Holiday Rentals in Florida Keys, FL

15393 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 15393 accommodations in Florida Keys, FL, here are the 4 best family friendly rentals

Waterfront Villa Bring Your Boat Cabana Club Beach - Florida Keys, FL
9.9 84 reviews

Waterfront Villa Bring Your Boat Cabana Club Beach

apartment, Key Colony Beach
This Key Colony Beach villa, centrally located between Islamorada and Key West, offers easy access (under 1.6 km) to the ocean and Gulf, and is within walking distance of the Cabana Club's beach, pool, and tiki bar.
The 2-bedroom, 2-bathroom property sleeps 5, boasts an open-plan design with water views, a private back patio with grill, fishing equipment, and includes use of ocean kayaks; a 12-metre dock accommodating boats up to 15 metres is also available.
Re-energize At Our Spacious Condo! Get 10% Off Stays Of 7+ Days. Book Now! - Florida Keys, FL
9.7 133 reviews

Re-energize At Our Spacious Condo! Get 10% Off Stays Of 7+ Days. Book Now!

apartment, Key Largo
This two-bedroom apartment in Key Largo is located just a kilometre away from Dolphins Plus Inc and a short walk from the Aquatic Center and Pilot House. The property has been awarded an excellent rating by previous guests.
The apartment can accommodate up to six guests and features a private balcony terrace with stunning water cove views. Guests can enjoy a range of amenities, including a fully equipped kitchen, a washer and dryer, two assigned parking spaces, and access to kayaking, paddleboarding, and jet skiing.
*New* Turtles Pace-private Beach - Florida Keys, FL
10 22 reviews

*New* Turtles Pace-private Beach

apartment, Key Colony Beach
This beachfront Key Colony Beach flat is located near walking and cycling paths, kayak and paddleboard rentals (less than 0.4 km), Sunset Park (0.8 km), and a children's playground (0.4 km).
The two-bedroom, two-bathroom property sleeps four, boasting a fully equipped kitchen with high-end appliances, a private balcony, beach access, and an outdoor tiki hut with a grill; beach chairs, an umbrella, and a cooler are provided.
Holiday Inn Key Largo By Ihg - Florida Keys, FL
8.4 1886 reviews

Holiday Inn Key Largo By Ihg

resort, Key Largo
The Holiday Inn Key Largo, an IHG hotel, is located just 5.1 kilometres from John Pennekamp State Park and a short drive from Dolphin Plus Bayside, making it a convenient base for exploring Key Largo's natural wonders. The hotel has consistently received very good ratings for its location, cleanliness, and overall experience.
The hotel offers a range of amenities to suit all travellers, including a swimming pool, hot tub, spa, fitness centre, and restaurant. Guests can enjoy a variety of water sports, relax on the terrace, or explore the nearby attractions.

Best Florida Keys, FL holiday rentals with a pool

Among the 15393 accommodations in Florida Keys, FL, here are the 4 best rentals with a pool

Charming Cottages, Dockage, Pool, Just Minutes To Key West - Florida Keys, FL
8.6 133 reviews

Charming Cottages, Dockage, Pool, Just Minutes To Key West

cottage, Cudjoe Key
This Summerland Key holiday home is situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, Venture Key, Venture Out Keys, and Out Key, offering easy access to these nearby islands.
The 73 square metre property sleeps four guests in two bedrooms and one bathroom, and includes a fully equipped kitchen, washing machine, barbecue, swimming pool, and parking, plus Wi-Fi access.
Quaint Spanish Colonial  House - Florida Keys, FL
9.9 402 reviews

Quaint Spanish Colonial House

apartment, Leisure City
This three-bedroom apartment is situated in Leisure City, a peaceful neighbourhood in Miami-Dade County, just a short drive from the Redland tropical agricultural area and two marinas. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment provides 167 square metres of living space, accommodating up to 12 guests, making it ideal for families or groups. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, and parking, ensuring a comfortable and enjoyable stay.
New Grenada Suite - Parking Pool & Pets 209 - Florida Keys, FL
9.1 115 reviews

New Grenada Suite - Parking Pool & Pets 209

house, Key West
The NEW Grenada Suite is located in Key West, just a short drive from Duval Street and Mallory Square, offering a peaceful retreat while still being close to the action. The property has consistently received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
This two-bedroom property can accommodate up to six guests, making it ideal for families or groups of friends. The house offers a range of amenities including a private pool, a jacuzzi, a fully equipped kitchen, and a fitness centre, ensuring a comfortable and enjoyable stay.
Turtles Nest 2  Beach, Pool, Restaurant 2bed 2bath - Florida Keys, FL
9.9 158 reviews

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

apartment, Tavernier
This oceanfront condo in Tavernier, Florida, offers direct access to a private beach and marina, with stunning ocean views from the living room, master bedroom, and balcony.
The two-bedroom, two-bathroom apartment sleeps six, boasting a fully equipped kitchen, private balcony overlooking a nature preserve, and access to resort amenities including a heated swimming pool, lighted tennis courts, and a gazebo.

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

Captain Pip's Marina & Hideaway - Florida Keys, FL
8.7 2314 reviews

Captain Pip's Marina & Hideaway

resort, Marathon
Captain Pip's Marina & Hideaway is situated in Marathon, Florida, just 1.4 kilometres from the Seven Mile Bridge and 6.4 kilometres from Sombrero Beach. The resort enjoys a tranquil setting, perfect for a relaxing getaway. It has consistently received very good ratings for its cleanliness, location, and overall experience.
The resort offers a range of amenities and activities for guests to enjoy. The accommodation features a swimming pool, a terrace, a garden, a restaurant, and a bar, as well as a fitness centre. Guests can also rent boats, kayaks, and paddleboards, or take advantage of the on-site fishing, snorkelling, and parasailing opportunities.
Beachside Unit 25 - Paradise Found On Atlantic! - Florida Keys, FL
9.3 89 reviews

Beachside Unit 25 - Paradise Found On Atlantic!

apartment, Key Colony Beach
This apartment is situated in Key Colony Beach, just a 1.6 km walk from both Sunset Park Beach and Coco Plum Beach, offering easy access to the beautiful coastline. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment spans 43 square metres and comfortably accommodates two guests. Amenities include a fully equipped kitchen, a balcony, a swimming pool, a garden, parking, and air conditioning, providing everything you need for a relaxing and enjoyable holiday.
Home Sweet Home Near Malls And Airport And Hwy - Florida Keys, FL
9.4 9 reviews

Home Sweet Home Near Malls And Airport And Hwy

house, Westchester
This two-bedroom property is located in South Miami, just a short drive (around 5 km) from the University of Miami, Miami International Mall, and Miami International Airport. The surrounding area is quiet and residential, offering a peaceful escape from the hustle and bustle of the city centre.
The house spans 65 square metres and comfortably accommodates up to 8 guests. It offers a range of amenities, including free parking, Wi-Fi, a fully equipped kitchen, a terrace and garden, as well as air conditioning.
Island Time - Key Largo! Luxurious 2br/2ba! - Florida Keys, FL
9.0 103 reviews

Island Time - Key Largo! Luxurious 2br/2ba!

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 Tavernier's laid-back charm. The apartment has received excellent user and location ratings and a very good cleanliness rating.
The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, two bathrooms, a washing machine, and a coffee/tea maker. Enjoy relaxing amenities like a TV, internet access, and a terrace/balcony, as well as the convenience of parking and an elevator.

Best Florida Keys, FL holiday rentals with parking

Island Paradise - Florida Keys, FL
9.9 26 reviews

Island Paradise

apartment, Cudjoe Key
This Cudjoe Key island retreat offers a peaceful base, centrally located between Marathon and Key West, providing easy access to both destinations.
The self-catering property sleeps four guests in one bedroom and one bathroom, boasting a swimming pool, Jacuzzi, and all modern conveniences including air conditioning and Wi-Fi.
Dolce Vita Estate  Luxury Private Villa  Events - Florida Keys, FL
9.9 26 reviews

Dolce Vita Estate Luxury Private Villa Events

house, Homestead
This five-bedroom Homestead property, situated in Miami's Redlands, is approximately 16km from the Fruit & Spice Park and Robert Is Here, 32km from Everglades National Park, and 64km from Miami International Airport.
The 5-acre estate boasts a chef's kitchen, three gardens, a heated swimming pool, a fitness centre, parking, and accommodates up to 12 guests, offering fresh eggs from an on-site chicken barn and proximity to Homestead's attractions.
Beachside Unit 26 - Palms, Tiki Huts, Sand & Ocean - Florida Keys, FL
9.6 113 reviews

Beachside Unit 26 - Palms, Tiki Huts, Sand & Ocean

apartment, Key Colony Beach
This apartment is located in Key Colony Beach, just 3km from Sunset Park Beach, Curry Hammock State Park, and San Pablo Catholic Church, offering a convenient base for exploring the area. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment is a 43 square metre property that comfortably sleeps two guests. The apartment has a fully equipped kitchen, a dining area, a terrace, a garden, a swimming pool, and parking, providing everything you need for a relaxing and enjoyable stay.
Dapper Dolphin | Canal View + Breakfast + Pool - Florida Keys, FL
9.9 119 reviews

Dapper Dolphin | Canal View + Breakfast + Pool

apartment, Marathon
This waterfront flat in Marathon, Florida is just 5.6 kilometres from the Florida Keys Aquarium Encounters and 5.8 kilometres from Captain Hook's Marina Dive Center. The property has received excellent ratings for cleanliness, location and user experience.
The one-bedroom flat can accommodate up to four guests and includes a fully equipped kitchen, a private balcony and air conditioning. Guests can enjoy a range of on-site amenities, including a swimming pool, a bar, a fitness centre, a tennis court and parking.
©2026 cozycozy.com