Vacation rentals in Florida Keys

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Top-rated vacation rentals in Florida Keys

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Top guest favorite
A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.
Cottage in Cudjoe Key
4.94 out of 5 average rating, 159 reviews

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Top guest favorite
A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Multiple boats are docked along the marina, with silhouettes of masts against the colorful sky, creating a peaceful atmosphere ideal for relaxation.
Home in Key Largo
4.98 out of 5 average rating, 231 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Superhost
A serene outdoor seating area is presented with two cushioned sofas and a wooden coffee table, overlooking a waterfront. The sunset creates a vibrant orange and yellow backdrop, reflecting off the water. Additional seating in the distance enhances the tranquil atmosphere of the space.
Camper/RV in Key Largo
4.93 out of 5 average rating, 134 reviews

Paradise Casa Bayfront sunsets,pool,King bed ,dock

Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

Top guest favorite
A sunset view is captured from a covered outdoor seating area, showcasing a tranquil waterway. Silhouettes of kayaks and a table are visible, while the setting sun creates a warm glow across the horizon. Natural textures are evident in the thatched roof above.
Tiny home in Key Largo
4.97 out of 5 average rating, 190 reviews

Oasis2 in Key Largo With a million dollar view

Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Top guest favorite
The image features a distant houseboat silhouetted against a vibrant sunset, reflecting shades of orange and purple on the water's surface. The view is taken from a skiff, with gentle ripples seen in the foreground, creating a serene atmosphere.
Boat in Islamorada
4.93 out of 5 average rating, 372 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Superhost
A serene beach area is highlighted by sandy shores and gentle waves. Palm trees sway in the breeze, while lounge chairs are arranged neatly in the foreground. A wooden dock extends into the water, framed by lush greenery in the background.
Home in Key Largo
4.79 out of 5 average rating, 153 reviews

Escape to the Seaside!

Our 2-story ocean front home is a quite and tranquil oasis. Centrally located in south Key Largo, allows for easy travel to the lower Keys. Our home is decorated in a casual coastal style to provide a comfortable and relax setting. Upstairs is 3 bedroom 2 baths and spacious open concept living room, dining room and kitchen. It provides all the comforts of home. Equipped with flat screen TV, complimentary Wi-Fi and premium cable programming. Here, you’ll have everything you need.

Superhost
Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.
Villa in Marathon
4.89 out of 5 average rating, 505 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Top guest favorite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
5 out of 5 average rating, 183 reviews

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Top guest favorite
A vibrant sunset casts a warm glow over the outdoor area featuring a sheltered gazebo, surrounded by lush greenery and reflective water. Nearby, a modern living room is furnished with comfortable seating and a large screen, creating an inviting space for relaxation.
Home in Marathon
4.95 out of 5 average rating, 112 reviews

Coco Plum Waterfront Hideaway Home in Marathon

This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.

Top guest favorite
A two-story duplex is set amidst palm trees, featuring a blue exterior and multiple balconies. A vehicle is parked in the driveway, with a pathway leading towards the entrance, surrounded by landscaped areas that include gravel and greenery.
Home in Key Largo
4.92 out of 5 average rating, 185 reviews

Blue House Marine in Key Largo

The house is a Duplex style house for guest it is very quite and private it has 3 bedrooms and two bathrooms kitchen living room and dining area also a walk around balcony its screen in, it has 2 queen style beds and two twin beds. the home has been remodel you have canal views and open ocean viewsfull bathroom by the pool, barbecue area table and chairs for dining plus out door furniture. P.S There is no longer pool heating

Top guest favorite
Home in Marathon
4.94 out of 5 average rating, 197 reviews

Spacious 3Br/3Ba, 70ft Dock, March avail VACA23-16

Enjoy the boutique decor of our large, spacious home. Our place is a short distance from Sombrero Beach, with bicycles available to ride there. Our property is on a wide and deep canal, with both ocean and gulf access. Our dock is 70 ft, so ideal place for large boats, or you can even bring 2 boats. Free parking, with space to park boat trailer. We include free passes to the Sea Turtle Hospital to guests.

Top guest favorite
A private swimming pool is surrounded by a stone patio, featuring two lounge chairs for relaxation. The landscaped garden includes tropical palm trees and lush plants. The two-story home stands in the background, with a shaded balcony above the patio area, providing outdoor seating options.
Villa in Duck Key
4.99 out of 5 average rating, 107 reviews

★Beautiful Gated Oasis★with private pool and patio

Enjoy a great family vacation with the conveniences of a modern home in this beautifully decorated gated house with private pool and patio, carport, 70" 4K Smart TV, high speed internet - 1,000 mbps, and fully equipped kitchen. Close to tropical activities and great restaurants. Relax, bond, and make new memories in the Florida Keys.

Popular amenities for Florida Keys vacation rentals

Frequently Asked Questions

  • Where is Florida Keys located?

    Florida Keys is a chain of islands stretching off the southern tip of Florida, surrounded by the Atlantic Ocean and Gulf of Mexico. The area is known for tropical scenery, marine life, and distinct communities rooted in maritime traditions.

  • When is the best time to visit Florida Keys?

    Visitors often favor late winter and spring for milder temperatures around 66–81°F (19–27°C) and lighter rainfall. Summer months can be warmer, reaching near 91°F (33°C), with more frequent showers, but activities continue year-round.

  • What are some things to do near Florida Keys?

    You can explore local coral reefs by snorkeling or diving, visit historic sites in Key West, and enjoy kayaking or fishing around the islands. The region also has public beaches, galleries, and culinary experiences shaped by coastal influences.

  • How is the weather near Florida Keys?

    Florida Keys has a subtropical climate, with winter temperatures near 61–76°F (16–25°C) and warmer summers reaching 78–91°F (25–33°C). Rain is more frequent from May to October, so light clothing and sun protection are recommended throughout the year.

All about 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.

What are the 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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