Holiday Rentals in Florida Keys, FL

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Florida Keys, FL holiday rentals
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11639 Holiday Rentals and Airbnb in Florida Keys, FL

Best family friendly Florida Keys, FL holiday rentals

Among the 11639 accommodations in Florida Keys, FL, here are the 4 best family friendly rentals

Two Authentic Conch Houses With Private Beach On Fl Bay - Florida Keys, FL
10 50 reviews
Florida Keys, FL
26/12 – 03/01
NZ$4869/nighttotal: NZ$38952 (8 )

Two Authentic Conch Houses With Private Beach On Fl Bay

3 10
apartment , Tavernier
This two-Conch-house holiday let in Tavernier, Florida Keys, offers direct access to a private beach on Florida Bay and is situated between Key Largo and Islamorada, a short distance from John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park.
Spanning 111 square metres, this pet-friendly accommodation comfortably houses up to 10 guests with three bedrooms and three bathrooms, featuring a Jacuzzi with sunset views, a private beach with water toys, and dock access for boats.
Florida Keys Retreat /Game Room / Boat Parking - Florida Keys, FL
9.6 49 reviews
Florida Keys, FL
28/09 – 05/10
NZ$376/nighttotal: NZ$2632 (7 )

Florida Keys Retreat /Game Room / Boat Parking

1 2
apartment , Marathon
This Marathon Airbnb, minutes from Sombrero Beach and within walking distance (approximately 0.8km) of local restaurants, shops, and the marina, offers a convenient location for exploring the Florida Keys.
The two-bedroom, two-bathroom house sleeps six, includes a dedicated games room with a Nintendo Switch and fishing rods, and allows parking for up to three vehicles plus a boat trailer (maximum 7.6m).
35' Seawall Sparkling , 30min From Keywest, Wifi, Bbq Grill, Pool - Florida Keys, FL
9.8 132 reviews
Florida Keys, FL
26/06 – 06/07
NZ$713/nighttotal: NZ$7130 (10 )

35' Seawall Sparkling , 30min From Keywest, Wifi, Bbq Grill, Pool

2 6
cottage , Cudjoe Key
This 35' Seawall Sparkling mobile home is situated in Summerland Key, just a short distance from the beach and within walking distance of the amenities at Venture Out Residential Condominium. It has received excellent user ratings, making it a popular choice for travellers. This two-bedroom, two-bathroom home offers 79 square metres of space and can comfortably accommodate up to six guests. The home features a modern kitchen with a dishwasher, a spacious living area with a pull-out queen sleeper sofa, and a private porch overlooking the water, perfect for relaxing and enjoying the views.
Ocean View Condo With Balcony/marina View - Florida Keys, FL
9.2 358 reviews
Florida Keys, FL
04/08 – 07/08
NZ$590/nighttotal: NZ$1770 (3 )

Ocean View Condo With Balcony/marina View

2 4
apartment , Tavernier
This two-bedroom apartment in Tavernier is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful sands and turquoise waters of the Florida Keys. It has received excellent ratings for location, cleanliness, and user experience.
The 80 square metre property can accommodate up to six guests and features a fully equipped kitchen, a private balcony, a swimming pool, a Jacuzzi, a sauna, a tennis court, and free parking. Guests can also enjoy the outdoor barbecue grills and relax in the spa tub after a day exploring the Keys.

Best Florida Keys, FL holiday rentals with a pool

Among the 11639 accommodations in Florida Keys, FL, here are the 4 best rentals with a pool

Lovely 1/1 Condo In Cocoplum W Dockage,pool & Ramp - Florida Keys, FL
9.7 14 reviews
Florida Keys, FL
27/06 – 04/07
NZ$328/nighttotal: NZ$2296 (7 )

Lovely 1/1 Condo In Cocoplum W Dockage,pool & Ramp

1 2
apartment , Marathon
This Coco Plum condo in Marathon offers a peaceful setting near the canal, providing easy access to water activities.
The one-bedroom apartment, sleeping two guests, boasts a fully equipped kitchen, private patio with pool and garden views, and access to an on-site pool and boat ramp; boat trailer parking is also available.
Work Remote, Or Not At All, In Paradise At This Cozy, Beachy Condo! - Florida Keys, FL
9.6 90 reviews
Florida Keys, FL
27/06 – 04/07
NZ$577/nighttotal: NZ$4039 (7 )

Work Remote, Or Not At All, In Paradise At This Cozy, Beachy Condo!

2 2
apartment , Islamorada, Village of Islands
This Islamorada seaside apartment, near Old Road Gallery and Founders Park (within 3km), offers stunning ocean views and easy beach access.
The 79 square metre property sleeps six, boasting two bedrooms, two bathrooms, a fully equipped kitchen, free Wi-Fi, a pool, jacuzzi, and tennis court, plus barbecue facilities and limited housekeeping.
Huge Oct Savings!  Sea-esta! Condo, Beach, Pool, Key Colony Beach! - Florida Keys, FL
9.9 63 reviews
Florida Keys, FL
27/06 – 04/07
NZ$435/nighttotal: NZ$3045 (7 )

Huge Oct Savings! Sea-esta! Condo, Beach, Pool, Key Colony Beach!

2 2
apartment , Key Colony Beach
This apartment is located in Key Colony Beach, just a short walk from Sunset Park Beach and Coco Plum Beach, and within 3km of Curry Hammock State Park and San Pablo Catholic Church, offering a peaceful retreat in a tranquil setting. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This 91 square metre property features two bedrooms and two bathrooms, comfortably accommodating up to four guests. The apartment offers a range of amenities including a fully equipped kitchen, a balcony, a swimming pool, a garden, a tennis court, and parking, ensuring a comfortable and enjoyable stay.
Casa Seagulls - Florida Keys, FL
9.8 45 reviews
Florida Keys, FL
27/06 – 04/07
NZ$527/nighttotal: NZ$3689 (7 )

Casa Seagulls

2 2
apartment , Islamorada, Village of Islands
This two-bedroom apartment is situated in Islamorada, directly overlooking the Atlantic Ocean, within walking distance of fishing, snorkeling, diving, and kayak/paddleboard rentals. Local charters for these activities are about 1.6 kilometres away. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This comfortable property can sleep up to four adults and features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a swimming pool, a garden, a fitness centre, and parking. Guests can enjoy stunning ocean views from the spacious porch, relax by the pool, or barbecue on the beach.

Frequently asked questions about holiday 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 sights. Key West is a must, with its iconic Southernmost Point Buoy, Ernest Hemingway Home and Museum, and the beautiful Mallory Square sunset celebration. Further up the Keys, you'll find the John Pennekamp Coral Reef State Park, perfect for snorkelling and diving, and the Seven Mile Bridge, an engineering marvel offering stunning views. Don't miss the historic lighthouse at Key West and the charming shops and restaurants throughout the islands.
  • What are the best Airbnb and holiday rentals in Florida Keys, FL?

    Marlin Bay Resort & Marina Managed By Elite Alliance Hospitality, Leaward Isle Island Retreat and Relaxed Boho Vibes & Views [ Ocean Pointe 2315] are the most popular Airbnb and holiday rentals in Florida Keys, FL among travellers.

  • What are vacation rentals like in Florida?

    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 Florida Keys are known for their vibrant coral reefs, a unique ecosystem teeming with marine life. The annual migration of birds through the Keys is another spectacular natural event. You can also witness stunning sunsets, particularly from Mallory Square in Key West.
  • What are the most popular Airbnbs in Florida Keys, FL?

    Among the Airbnbs in Florida Keys, FL, Relaxed Boho Vibes & Views [ Ocean Pointe 2315], Waterfront Cabana 6 and Key Largo Villa - Kawama L1 - 3\/3 are the most popular ones.

  • 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 is a reusable water bottle to stay hydrated in the Florida heat. Don't forget your camera to capture the stunning scenery!
  • What are the best holiday rentals with a pool in Florida Keys, FL?

  • What are the top destinations in Florida?

    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 several 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.
  • What are the best rentals for families and kids in Florida Keys, FL?

  • What dishes should I try in Florida?

    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.
  • 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 a diverse culinary scene. For fresh seafood, try the Blue Heaven in Key West, known for its laid-back atmosphere and delicious Key lime pie. Another popular choice is Louie's Backyard, also in Key West, offering stunning waterfront views. Key lime pie, conch fritters, and stone crab claws are local must-try dishes.
  • What are the best rentals or Airbnbs with a jacuzzi in Florida Keys, FL?

  • What are some less-famous attractions in the Florida Keys, FL, United States that are worth a visit?

    Consider visiting the African Queen, a historic boat featured in a Humphrey Bogart film, in Key Largo. The History of Diving Museum in Islamorada is another hidden gem. Explore the various smaller, quieter beaches along the Overseas Highway for a more secluded experience.
  • What are the best activities for engaging with locals and understanding their culture in the Florida Keys, FL, United States?

    Chatting with locals at smaller, family-run restaurants and bars is a great way to learn about the Keys' culture. Attend local events and festivals to experience the community spirit. Visiting local markets and interacting with artisans can also provide insights into the local way of life.
  • What unique natural landscapes and terrain features can travellers explore in the Florida Keys, FL, United States?

    The Florida Keys' unique landscape is defined by its coral reefs, mangrove forests, and the Overseas Highway, a scenic road spanning the islands. Explore the various beaches, each with its own character, and take a boat trip to see the diverse marine life.
  • How many days are ideal for a trip to the Florida Keys, FL, United States, and what are some itinerary suggestions?

    Seven to ten days allows for a good exploration of the Keys. A possible itinerary could include three days in Key West, two in Islamorada, and two in Key Largo, allowing time for relaxation and activities. Adjust based on your interests and preferred pace.

Nearby regions

Best Florida Keys, FL holiday rentals with a balcony

Blue Pearl ~ Waterfront Oasis W/ Pool & Dock! - Florida Keys, FL
9.8 20 reviews
Florida Keys, FL
26/12 – 03/01
NZ$2999/nighttotal: NZ$23992 (8 )

Blue Pearl ~ Waterfront Oasis W/ Pool & Dock!

4 10
house , Marathon
This beachfront property in Marathon, Florida, is a short walk from Sunset Park Beach and Coco Plum Beach, and within 1.6 km of Curry Hammock State Park and the Marathon Visitor Centre.
This 186 square metre house boasts four bedrooms, three bathrooms, sleeps ten guests, and features a private pool, fully equipped kitchen, and free Wi-Fi, plus optional housekeeping.
Doubletree By Hilton Grand Key Resort - Florida Keys, FL
8.3 1662 reviews
Florida Keys, FL
05/08 – 06/08
NZ$3398/nightfor 1 night

Doubletree By Hilton Grand Key Resort

6 13
resort , Key West
The Doubletree By Hilton Grand Key Resort offers a convenient base on the outskirts of historic Old Town Key West, just a 2-minute drive from Key West International Airport, Duval Street, and Old Town, with a complimentary shuttle service to these key areas and Smathers Beach.
This resort features a swimming pool with a poolside tiki bar, on-site dining at Palm Haven Restaurant and Sanctuary Lounge, and guest rooms equipped with flat-screen TVs and mini-refrigerators, with select rooms offering balconies and sofa beds, alongside bicycle rentals and a fitness centre.
Island Oasis ~ Your Paradise Awaits In Venture Out Resort! - Florida Keys, FL
9.6 14 reviews
Florida Keys, FL
04/08 – 07/08
NZ$907/nighttotal: NZ$2721 (3 )

Island Oasis ~ Your Paradise Awaits In Venture Out Resort!

2 4
cottage , Cudjoe Key
Island Oasis ~ Your Paradise Awaits In Venture Out Resort! is a waterfront cottage in Cudjoe Key, Florida, conveniently located within a 2.4-kilometre radius of Florida Keys Beaches and a 15-minute walk from Venture Out Keys, Venture Key, and Out Key.
This two-bedroom, two-bathroom holiday home sleeps six guests and boasts a fully equipped kitchen, private balcony, swimming pool, tennis court, and access to barbecue grills; enjoying stunning views and easy water access.
Manatee Bay: Escape To This 2br Duck Key Villa, Private Patio, Dip Pool & Easy Access To Marathon - Florida Keys, FL
9.4 81 reviews
Florida Keys, FL
04/08 – 07/08
NZ$640/nighttotal: NZ$1920 (3 )

Manatee Bay: Escape To This 2br Duck Key Villa, Private Patio, Dip Pool & Easy Access To Marathon

2 4
apartment , Duck Key
This charming house is situated in Marathon, Florida, just 5 kilometers from Little Conch Key, Curry Hammock State Park, and Walkers Island, offering a peaceful retreat close to popular attractions. It has received excellent ratings for location, cleanliness, and user experience.
The property spans 84 square meters and comfortably accommodates up to 6 guests in its two bedrooms and two bathrooms. The house features a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking, as well as internet access, making it ideal for a relaxing and enjoyable stay.

Best Florida Keys, FL holiday rentals with parking

Beachside Unit 07 - Key Colony - Florida Keys, FL
9.7 96 reviews
Florida Keys, FL
27/06 – 04/07
NZ$534/nighttotal: NZ$3738 (7 )

Beachside Unit 07 - Key Colony

1 2
apartment , Key Colony Beach
This apartment is situated in Key Colony Beach, just a 3 km walk from Sunset Park Beach and Coco Plum Beach, and within 3 km of Curry Hammock State Park. The property has received excellent ratings for location, cleanliness, and overall user experience.
The flat is a 43 square metre, one-bedroom home with a capacity for four guests. Amenities include a fully equipped kitchen, a balcony, a swimming pool, barbecue grills, and parking.
Sweet Retreat! 4 Bedroom 2.5 Baths Sombrero Beach W Pool Jacuzzi, 37` Dock 2 Kayaks 2 Paddleboards Included - Florida Keys, FL
9.4 64 reviews
Florida Keys, FL
26/12 – 03/01
NZ$2264/nighttotal: NZ$18112 (8 )

Sweet Retreat! 4 Bedroom 2.5 Baths Sombrero Beach W Pool Jacuzzi, 37` Dock 2 Kayaks 2 Paddleboards Included

4 10
apartment , Marathon
This waterfront property is situated in Marathon, Florida, just 1 kilometre from the Florida Keys Country Club and 4.7 kilometres from Sombrero Beach.
This four-bedroom house, offering space for up to 10 guests, features a private pool, spa tub, barbecue grills, and a fully equipped kitchen with a dishwasher, fridge, freezer and microwave oven.
Starfish Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated! - Florida Keys, FL
9.8 75 reviews
Florida Keys, FL
04/08 – 07/08
NZ$517/nighttotal: NZ$1551 (3 )

Starfish Cottage - Sleeps 4 - Escape The Cold; Our Pool Is Heated!

1 4
cottage , Cudjoe Key
The New Hidden Hammock Resort - Pink Cottage Unit #3, a seaside cottage in Cudjoe Key, Florida, is located less than 1.6km from Florida Keys Beaches and Crab Key, and within 9.6km of the Big Pine Key Flea Market and National Key Deer Refuge Visitor Centre.
This 51-square-metre self-catering property features one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen, private balcony, free Wi-Fi, and access to a swimming pool and garden.
Miami Oasis With Luxury Spa & Your Own Helicopter - Florida Keys, FL
9.9 83 reviews
Florida Keys, FL
05/08 – 06/08
NZ$1648/nightfor 1 night

Miami Oasis With Luxury Spa & Your Own Helicopter

1 13
house , Cutler Bay
This six-bedroom Spanish-style villa is located in South Miami, approximately 16 kilometres from Miami Zoo and Southland Mall.
The property, sleeping up to 16 guests, boasts a heated pool, jacuzzi, sauna, fitness centre, and ample parking, plus Netflix-connected TVs and high-speed Wi-Fi throughout.
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