Compare Vacation Rentals & Airbnb in Florida Keys

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Florida Keys vacation rentals
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15393 Rentals and Airbnb in Florida Keys

Best family friendly Florida Keys vacation rentals

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

Waterfront Villa Bring Your Boat Cabana Club Beach - Florida Keys
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.
Islander Resort - Florida Keys
9.1 3918 reviews

Islander Resort

resort, Islamorada, Village of Islands
Islander Resort is situated directly on the beach in Islamorada, offering easy access to the beautiful waters of the Florida Keys and the area's attractions. The resort has received very good ratings for its overall experience, with excellent marks for its location and cleanliness.
The resort provides spacious rooms with private porches or lanais, perfect for enjoying the tropical ambiance. Guests can enjoy a range of amenities including swimming pools, a bar and restaurant, a spa, a fitness centre, and a concierge service.
*New Modern*3/2duplex/37' Dock/cabana/kayaks/bikes - Florida Keys
9.8 137 reviews

*New Modern*3/2duplex/37' Dock/cabana/kayaks/bikes

house, Key Colony Beach
This apartment is located just a 2-minute walk from Sunset Park in Key Colony Beach, offering easy access to the Cabana Club and a canal leading to both the Ocean and the Gulf. It has consistently received excellent ratings for location, cleanliness, and user experience.
The 157 square metre apartment comfortably sleeps up to 8 guests in 3 bedrooms and 2 bathrooms. It features a spacious backyard with a multi-game table, bikes, kayaks, and a 6-burner grill, as well as a fully equipped kitchen, air conditioning, a swimming pool, and direct canal access with 11.4 metres of dockage.
Marina Del Mar Resort And Marina - Florida Keys
8.6 1993 reviews

Marina Del Mar Resort And Marina

resort, Key Largo
Marina Del Mar Resort And Marina enjoys a central Key Largo location, close to the marina, shops, and restaurants, and approximately 63 kilometres from Homestead Miami Speedway.
This Key Largo hotel offers guest rooms and studios with kitchenettes, a swimming pool, jacuzzi, tennis court, on-site restaurant (Skippers Dockside), marina with boat trips to John Pennekamp Coral Reef State Park, and free Wi-Fi and parking.

Best Florida Keys vacation rentals with a pool

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

Snowbird-friendly Sound View Condo With Open Layout, Patio, W/d, & Ac - Florida Keys
9.4 8 reviews

Snowbird-friendly Sound View Condo With Open Layout, Patio, W/d, & Ac

apartment, Marathon
This Marathon Shores condominium is situated near Sombrero Beach and Curry Hammock State Park, with Marathon Air Museum and Crane Point Museum and Nature Center also in close proximity.
This 79 square metre flat offers accommodation for four guests with one bedroom and two bathrooms, featuring a full kitchen, air conditioning, swimming pool, and parking, with jet skiing, kayaking, and cycling available nearby.
Swaying Palms Spacious Suite [Ocean Pointe 3201] - Florida Keys
9.9 117 reviews

Swaying Palms Spacious Suite [Ocean Pointe 3201]

apartment, Tavernier
This Tavernier waterfront apartment, a short 1km stroll from Harry Harris Park and within 5km of Mariners Hospital and Pigeon Key, offers stunning views.
The two-bedroom, two-bathroom condo sleeps four, boasting a fully equipped kitchen, free Wi-Fi, a swimming pool, Jacuzzi, tennis court, and private terrace – perfect for families seeking a relaxing Tavernier getaway.
Gorgeous Waterfront Townhome - Florida Keys
9.6 107 reviews

Gorgeous Waterfront Townhome

apartment, Key Largo
This yacht is located in Key Largo, just a short distance from John Pennekamp Coral Reef State Park, offering easy access to both freshwater and saltwater activities. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The yacht has two bedrooms and two bathrooms, providing comfortable accommodation for a small family or group of friends. It includes a range of amenities such as a swimming pool, a garden, parking, and internet access, ensuring a relaxing and enjoyable stay.
Airy Top Floor Blue Heron Suite; Ocean Pointe 3407 - Florida Keys
9.8 120 reviews

Airy Top Floor Blue Heron Suite; Ocean Pointe 3407

apartment, Tavernier
This waterfront property in Tavernier is located within a short walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the area's natural beauty. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The spacious two-bedroom flat, covering 85 square metres, comfortably accommodates up to six guests. Enjoy a range of amenities including a fully equipped kitchen, a swimming pool, a Jacuzzi, a tennis court, and a spa, making it ideal for a relaxing and enjoyable stay.

Frequently Asked Questions about vacation rentals in Florida Keys

  • What are the must-see sights in the Florida Keys, 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 Key West Butterfly and Nature Conservatory. Further up the Keys, you'll find the Seven Mile Bridge, a breathtaking engineering marvel, and Bahia Honda State Park, boasting pristine beaches and excellent snorkeling. Don't miss the John Pennekamp Coral Reef State Park, a great place for diving and exploring the only living coral reef in the continental United States.
  • What are the best Airbnb and vacation rentals in Florida Keys?

  • 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, United States?

    Absolutely! The Florida Keys are known for their vibrant coral reefs, a unique ecosystem teeming with marine life. The area also experiences stunning sunsets, often cited as some of the best in the world. Birdwatching is excellent, with many species migrating through or residing in the Keys. The unique geography and climate also contribute to the diverse plant life found throughout the islands.
  • What are the most popular Airbnbs in Florida Keys?

  • 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, United States?

    Pack light clothing, swimwear, sunscreen (high SPF!), sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially if you plan on exploring the more natural areas. A reusable water bottle is crucial, as staying hydrated is important in the Florida Keys' climate. Consider bringing a waterproof bag for electronics and valuables if you plan on watersports.
  • What are the best vacation rentals with a pool in Florida Keys?

  • 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, United States?

    The Florida Keys host several events throughout the year. Key West's Fantasy Fest is a renowned costumed celebration in October. The annual Hemingway Days celebration in July honors the famous author's legacy. Numerous smaller festivals and events related to fishing, music, and art take place throughout the year in various Keys communities.
  • What are the best rentals for families and kids in Florida Keys?

  • 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, United States, and what are the must-try specialties?

    The Florida Keys boast a diverse culinary scene. Key West has numerous excellent restaurants. Try the Blue Heaven for its casual atmosphere and Caribbean-inspired dishes. Latitudes, located at the Cheeca Lodge & Spa in Islamorada, offers stunning sunset views and fresh seafood. Many restaurants feature fresh, locally caught seafood, conch fritters, and Key lime pie—a must-try dessert.
  • What are the best rentals or Airbnbs with a jacuzzi in Florida Keys?

    The best vacation rentals or Airbnb with a jacuzzi in Florida Keys are Leaward Isle Island Retreat, Marlin Bay Resort & Marina Managed By Elite Alliance Hospitality and Key West Villas.

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

    Beyond the well-known spots, consider exploring the smaller islands and quieter beaches. The National Key Deer Refuge provides a chance to see these endangered deer in their natural habitat. The History of Diving Museum in Islamorada offers a fascinating look at diving's past. Exploring the backcountry by kayak or paddleboard reveals hidden coves and mangroves, offering a different perspective of the Keys.
  • What are the best activities for engaging with locals and understanding their culture in the Florida Keys, United States?

    Visiting local markets, like the Key West Green Market, provides a chance to interact with locals and sample local produce. Attending community events and festivals offers insight into local traditions. Striking up conversations with bartenders and staff at smaller, locally-owned establishments can lead to interesting interactions and local insights. Consider taking a guided tour focused on the history and culture of the Keys.
  • What unique natural landscapes and terrain features can travelers explore in the Florida Keys, United States?

    The Florida Keys' unique landscape is defined by its low-lying islands, mangrove forests, and the only living coral reef in the continental US. Exploring the backcountry waterways by boat or kayak reveals hidden mangrove tunnels and diverse birdlife. The beaches vary from the white sands of Bahia Honda State Park to the more rugged shores of other islands. The diverse ecosystems offer a variety of landscapes to explore.
  • How many days are ideal for visiting the Florida Keys, United States, and what are some itinerary suggestions?

    Seven to ten days is ideal to explore the Keys thoroughly. A possible itinerary could involve three days in Key West, two in Islamorada, and two exploring the Upper Keys, including Marathon and Bahia Honda State Park. This allows for relaxation, exploration, and enjoying diverse activities. Adjust the itinerary based on your interests and preferred pace.

Nearby regions

Best Florida Keys vacation rentals with a balcony

Sea Glass & Sunshine 2207 Ocean Pointe - Florida Keys
No reviews

Sea Glass & Sunshine 2207 Ocean Pointe

apartment, Tavernier
This Florida Keys flat offers a prime location in Tavernier, situated midway between Key Largo and Islamorada, placing you conveniently close to the US reef system for diving and snorkeling, with the John Pennekamp Coral Reef State Park just a short drive away.
This recently renovated two-bedroom, two-bathroom condo spans 77 square meters, accommodating up to five guests with a king bed, two twin beds, and a sofa bed, and features onsite resort amenities including a swimming pool, hot tub, sandy beach, tennis courts, and marina access for boats up to 28 feet.
Spring & Summer Dates Available Licensed Rental Vr #25-0235  No Boats - Florida Keys
10 62 reviews

Spring & Summer Dates Available Licensed Rental Vr #25-0235 No Boats

apartment, Islamorada, Village of Islands
This family-friendly apartment is located on the beach in Islamorada, within a short distance of Islamorada County Park, Founders Park, and the Florida Keys Dive Center. It has received excellent user ratings, making it a popular choice for travellers.
The apartment is spacious, covering 74 square metres and comfortably accommodating up to six guests. It comes with a range of amenities, including a swimming pool, a tennis court, and a fitness centre, ensuring a comfortable and enjoyable stay.
Welcome To Paradise! - Florida Keys
9.6 91 reviews

Welcome To Paradise!

apartment, Key Largo
This one-bedroom apartment is situated in the gated oceanfront community of Kawama Yacht Club in Key Largo, offering direct access to the ocean and a short walk to the beach. The apartment has received excellent user ratings, making it a popular choice for travellers.
The 84 square metre apartment can accommodate up to 4 guests and features a modern kitchen, a spacious living area with a convertible sofa bed and daybed, and a private balcony overlooking a nature preserve. Guests can enjoy a range of amenities, including three heated swimming pools, a saltwater lagoon with a sand beach, tennis and pickleball courts, a fishing jetty, and complimentary boat launch facilities.
Waterfront Islamorada Condo  Heated Pool, Marina & Deeded Boat Slip - Florida Keys
10 69 reviews

Waterfront Islamorada Condo Heated Pool, Marina & Deeded Boat Slip

apartment, Islamorada, Village of Islands
This Islamorada condominium is situated at mile marker 88.5, offering convenient access to Robbie's Marina and the Theater of the Sea, with Miami located 108 kilometres to the north.
This family-friendly apartment, measuring 88 square metres and accommodating up to six guests, features two bedrooms and two bathrooms, a fully equipped kitchen with granite countertops, a private balcony with pool views, direct access to a deeded boat slip (#49), and resort-style amenities including a heated swimming pool and pickleball courts.

Best Florida Keys vacation rentals with parking

Marina And Ocean View, 2 Bed, 2 Bath End Unit 4201 - Florida Keys
10 40 reviews

Marina And Ocean View, 2 Bed, 2 Bath End Unit 4201

apartment, Tavernier
This Ocean Pointe Suites condo in Tavernier, Florida boasts stunning marina and ocean views, and is situated near Anne's Beach in Islamorada, the precise distance unstated.
The 916 sq ft (85 sq m) two-bedroom, two-bathroom apartment sleeps five, features a private balcony, full resort access including a swimming pool and jacuzzi, and offers 24-hour self check-in.
Dock, Quick Access, Cabana Club, Fishing, Spacious - Florida Keys
10 102 reviews

Dock, Quick Access, Cabana Club, Fishing, Spacious

apartment, Key Colony Beach
This Key Colony Beach waterfront property is situated within 3.2km of Sunset Park Beach, Marathon Visitor Centre, and Curry Hammock State Park, offering stunning views and easy access to local attractions.
This three-bedroom, three-bathroom holiday home boasts 193 square metres of living space, a private fenced yard, swimming pool, Jacuzzi, and spa, plus free Wi-Fi and a fully equipped kitchen; perfect for families or groups seeking a relaxing Key Colony Beach getaway.
Deluxe Oceanfront 1/1 Sleeps 4. Cafe & Pool Bar. - Florida Keys
9.7 131 reviews

Deluxe Oceanfront 1/1 Sleeps 4. Cafe & Pool Bar.

apartment, Tavernier
This Tavernier apartment is located just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, both offering a relaxed beach atmosphere, and is within 5 kilometres of Mariners Hospital and Florida Keys Dive Center. It has received excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom apartment spans 60 square metres and comfortably accommodates up to four guests. It offers a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and a garden, ensuring a relaxing and enjoyable stay.
Reel Key Largo Escape Ocean Pointe 5209 - Florida Keys
9.8 11 reviews

Reel Key Largo Escape Ocean Pointe 5209

house, Tavernier
Ocean Pointe 5209, Key Largo, offers a two-bedroom house in Tavernier, a 2.4km walk from Harry Harris Park Beach and 4.5km from Pigeon Key.
This 77 square metre property sleeps six, boasting a private patio with ocean views, a swimming pool, jacuzzi, and fully equipped kitchen including a dishwasher; free Wi-Fi and on-site parking are also provided.
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