Skip to content

Vacation rentals in Florida Keys

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Florida Keys

Guests agree: these stays are highly rated for location, cleanliness, and more.

Waterfront Villa-Bring Your Boat Cabana Club Beach
Entire residential home · 5 guests · 3 beds · 2 baths

Waterfront Villa-Bring Your Boat Cabana Club BeachNew Listing! Beautiful, clean 2/2 villa with 40ft dock- bring your boat up to 50ft. Open concept with water views, great location in beautiful Key Colony Beach, walk to the beach, pool and tiki bar at the Cabana Club (membership included with the rental), close to Marathon and centrally located between Islamorada and Key West. Relax and grill on the back patio or use of our ocean kayaks on the beautiful canal. 10 minute ocean and gulf access, close to restaurants, shopping and nightlife.

Old Island Life
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Old Island LifeThis place is like the old island days. Separate living quarters from the bath house. It’s not the Hilton. The Hilton is available 30 miles South in Key West. This place is located in the National Key Deer Refuge on Big Pine Key. We can guarantee deer sightings. We are in a jungle with a few jungle critters. Nothing that can’t be dealt with, or lived with. Has small refrigerator, microwave, cable tv, and WIFI.

Private waterfront sleeps 10 dock heated pool pets
SUPERHOST
Entire residential home · 10 guests · 6 beds · 2 baths

Private waterfront sleeps 10 dock heated pool petsBeautiful waterfront home, sleeping 10, in the heart of Marathon. Private setting with over 2 acres of land. Plenty of parking for cars, trailers or RVs. Protected dockage for multiple small or large boats. Perfect for a family trip or fisherman's getaway. Pet-Friendly. Families can enjoy the space with a heated pool, outside grill, and sunset views. Cook your catch! Working from home? Make our home with high-speed WiFi your waterfront workspace. Pet friendly.

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Florida Keys vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Florida Keys

SUPERHOST
  1. Private room
  2. Key West
Old Town - Room Opens to Pool and Garden
R2,952 ZAR per night
SUPERHOST
  1. Entire guesthouse
  2. Key Colony Beach
Last minute deals! Paradise found! 3/2 Key Colony
R2,194 ZAR per night
SUPERHOST
  1. Private room
  2. Marathon
Casa Mariposa: Easy walk to Sombrero Beach
R2,493 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Pulpo Cottage
R1,791 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Marathon
Cozy Keys Efficiency 8a
R2,655 ZAR per night
SUPERHOST
  1. Entire guesthouse
  2. Big Pine Key
Beautiful private camper situated amongst nature
R1,334 ZAR per night
SUPERHOST
  1. Entire townhouse
  2. Marathon
KCB Waterfront Split Home Walkable to Cabana Club
R2,373 ZAR per night
SUPERHOST
  1. Entire condominium (condo)
  2. Marathon
Sombrero Beach Tropical Getaway
R2,225 ZAR per night
SUPERHOST
  1. Private room
  2. Marathon
Casa Mariposa: Sombrero Beach Neighborhood
R2,198 ZAR per night
SUPERHOST
  1. Entire townhouse
  2. Islamorada
Waterfront Townhouse in Islamorada with Boat Slip
R3,245 ZAR per night
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Manta Cottage
R1,991 ZAR per night
SUPERHOST
  1. Entire condominium (condo)
  2. Key Colony Beach
Beachside Unit 07 - Come Enjoy Our Private Beach
R2,608 ZAR per night

Top-rated things to do in Florida Keys

Unique activities hosted by local experts vetted for quality

  • Clear Kayak Tour in the Florida Keys
    We'll get you checked in right when you arrive to allow for the most possible time on the water! Once you're all checked in, we'll give some basic paddle instructions and information about the tour ahead. We'll get you loaded up into your clear kayak and off we go! The paddle will last about 2 to 2.5 hours depending on the speed of our group and any wildlife we may see along the way. We will be sure to take plenty of pictures and give some awesome, unique facts about the area on our several picturesque stopping points! The first half of the paddle will be in the open grass flats and the second half will be a secluded maze of mangrove tunnels. Be ready for lots of great local nature and wildlife along the way! Other things to note AirBnB does not collect taxes but we owe taxes so that has been included in the price as well! Check out our website for additional times.
    From Price:R945 / person
  • Reef Snorkel & Sunset Sail
    We will snorkel the reef and enjoy the sunset while sailing on a spacious and fun sailing catamaran. You will also get to enjoy fresh organic fruit, veggies and hummus from our favorite local organic cafe, Date and Thyme. Florida’s Barrier Reef is right off the coast of Key West. We only provide this trip during a limited time, June through September, because we want to snorkel the reef when the weather is just right. Explore the wondrous wildlife of the reef with one of our biologists. It truly is one of the most beautiful places you need to see while in the keys. Sailing, the original form of renewable energy transportation! I am on a mission to spread the value of conservation and I think amazing nature experiences with a knowledgeable biologist is the best way to do that! But sometimes all you need to do to appreciate nature is go sailing and watch a sunset! Other things to note Meet at the boat 15 minutes before departure. Call or text my wife Jen with any questions. 305-294-6306.
    From Price:R1,461 / person
  • Historic Seaport Food And Walking Tour
    Explore the colorful docks and side streets of Key West visiting 5+ locally-owned eateries to taste our traditional fruits of the sea! This tour includes locally caught fresh fish tacos, decadent lobster mac n cheese, an authentic Cuban sandwich, peel-n-eat pink shrimp, award winning key lime pie, and a glass of wine. Expect tasty historical tidbits to accompany the entire 3 hour, 1.5 mile adventure along our Historic Seaport. What to Expect -Five or more tastings: Come hungry. -Generous tastings of fresh, local seafood like Key West pink shrimp, local lobster, and more! Pork and beef substitutions available. Sorry, no chicken or vegetarian options. -Listen to the history and origin of our Historic Seaport and the industries that shaped the island -Walk off the beaten path of Duval Street and into historic neighborhoods and hidden gems -Learn unique fun facts and the history of Key West from knowledgable locals -This three-hour tour is moderately paced, and covers a little over a mile of walking distance. Suitable for most fitness levels. COVID Safety Precautions: Guaranteed groups of 10 or less. We will wear masks according to local mandates. Spreading out: We will help you stretch out & most of our tour is outdoors, but we may be required to sit indoors
    From Price:R1,195 / person
  • Biologist Guided Dolphin Watch & Snorkel
    You will meet me at my electric catamaran, Squid, under our HONEST ECO sign. If you do not see a time or date that works for you let me know! I can probably figure something out. We will depart from the dock located at the Historic Seaport. We will then head out on the water to an area that I know which provides a year round home for about 200 wild Bottlenose Dolphins. This is my moment to share the wonders of these marine mammals with you, while always operating my vessel in a manner that is safe and respectful of the dolphins and their need for space. With the right know-how I can usually find dolphins in under an hour and in calm waters. After observing the dolphins many different behaviors from the boat we will head to one of my favorite spots to snorkel with sponges, coral heads or a patch reef. I will take you to the best place with the best visibility that day. I'll be your guide, leading you around a calm snorkeling spot and point out animals that make our ecosystem unique and answer any questions that you have. Other things to note Check in at the HONEST ECO boat Squid. The maximum number of guests I have on board is usually around 15 guests. I can take up to 24 guests on a private charter.
    From Price:R1,608 / person
  • Bar Hop like a Local - Off Duval Street
    We'll veer vacationing drinkers off the infamous Duval Street into some of the city’s best, most locally loved bars to sample fresh spins on old classics. Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and explore the sights, sounds, and “intoxicating” flavors of the tiki era, each of it’s 5 stops revealing a new secret. This bar hop is is about getting off touristy Duval Street and into local watering holes! What To Expect: -5 stops with preselected drinks featuring: a craft draft cocktail, a Hemingway Daiquiri, a locally made beer, a tiki drink, and a signature margarita. -Tantalizing food tastings and historical tidbits to accompany your cocktails. -Relax as an expert local guide takes you on an escape through the hustle and bustle of Key West’s Old Town. -The ultimate 3 hr happy hour experience in Key West. -Complimentary Food Tour booklet packed with coupons and recommended eateries included! Other things to note -Drinks are preselected. No substitutions. Any drink options not included must be purchased. -No dietary preferences or restrictions can be accommodated. -Operates rain or shine! Ponchos provided. COVID Safety Precautions: Guaranteed groups of 10 or less. We will wear masks according to local mandates. Spreading out: We will help you stretch out & most of our tour is outdoors, but we may be required to sit indoors
    From Price:R1,195 / person

Nearby destinations