Best Vacation rentals and Airbnb offers in Florida Keys, FL
9.6 24 reviews
Florida Keys, FL
08/22 – 08/23
$371/nightfor 1 night
2bd/1ba Waterfront Retreat W/35’ Dock
1 2
apartment , Cudjoe Key
This Cudjoe Key waterfront cottage, situated in the Venture Out community, provides easy access to local restaurants like the Square Grouper and the Niles Road Nature Trail. The two-bedroom, one-bathroom house sleeps five, boasting a pool, jacuzzi, full kitchen, and internet access, plus nearby tennis, basketball, and pickleball courts.
9.6 121 reviews
Florida Keys, FL
11/25 – 11/27
$718/nighttotal: $1436 (2 )
Villa 5053 On Duck Key Boat Slip Available - 2bd 2.5ba
2 6
apartment , Duck Key
This waterfront vacation home in Duck Key is located within 2 miles of Little Conch Key, Curry Hammock State Park, and Walkers Island, offering easy access to nearby attractions. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. This two-bedroom house is perfect for a small family or group of friends, offering 900 square feet of space and comfortably accommodating up to 6 guests. The house features a fully equipped kitchen, a terrace or balcony, a garden, parking, and free Wi-Fi, making it ideal for a relaxing and enjoyable stay.
10 2 reviews
Florida Keys, FL
07/24 – 07/27
$890/nighttotal: $2670 (3 )
🌴Ms. Marriott’s 12+beds Luxury Stay.
1 14
house , Kendall
This multi-family home in Kendall, located just off the expressway and less than 1 mile from Zoo Miami, offers flexible rental options for groups of up to 19 guests. This property features a SwimSpa, a huge courtyard, and 3 kitchens, making it ideal for large gatherings, with easy access to Miami Beaches, the Everglades, and Florida Keys-Key West.
9.5 438 reviews
Florida Keys, FL
11/25 – 11/27
$574/nighttotal: $1148 (2 )
Save Big $$$ May!! Waterfront 4 Bikes & 2-2 Person Kayaks. King & Queen Beds
2 6
apartment , Cudjoe Key
This vacation home is located in Summerland Key, just a short walk from Venture Key and Venture Out Keys, offering easy access to local attractions and activities. It has received excellent ratings for location, cleanliness, and overall user experience. The 2-bedroom, 2-bathroom home spans 860 square feet and can comfortably accommodate up to 6 guests. Enjoy a range of amenities including a private pool, spa, tennis court, and a fully equipped kitchen, perfect for creating memorable vacation experiences.
8.6 84 reviews
Florida Keys, FL
06/20 – 06/27
$261/nighttotal: $1827 (7 )
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West
2 2
cottage , Cudjoe Key
This waterfront cottage is located on Cudjoe Key, just a short drive from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering easy access to popular attractions and activities. It has received very good user ratings, making it a popular choice for travelers. The cottage has two bedrooms and one bathroom, providing comfortable accommodations for up to four guests. It features a fully equipped kitchen, a private pool, a terrace, a garden, and laundry facilities for a convenient and enjoyable stay.
9.4 83 reviews
Florida Keys, FL
06/20 – 06/27
$310/nighttotal: $2170 (7 )
Beachside Unit 25 - Key Colony
1 1
apartment , Key Colony Beach
This Key Colony Beach apartment is a short walk from Sunset Park and Coco Plum Beaches, offering easy access to the stunning Florida Keys coastline. The apartment has received excellent ratings for location, cleanliness, and overall experience. The 460 square foot apartment comfortably sleeps two guests and features a fully equipped kitchen, a private balcony, and access to a swimming pool. Enjoy the convenience of on-site parking, barbecue grills, and a quiet location perfect for a relaxing getaway.
Florida Keys, FL
08/04 – 08/07
$405/nighttotal: $1215 (3 )
Bungalow W/ Free Kayaks, Sailboat, Bicycle Use
1 4
cottage , Key Largo
This Key Largo cottage is a 15-minute walk from Jimmy Johnson's Big Chill and Jacob's Aquatic Center, and within 3 miles of Bluefin Rock Harbor Marina and North Nest Key. This 220-square-foot one-bedroom, one-bathroom unit sleeps four and features a kitchenette with a refrigerator, stovetop, and microwave.
9.6 127 reviews
Florida Keys, FL
06/20 – 06/27
$358/nighttotal: $2506 (7 )
Luxury Condominium In Key Largo... Sunsets, Marina
2 1
apartment , Key Largo
This renovated fourth-floor condo in the Kawama Yacht Club, a gated community in Key Largo, offers ocean views and direct ocean access, situated within 2 miles of John Pennekamp Coral Reef State Park and Dagny Johnson Key Largo Hammock Botanical State Park. This 1190 square foot, two-bedroom, two-bathroom unit accommodates up to 8 guests and features a fully equipped modern kitchen, a private balcony with ocean views, a swimming pool, spa, garden, and complimentary boat ramp access.
10 67 reviews
Florida Keys, FL
06/20 – 06/27
$309/nighttotal: $2163 (7 )
Waterfront Islamorada Condo Heated Pool, Marina & Deeded Boat Slip
2 5
apartment , Islamorada, Village of Islands
This Islamorada condo, located at mile marker 88.5, offers access to Robbie's Marina and Theater of the Sea, with Miami 67 miles north. This 950 square foot apartment sleeps 6 guests and features 2 bedrooms, 2 bathrooms, a full kitchen, a private balcony, and access to resort amenities including a heated pool, tennis courts, and a deeded boat slip with water and electric.
9.2 358 reviews
Florida Keys, FL
06/19 – 06/23
$305/nighttotal: $1220 (4 )
Ocean View Condo With Balcony/marina View
2 4
apartment , Tavernier
This 2-bedroom apartment is located in Tavernier, a short 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys beaches and a peaceful retreat from the hustle and bustle. The apartment has excellent user, location, and cleanliness ratings. The 860-square-foot apartment can comfortably accommodate up to 6 guests. Amenities include a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a sauna, a tennis court, and free parking.
10 27 reviews
Florida Keys, FL
11/25 – 11/27
$784/nighttotal: $1568 (2 )
Treehouse De Lujo | Amplio Parqueo |
1 6
apartment , Islamorada, Village of Islands
This secluded wooden treehouse rental in Tavernier, Islamorada, Village of Islands, offers a private escape just minutes from Upper Florida Keys attractions like world-class fishing and diving. This 4-bedroom, 2-bathroom vacation home accommodates up to 8 guests with a kitchen, air conditioning, Wi-Fi, and a Tesla-compatible EV charging station, plus ample parking for a boat trailer up to 30 feet.
9.5 109 reviews
Florida Keys, FL
11/25 – 11/27
$681/nighttotal: $1362 (2 )
Waterfront Duck Key Villa - Sleeps 6
2 6
apartment , Duck Key
This two-bedroom house is conveniently located in Marathon, Florida, just a short drive from Duck Key and within 5 kilometers of popular destinations like Little Conch Key, Curry Hammock State Park, and Walkers Island. The house has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travelers seeking a comfortable and enjoyable stay. The house offers ample space for up to 6 guests with three bathrooms, and includes amenities such as a fully equipped kitchen, internet access, air conditioning, a garden, and parking. Enjoy the peaceful setting near Curry Hammock and Long Key State Parks, perfect for outdoor enthusiasts, and explore the nearby attractions with ease.
Best family friendly Florida Keys, FL vacation rentals
Among the 11639 accommodations in Florida Keys, FL, here are the 4 best family friendly rentals
9.8 168 reviews
Florida Keys, FL
07/31 – 08/03
$239/nighttotal: $717 (3 )
Ocean Blue Condo, Key Colony Beach Heated Pool
1 2
apartment , Key Colony Beach
This oceanfront Key Colony Beach studio condo boasts private beach access and adjacency to Sunset Park. The fully renovated 1-bedroom unit sleeps 2 guests, offering a king-sized bed, modern bathroom, fully equipped kitchen, and access to a heated pool, BBQ grills, and kayak/bicycle rentals via Wheels-2-Go.
9.6 86 reviews
Florida Keys, FL
08/04 – 08/07
$296/nighttotal: $888 (3 )
Welcome To Paradise!
1 4
apartment , Key Largo
This oceanfront Key Largo apartment is located in the gated Kawama Yacht Club community, just a short walk from the beach and close to John Pennekamp Coral Reef State Park and Dagny Johnson Key Largo Hammock Botanical State Park. This highly-rated rental receives excellent reviews from previous guests. The apartment is a one-bedroom, one-bathroom unit with a 900 square foot floor plan that comfortably accommodates up to four guests. The apartment offers a range of amenities, including a private balcony overlooking a nature preserve, access to a resort-style community with multiple swimming pools, a saltwater lagoon, tennis courts, a fishing jetty, and a playground.
9.6 145 reviews
Florida Keys, FL
08/22 – 08/23
$645/nightfor 1 night
Villa 5023 On Duck Key Boat Slip Available - 2bd 1.5ba
2 2
apartment , Duck Key
This waterfront vacation home in Duck Key is surrounded by popular attractions like Little Conch Key, Curry Hammock State Park, and Walkers Island. It has received excellent ratings for its location, cleanliness, and guest experience. The house has two bedrooms, a sofa bed, and can accommodate up to 5 guests. It has a floor area of 780 square feet. The fully equipped kitchen features modern appliances for convenient meal preparation. The house also has a private garden for relaxation and outdoor enjoyment.
9.6 53 reviews
Florida Keys, FL
06/20 – 06/27
$216/nighttotal: $1512 (7 )
Convenient Central Marathon Location, Canal View.
1 2
apartment , Marathon
This Marathon Shores vacation home is located within a 10-minute walk of Captain Hooks Marina and Dive Center, Coco Plum Beach, and San Pablo Catholic Church. The one-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen, a barbecue grill, a terrace, and a garden.
Best Florida Keys, FL vacation rentals with a pool
Among the 11639 accommodations in Florida Keys, FL, here are the 4 best rentals with a pool
10 2 reviews
Florida Keys, FL
08/22 – 08/23
$363/nightfor 1 night
Private Beach! Ocean View Suite W/ Full Kitchen! Outdoor Pool + Free Parking
1 2
apartment , Tavernier
This Tavernier apartment rental boasts beachfront proximity, a 10-minute walk from Harry Harris Park and a 6-minute drive from the Florida Keys Dive Center. The 1170-square-foot unit features two bedrooms, two bathrooms, a fully equipped kitchen, and access to a shared pool, garden, and concierge services.
9.6 382 reviews
Florida Keys, FL
07/26 – 08/01
$429/nighttotal: $2574 (6 )
May-aug '26 Deals! Oceanfront Lux 1350sf, Stunning Views& All Amenities Of Home!
2 4
apartment , Key Largo
This beachfront apartment is located in Key Largo's city center, just a mile from Baker's Cay Resort Beach and Jimmy Johnson's Big Chill, with Bluefin Rock Harbor Marina and North Nest Key within a three-mile radius. The apartment has excellent user, location, and cleanliness ratings. This 1350 square foot apartment comfortably sleeps 6 guests in two bedrooms and two bathrooms. The apartment features a private pool, a fully equipped kitchen, free WiFi, a DVD player, and housekeeping services.
10 396 reviews
Florida Keys, FL
09/08 – 09/10
$305/nighttotal: $610 (2 )
New Listing! Quaint Spanish Colonial House Gateway To The Fl Keys & Everglades
3 2
apartment , Leisure City
This apartment is located in Leisure City, a quiet neighborhood bordering the Redland tropical agricultural area, with easy access to the Everglades National Park, Biscayne National Park, Fruit & Spice Park, and the Florida Keys. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This spacious 1800 square foot vacation rental comfortably accommodates up to 12 guests in its three bedrooms and two bathrooms. Enjoy the Florida weather on the large patio, take a dip in the swimming pool, or relax in the garden while having access to a full kitchen, air conditioning, internet, and parking.
9.7 34 reviews
Florida Keys, FL
06/20 – 06/27
$450/nighttotal: $3150 (7 )
Reel Paradise Ii - Updated 2bed/2bath With Brand New Private Pool & Dockage
2 5
apartment , Marathon
This Marathon vacation home is located just a short distance from Captain Hooks Marina and Dive Center, Coco Plum Beach, and San Pablo Catholic Church, offering easy access to local attractions and activities. The property has earned excellent ratings for location, cleanliness, and overall user experience. This two-bedroom house comfortably accommodates up to six guests, with a sofa bed available for additional sleeping arrangements. The home offers a fully equipped kitchen, a private pool, a terrace, a garden, and parking, providing everything you need for a relaxing and enjoyable stay.
Frequently Asked Questions about vacation rentals in Florida Keys, FL
What are the must-see sights in the Florida Keys, FL, United States?
The Florida Keys offer a plethora of iconic sights. Key West is a must, with its historic Mallory Square for sunset celebrations, Ernest Hemingway's Home and Museum, and the iconic Southernmost Point Buoy. Further up the Keys, you'll find the Seven Mile Bridge, a stunning engineering feat offering breathtaking views, and Bahia Honda State Park, known for its pristine beaches and snorkeling opportunities. Don't miss exploring the charming towns along the Overseas Highway, each with its own unique character.
What are the best Airbnb and vacation rentals in Florida Keys, FL?
There is a wide range of vacation rentals available in Florida. You can stay in a luxury villa in Cape Coral with stunning views over the water, a townhouse in Orlando, an apartment in Miami, just to name a few of your destinations and options available. We can help you find the perfect Florida vacation rental for you and your budget in seconds.
Are there unique natural phenomena in the Florida Keys, FL, United States?
Absolutely! The Keys are known for their vibrant coral reefs, part of the third-largest barrier reef system in the world. You can witness incredible marine life while snorkeling or diving. The unique ecosystem also supports diverse bird populations, making birdwatching a popular activity. Additionally, the area experiences stunning sunsets, particularly at Mallory Square in Key West.
What are the most popular Airbnbs in Florida Keys, FL?
Are there any unusual vacation rentals in Florida?
Yes! Stay in a modern castle in Fort Lauderdale, a floating cottage in Sanford, a treehouse in the woods, or even a yurt with its own deck in Port St. Joe. You can find many quirky and unusual vacation rentals in Florida, and we can help you find the one you're looking for!
What essentials should you bring along for a trip to the Florida Keys, FL, United States?
Pack light clothing, swimwear, sunscreen (essential!), sunglasses, a hat, and insect repellent. Comfortable walking shoes are a must, as are water bottles to stay hydrated in the Florida heat. Don't forget your camera to capture the stunning scenery and marine life. If you plan on water activities, bring appropriate gear like snorkeling equipment or water shoes.
What are the best vacation rentals with a pool in Florida Keys, FL?
Top destinations in Florida include Sarasota, Orlando-Walt Disney World, St. Petersburg, FL, Key West, Naples, and Miami Beach.Florida's beaches are huge attractions, with the most popular being South Beach, Fort Lauderdale Beach, and Clearwater Beach. Of course, theme parks are a big draw for Florida, but you don't just have Walt Disney World, but also the Wizarding World of Harry Potter, Busch Gardens, and Universal Studios Florida. Art and culture lovers may want to visit the Salvador Dali Museum in St. Petersburg or the Hemingway House in Key West. Nature lovers will want to visit Dry Tortugas National Park or the Naples Botanical Garden.
What famous events or festivals are happening in the Florida Keys, FL, United States?
The Florida Keys host many events throughout the year. Key West's Fantasy Fest is a popular Halloween celebration, known for its vibrant costumes and parades. The Conch Republic Independence Celebration in Key West is another quirky and fun event. Numerous smaller festivals and events are held throughout the Keys, often centered around local seafood and maritime traditions. Check local listings for specific dates.
What are the best rentals for families and kids in Florida Keys, FL?
Some typical Florida dishes to try are conch fritters, a type of sea snail that's fried in batter shrimp and grits, fried gator tail, Key lime pie, oysters, and ceviche. However, when in doubt, you can never go wrong with freshly caught fish.
What is the average daily budget you should plan for (accommodation, food, transportation, activities) in the Florida Keys, FL, United States?
A daily budget will vary greatly depending on your travel style. For a budget-conscious trip, you could manage on around $150-$250 per day, covering basic accommodation, casual meals, and some activities. Mid-range travelers might spend $300-$500 per day, while luxury travelers could easily exceed $1000 per day. Transportation costs will depend on whether you rent a car or use other methods.
What are the best rentals or Airbnbs with a jacuzzi in Florida Keys, FL?
Where can you find the best restaurants serving local dishes in the Florida Keys, FL, United States, and what are the must-try specialties?
The Keys boast many excellent seafood restaurants. Look for places specializing in fresh, locally caught fish. Key West has many options, but exploring smaller towns along the Overseas Highway often reveals hidden gems. Must-try dishes include fresh Key West pink shrimp, stone crab claws (seasonal), and conch fritters. Many restaurants offer local variations on Caribbean cuisine.
What are some less-famous attractions in the Florida Keys, FL, United States that are worth the visit?
Consider visiting the Turtle Hospital in Marathon, which rehabilitates injured sea turtles. The History of Diving Museum in Islamorada offers a fascinating glimpse into underwater exploration. Exploring the smaller, less-visited islands and beaches along the Overseas Highway can offer a more secluded and peaceful experience. Check out local guides for hidden coves and snorkeling spots.
What are the best activities for engaging with locals and understanding their culture in the Florida Keys, FL, United States?
Visiting local markets, attending community events, and chatting with staff at smaller, family-run businesses can offer a more authentic cultural experience. Consider taking a guided tour that focuses on local history and traditions. Many smaller towns host regular events that showcase local arts and crafts.
What unique natural landscapes and terrain features can travelers explore in the Florida Keys, FL, United States?
The Florida Keys' unique landscape is defined by its low-lying islands, mangrove forests, and of course, the coral reefs. Exploring the various state parks offers opportunities to hike, bike, and kayak through these diverse ecosystems. The beaches vary from fine white sand to rocky shores, each offering a different experience.
How many days are ideal for visiting the Florida Keys, FL, United States, and what are some itinerary suggestions?
A week is a good amount of time to explore the Keys thoroughly, allowing you to visit Key West and several other islands at a leisurely pace. A shorter trip (3-4 days) can focus on Key West and the immediate surrounding areas. Many itineraries center around driving the Overseas Highway, stopping at various points of interest along the way. Consider splitting your time between exploring Key West's attractions and enjoying the natural beauty of the other islands.
How is the weather in the Florida Keys, FL, United States during high season?
High season (generally November to April) offers warm, sunny weather, ideal for outdoor activities. Temperatures typically range from the low 70s to the low 80s Fahrenheit. However, it's always wise to pack layers, as evenings can be cooler, and occasional rain showers are possible.
Nearby regions
Best Florida Keys, FL vacation rentals with a balcony
9.8 267 reviews
Florida Keys, FL
06/19 – 06/23
$556/nighttotal: $2224 (4 )
Villa Valbuena Azul Escape 2 Kings Key Largo Pickleball Tennis Pool Lagoon
2 4
apartment , Key Largo
This Key Largo apartment is conveniently located just a short drive from John Pennekamp State Park, Pigeon Key, and Windley Key, offering easy access to the area's top attractions. It boasts excellent ratings for location, cleanliness, and overall user experience. The apartment features two bedrooms, making it ideal for families or groups of friends. Guests can enjoy a private beach, free bikes and kayaks, tennis and pickleball courts, a swimming pool, and a fully equipped kitchen.
8.4 5 reviews
Florida Keys, FL
08/22 – 08/23
$311/nightfor 1 night
Swim With Dolphins In The Florida Keys! Free Breakfast & Parking, Marina, Pool!
1 2
apartment , Islamorada, Village of Islands
This Islamorada, Florida aparthotel boasts a central location offering easy access to Indian Key Historic State Park and the History of Diving Museum. The 300-square-foot suite features one bedroom, one bathroom, sleeps four, and includes a kitchen with a refrigerator, microwave, and dishwasher, plus a balcony with partial ocean views, and complimentary continental breakfast, kayaks, paddleboards, and bicycles.
9.1 74 reviews
Florida Keys, FL
07/09 – 07/13
$353/nighttotal: $1412 (4 )
Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar
2 4
apartment , Tavernier
This apartment in Tavernier is a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. It is highly rated for its location, cleanliness, and user experience. The apartment has two bedrooms, two bathrooms, a sofa bed, and a floor area of 830 square feet. It can accommodate up to six guests. Amenities include a private pool, concierge services, barbecue grills, a washing machine, and a smoke-free environment.
9.6 30 reviews
Florida Keys, FL
11/25 – 11/27
$591/nighttotal: $1182 (2 )
Ocean Pointe Condo Ocean View Sleeps 6 In Florida Keys Building 4 Top Floor
2 6
apartment , Tavernier
This Tavernier condo boasts a waterfront location, 0.8 miles from Harry Harris Park and within 3 miles of Mariners Hospital and the Florida Keys Dive Center. The 820-square-foot apartment features two bedrooms, two bathrooms, accommodates seven guests, and includes a fully equipped kitchen, private balcony, access to a swimming pool, jacuzzi, and tennis court.
Best Florida Keys, FL vacation rentals with parking
8.7 510 reviews
Florida Keys, FL
06/20 – 06/27
$216/nighttotal: $1512 (7 )
Matecumbe Resort
1 1
resort , Islamorada, Village of Islands
The Matecumbe Resort is located in Islamorada, just a short drive from Upper Matecumbe Key and close to Sea Oats Beach. This 2-star aparthotel receives very good user ratings for location, cleanliness, and overall experience. The resort offers spacious accommodations with fully equipped kitchens. Guests can enjoy a range of amenities, including a swimming pool, a children's playground, barbecue facilities, bike rentals, and allergy-friendly options.
9.6 4 reviews
Florida Keys, FL
08/04 – 08/07
$508/nighttotal: $1524 (3 )
Imagine In The Keys - Venture Out Unit 073
2 4
cottage , Cudjoe Key
This Cudjoe Key waterfront cottage boasts stunning views and direct access to the water, located 2.4 miles from Florida Keys Beaches and within 6 miles of Upper Sugarloaf Key and Upper Sugarloaf Sound. This 800-square-foot vacation home features two bedrooms, two bathrooms, a private patio, and accommodates up to six guests, offering a swimming pool, jacuzzi, and barbecue grills.
9.8 288 reviews
Florida Keys, FL
07/31 – 08/03
$346/nighttotal: $1038 (3 )
{Privately Owned} This 2 Bedroom Has Everything You Need.\nwith A Fantastic View.
2 2
apartment , Tavernier
This oceanfront condo is located in Tavernier Key, just south of Key Largo, offering easy access to the Florida Keys' natural beauty. The property has received excellent ratings for its location, cleanliness, and overall experience. The apartment has 2 bedrooms and 2 bathrooms, spanning 900 square feet. Guests can enjoy a range of amenities including a swimming pool, jacuzzi, terrace, garden, and parking, as well as access to a beach, marina, and tennis courts.
9.7 127 reviews
Florida Keys, FL
11/25 – 11/27
$486/nighttotal: $972 (2 )
Fish, Dive, Snorkel & Unwind-coral Reefs, Pool, Pickleball & Onsite Bar
2 6
apartment , Tavernier
This waterfront condo in Tavernier offers stunning views and is within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park. With excellent user, location, and cleanliness ratings, this apartment is a great choice for travelers. The apartment has two bedrooms, two bathrooms, and a floor area of 940 square feet, accommodating up to six guests. It features a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a jacuzzi, a terrace or balcony, a garden, a spa, a tennis court, and parking.