the Keys! Penny’s house was not only exactly as described, but something about it just felt like home. We came home and immediately booked another stay. Penny was responsive, friendly and we enjoyed sending her pictures from our stay. Our daughter is 4 and learned how to fish during our stay - The core memories were endless! We enjoyed daily manatee visits, so much fishing, and visiting local restaurants! Princess the sweet community kitty has a special place in our heart, please feed her during your stay :)

Best JW Marriott Alternative Prime~ Location~Pool
Amazing location with a very “homey” atmosphere. Genuinely one of if not my favorite airbnb I have ever stayed in. Immediately feel at home when you walk in and enjoy an easy walk to the gorgeous Marco island beach, or grab food at the Marriott. Truly a gem 💎 We will 100% be back.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
We came to Naomi’s listing. We did not know much about the location. Everything was within walking distance. Naomi communicated effectively. We will be here again.

⭐ Rare Waterfront Western Exposure Vacation Home
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.

Hunter 26 Sailboat
We had such a unique and memorable experience staying on this boat in Miami! Everything was clean, cozy, and exactly as described. One of the highlights of our trip was watching the sunrise while kayaking… such a peaceful and beautiful way to start the day, and the provided kayaks made it super easy to enjoy the water. The host was responsive and made sure we had everything we needed. Highly recommend this stay if you’re looking for something different. Will be returning!!
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.
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- Bayfront Park
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Trump National Doral Miami
- Crandon Beach
- Phillip and Patricia Frost Museum of Science
- Key Biscayne Beach
- Coral Castle
- Hobie Island Beach Park North
- Biscayne National Park
- Fairchild Tropical Botanic Garden
- Conch Key
- Biltmore Golf Course Miami
- Cannon Beach
- Venetian Pool
- Miami Seaquarium
- EAA Air Museum
- Cocoa Plum Beach
- Matheson Hammock Park
- Monkey Jungle
- Sea Oats Beach
- Far Beach
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