Holiday Rentals in Florida Keys, FL

11639 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Florida Keys, FL holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers 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

Blue Pearl ~ Waterfront Oasis W/ Pool & 70' Dock! - Florida Keys, FL
9.8 20 reviews
Florida Keys, FL
26/12 – 03/01
SG$2242/nighttotal: SG$17936 (8 )

Blue Pearl ~ Waterfront Oasis W/ Pool & 70' 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.
Hawks Cay Resort - Florida Keys, FL
8.0 1408 reviews
Florida Keys, FL
05/08 – 06/08
SG$2035/nightfor 1 night

Hawks Cay Resort

4 13
resort , Duck Key
Hawks Cay Resort is located on Duck Key, just 800 metres from Duck Key Marina and a 27-minute drive from Curry Hammock State Park, offering a peaceful escape in a picturesque setting. The resort consistently receives very good ratings for its location, cleanliness, and overall guest experience.
The resort offers a range of accommodation options, including comfortable rooms and cottages with a Caribbean-style aesthetic. Guests can enjoy a variety of amenities, including multiple swimming pools, a full-service spa, a fitness centre, tennis courts, and a selection of restaurants and bars.
Coconut Cay Resort - Florida Keys, FL
8.4 4055 reviews
Florida Keys, FL
07/07 – 10/07
SG$171/nighttotal: SG$513 (3 )

Coconut Cay Resort

1 2
resort , Marathon
Coconut Cay Resort is situated in Marathon, Florida, a short drive from Sombrero Beach, the Seven Mile Bridge, and the Dolphin Research Center, making it a great base for exploring the area. The resort has received good user ratings, with particularly high marks for its location and cleanliness.
The resort offers a range of amenities, including a swimming pool and sun terrace, a restaurant and bar, and free Wi-Fi and parking. Guests can enjoy a complimentary breakfast, and activities such as kayaking, cycling, fishing, and paddleboarding are available.
Miami Oasis With Luxury Spa & Your Own Helicopter - Florida Keys, FL
9.9 83 reviews
Florida Keys, FL
05/08 – 06/08
SG$1232/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.

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

Beachside Unit 12 - Key Colony - Florida Keys, FL
9.8 156 reviews
Florida Keys, FL
28/09 – 05/10
SG$382/nighttotal: SG$2674 (7 )

Beachside Unit 12 - Key Colony

1 2
apartment , Key Colony Beach
This apartment is situated 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. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The flat is 43 square metres and can accommodate up to four guests. You'll find a well-equipped kitchen, a balcony, and access to a swimming pool, barbecue grills, and a garden.
Cheeca Lodge & Spa - Florida Keys, FL
9.1 3677 reviews
Florida Keys, FL
07/07 – 10/07
SG$387/nighttotal: SG$1161 (3 )

Cheeca Lodge & Spa

1 2
resort , Islamorada, Village of Islands
Cheeca Lodge & Spa is situated on a 27-acre stretch of waterfront in Islamorada, just a 20-minute drive from downtown Key Largo and 13.7 miles from Long Key State Park. The resort has received very good user ratings, with excellent scores for location and cleanliness.
The property features spacious rooms with balconies and resort views. Guests can enjoy a range of amenities, including a 9-hole golf course, spa, fishing pier, swimming pools, fitness centre, tennis courts, and watersports facilities.
Ocean View Condo With Balcony/marina View - Florida Keys, FL
9.2 358 reviews
Florida Keys, FL
04/08 – 07/08
SG$441/nighttotal: SG$1323 (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.
Paradis De La Sirène ~ Piscine ~ Quai ~ Jeux ~ Vue - Florida Keys, FL
10 51 reviews
Florida Keys, FL
26/12 – 03/01
SG$2582/nighttotal: SG$20656 (8 )

Paradis De La Sirène ~ Piscine ~ Quai ~ Jeux ~ Vue

1 10
apartment , Marathon
This waterfront house in Marathon, Florida offers direct access to a 73-foot private dock, perfect for boating and fishing.
The four-bedroom, four-bathroom property sleeps ten guests and boasts a private pool, BBQ grill, games area, and fully equipped kitchen including a wine cooler; a balcony with canal views completes this luxurious getaway.

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 iconic sights. Key West is a must, with its historic Duval Street, the Ernest Hemingway Home and Museum, and Mallory Square for the sunset celebration. Further north, you'll find the Seven Mile Bridge, an engineering marvel offering stunning views, and Bahia Honda State Park, known for its beautiful beaches and historic bridge. John Pennekamp Coral Reef State Park provides incredible snorkelling and diving opportunities.
  • What are the best Airbnb and vacation rentals in Florida Keys, FL?

  • 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 renowned for their vibrant coral reefs, a unique ecosystem teeming with marine life. The annual migration of birds through the Keys is also a spectacular sight. You can witness stunning sunsets, especially from Mallory Square in Key West. The unique ecosystem also includes mangrove forests, providing important habitats for many species.
  • What are the most popular Airbnbs in Florida Keys, FL?

    Among the Airbnbs in Florida Keys, FL, Waterfront Cabana 5, Key Largo Villa - Kawama L1 - 3/3 and Getaway In The Everglades 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 are water bottles to stay hydrated in the Florida heat. Don't forget your camera to capture the stunning scenery, and if you plan on water activities, bring appropriate gear like snorkelling equipment or diving gear.
  • What are the best vacation 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 famous costumed celebration held in October. The Conch Republic Independence Celebration in Key West is another quirky and popular event. Numerous smaller festivals and events celebrating local culture and seafood are held throughout the islands, so checking local listings closer to your travel dates is advisable.
  • 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.
  • 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 mid-range trip, you should budget approximately £150-£300 per day for a couple. This includes accommodation (ranging from budget-friendly motels to luxury resorts), meals at a mix of restaurants and casual eateries, car rental or taxi fares, and entry fees to attractions. Luxury travel will, of course, cost significantly more.
  • 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 fantastic seafood restaurants. Blue Heaven in Key West is a popular choice, known for its Key lime pie. Latitudes, also in Key West, offers stunning waterfront dining. Many smaller, family-run restaurants throughout the islands serve fresh, locally caught seafood. Key lime pie and conch fritters are must-try local specialties.
  • 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 in Key Largo. Explore the mangrove tunnels by kayak or canoe in various locations throughout the Keys. The History of Diving Museum in Islamorada offers a fascinating insight into the history of diving. These offer a more tranquil experience away from the main tourist hubs.
  • What are the best activities for engaging with locals and understanding their culture in the Florida Keys, FL, United States?

    Visiting local markets and interacting with vendors can be a great way to engage with the community. Attending smaller, local festivals or events provides opportunities to meet residents. Spending time in less touristy areas and striking up conversations with people you meet can also offer a glimpse into the local culture. Many restaurants and bars are locally owned, providing authentic interactions.
  • What unique natural landscapes and terrain features can travellers explore in the Florida Keys, FL, United States?

    The Florida Keys offer a unique landscape. The islands themselves are low-lying, with beautiful beaches and mangrove forests. The coral reefs are a major attraction, offering diverse underwater landscapes. The diverse ecosystems include seagrass beds, providing habitats for many marine species. Exploring these environments by boat, kayak, or on foot provides a unique experience.
  • 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 is a good timeframe to explore the Keys properly. A possible itinerary could include three days in Key West, exploring its attractions and enjoying the nightlife. Two days in Islamorada, focusing on water activities and exploring the local shops. One day each in Marathon and Key Largo, with time for relaxation and exploring the natural beauty. This is just a suggestion, and you can adjust it to your interests.

Nearby regions

Best Florida Keys, FL holiday rentals with a balcony

Sunrise Breeze On The Marina [Ocean Pointe 5302] - Florida Keys, FL
9.8 173 reviews
Florida Keys, FL
01/09 – 04/09
SG$387/nighttotal: SG$1161 (3 )

Sunrise Breeze On The Marina [Ocean Pointe 5302]

2 2
apartment , Tavernier
This Tavernier beach apartment is conveniently located within a 10-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's attractions. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The apartment offers 85 square metres of space, comfortably accommodating up to 6 guests in its two bedrooms and two bathrooms. This family-friendly apartment includes a range of amenities such as a swimming pool, Jacuzzi, tennis court, and a garden, ensuring a comfortable and enjoyable stay.
Sea Gulls Oceanfront Condo With Large Heated Oceanfront Pool - Florida Keys, FL
9.3 42 reviews
Florida Keys, FL
27/06 – 04/07
SG$469/nighttotal: SG$3283 (7 )

Sea Gulls Oceanfront Condo With Large Heated Oceanfront Pool

2 2
apartment , Islamorada, Village of Islands
This two-bedroom apartment is located directly on the waterfront in Islamorada, just over 100 kilometres from Miami and within easy reach of numerous bars, restaurants, shops, and a grocery store. This property has received excellent ratings for its location, user experience, and cleanliness.
The 111 square metre apartment can comfortably accommodate up to four guests and features a fully equipped kitchen, a private balcony, and access to a swimming pool, jacuzzi, fitness centre, and garden. Guests can enjoy a range of amenities and activities, including fishing, diving, kayaking, and boat rentals.
Beachside Unit 27 - Key Colony, Beachside Unit 27 - The Beach Is Calling You! - Florida Keys, FL
9.8 133 reviews
Florida Keys, FL
01/09 – 04/09
SG$406/nighttotal: SG$1218 (3 )

Beachside Unit 27 - Key Colony, Beachside Unit 27 - The Beach Is Calling You!

1 2
apartment , Key Colony Beach
This apartment is located on Key Colony Beach, just 1.6km from Sunset Park Beach and Coco Plum Beach, and 3.2km from Curry Hammock State Park. The apartment has received excellent ratings for cleanliness, location and overall experience.
The one-bedroom apartment is 43 square metres and can comfortably accommodate four guests. It offers a range of amenities including a fully equipped kitchen, a balcony, air conditioning, a swimming pool, and free parking.
Ocean Front Breeze In Paradise - Florida Keys, FL
10 3 reviews
Florida Keys, FL
27/06 – 04/07
SG$251/nighttotal: SG$1757 (7 )

Ocean Front Breeze In Paradise

1 2
apartment , Marathon
Ocean Front Breeze in Paradise, a self-catering apartment in Marathon, Florida, offers stunning ocean views and is a short walk (less than 1 km) from Florida Keys Aquarium Encounters, with Captain Hook's Marina Dive Center (1.8 km) and A Deep Blue Dive Center (2.9 km) also nearby.
This 425 square metre flat boasts one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, Wi-Fi, a balcony, a swimming pool, and laundry service.

Best Florida Keys, FL holiday rentals with parking

P41 - Beach Front Condo With 2 Bedrooms, 2 Bath, Pool And Tennis Courts! - Florida Keys, FL
9.5 40 reviews
Florida Keys, FL
26/06 – 06/07
SG$411/nighttotal: SG$4110 (10 )

P41 - Beach Front Condo With 2 Bedrooms, 2 Bath, Pool And Tennis Courts!

2 6
apartment , Marathon
This two-bedroom apartment is situated directly on the beach in Marathon, just 3 kilometres from Sunset Park Beach and Captain Hooks Marina and Dive Center, with Curry Hammock State Park and Coco Plum Beach within a 1 kilometre walk. This property has received excellent reviews for its location, cleanliness, and overall experience.
The apartment offers a comfortable living space for up to 6 guests, with two bathrooms and a fully equipped kitchen. Enjoy a relaxing swim in the private pool, barbecue on the shared grills, and take advantage of the balcony, garden, and free Wi-Fi.
Penthouse Apartment Sunsets In Key Largo, Kawama Yacht Club Tower - Florida Keys, FL
9.9 193 reviews
Florida Keys, FL
28/09 – 05/10
SG$339/nighttotal: SG$2373 (7 )

Penthouse Apartment Sunsets In Key Largo, Kawama Yacht Club Tower

2 2
apartment , Key Largo
This apartment is situated on the beach in Key Largo, within 2 miles of Baker's Cay Resort Beach, Jimmy Johnson's Big Chill, and Jacob's Aquatic Center. It has received excellent ratings for location, cleanliness, and user experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, a garden, a tennis court, and parking.
Oceanfront, 2 Bedroom Unit At Ocean Pointe Condominium - Florida Keys, FL
9.7 92 reviews
Florida Keys, FL
27/06 – 04/07
SG$475/nighttotal: SG$3325 (7 )

Oceanfront, 2 Bedroom Unit At Ocean Pointe Condominium

2 2
apartment , Tavernier
This waterfront apartment in Tavernier is ideally located within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's main attractions. The property consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The two-bedroom apartment spans 79 square metres and comfortably accommodates up to four guests. Enjoy a range of amenities including a private pool, fenced yard, and a fully equipped kitchen, as well as access to a shared swimming pool, jacuzzi, garden, tennis court, and parking.
Beachside Unit 01 - Key Colony, Beachside Unit 01 - Private Atlantic Beach & Pool - Florida Keys, FL
9.6 113 reviews
Florida Keys, FL
01/09 – 04/09
SG$406/nighttotal: SG$1218 (3 )

Beachside Unit 01 - Key Colony, Beachside Unit 01 - Private Atlantic Beach & Pool

1 2
apartment , Key Colony Beach
This apartment is located in Key Colony Beach, just a 3-kilometre drive from Curry Hammock State Park and within a 1.6-kilometre walk of Sunset Park Beach and Coco Plum Beach. The apartment has received excellent user ratings for its cleanliness, location, and overall experience.
The apartment is a 43 square metre, one-bedroom property that can comfortably accommodate two guests. Enjoy the private pool, the fully equipped kitchen, and the terrace, where you can relax and enjoy the beautiful surroundings.
©2026 cozycozy.com