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Florida Keys, FL short term rentals
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Best Short term and Weekly rentals in Florida Keys, FL

Best family friendly Florida Keys, FL Short term rentals

Among the 11096 accommodations in Florida Keys, FL, here are the 4 best family friendly rentals

Cozy Rooms Close To Florida Keys And More - Florida Keys, FL
8.6 12 reviews

Cozy Rooms Close To Florida Keys And More

B&B, Florida City
This Florida City guesthouse is conveniently located near Homestead Miami Speedway (5.7 miles), Fruit & Spice Park (7.5 miles), and offers easy access to the Florida Keys Overseas Highway.
The one-bedroom, one-bathroom unit features a fully equipped kitchen with a fridge, microwave, and dishwasher, free Wi-Fi, private parking, and a shared lounge area; pets are welcome.
Palm Cottage - Sleeps 4  Summer Fun ..Lobster Season. - Florida Keys, FL
9.8 56 reviews

Palm Cottage - Sleeps 4 Summer Fun ..Lobster Season.

cottage, Cudjoe Key
Palm Cottage, a pet-friendly Summerland Key vacation home, is located less than a mile from Florida Keys Beaches, Crab Key, and Pye Key, offering easy access to swimming, sunbathing, and exploring the natural beauty of the Keys.
This 480-square-foot cottage features two bedrooms, one bathroom, and accommodates four guests, providing a private patio, fully equipped kitchen, free Wi-Fi, and access to a shared pool and barbecue grills.
Keeper Cottage 3 Br Canal-front, Private, Xl Porch - Florida Keys, FL
9.7 100 reviews

Keeper Cottage 3 Br Canal-front, Private, Xl Porch

apartment, Key Colony Beach
This canal-front cottage is located in Key Colony Beach, within walking distance of restaurants and Sunset Park, and a short drive from the Cabana Club. It boasts excellent user, location, and cleanliness ratings, making it a great choice for your vacation.
The 1,350-square-foot home comfortably sleeps six guests in its three bedrooms and two bathrooms. Guests enjoy a fully equipped kitchen, a large screened porch, a private backyard patio, and access to a private dock, a kayak, beach chairs, fishing rods, and more.
Amazing Sunset & Water Views! Pool & Boat Slip! - Florida Keys, FL
9.9 97 reviews

Amazing Sunset & Water Views! Pool & Boat Slip!

apartment, Marathon
Blue Turtle Villa, a 5-bedroom luxury house rental in Marathon's Tides at Vaca Cut community, offers easy walking access to Florida Keys Aquarium Encounters and nearby restaurants, with Sombrero Beach and Bahia Honda State Park a short drive away.
This 2290-square-foot waterfront villa sleeps 12 guests and boasts a private heated pool (fee applies), private boat slip (up to 35 feet), ample on-site amenities including paddle boards, kayaks, and a gas grill, plus a fully equipped kitchen with high-end appliances and an electric car charger.

Best Florida Keys, FL lodging with a balcony

Oceanside, Fee-less Pet, With Kayaks - 60 Ft Dock - Florida Keys, FL
9.9 104 reviews

Oceanside, Fee-less Pet, With Kayaks - 60 Ft Dock

apartment, Marathon
This oceanfront Marathon, Florida home is located within walking distance of Captain Hook's Marina Dive Center and Florida Keys Aquarium Encounters, offering easy access to area attractions.
This 1,030-square-foot vacation rental boasts two bedrooms, two bathrooms, a fully equipped kitchen, outdoor barbecue, patio, and included kayaks and paddleboards, perfect for exploring the Florida Keys.
Private Pool Home. Boaters Paradiselittle Torch Key. Great Fishing  Lobstering - Florida Keys, FL
9.8 34 reviews

Private Pool Home. Boaters Paradiselittle Torch Key. Great Fishing Lobstering

apartment, Big Pine Key
This apartment is located on Little Torch Key, a small island just off the Overseas Highway (US Route 1) at mile marker 28, offering a peaceful and secluded getaway. The property is approximately 30 minutes from Key West and 20 minutes from Marathon. Guests have consistently rated this rental as excellent.
This 3-bedroom, 3-bathroom apartment is perfect for families or groups of up to 8 people. The apartment has a private pool, a hot tub, a wet bar, a barbecue area, and a large dock for fishing and boating.
Oceanfront Key Largo Paradise - Private Beach + Pool, Hot Tub & Marina - Florida Keys, FL
10 307 reviews

Oceanfront Key Largo Paradise - Private Beach + Pool, Hot Tub & Marina

apartment, Tavernier
This oceanfront condo is located in the quiet town of Tavernier, just 69 miles south of Miami International Airport and 98 miles from Fort Lauderdale Airport. The apartment receives excellent user ratings for its location and amenities.
The two-bedroom, two-bathroom rental is 900 square feet and comfortably sleeps four guests. The condo offers a full kitchen, a dining area, a living room with a 55-inch Smart TV, and a private balcony with breathtaking views of the Atlantic Ocean.
Ocean Front Paradise, 6th Story Balcony Ocean View - Florida Keys, FL
9.4 6 reviews

Ocean Front Paradise, 6th Story Balcony Ocean View

apartment, Islamorada, Village of Islands
This Tavernier condo, located three miles from the Florida Keys Dive Center, Old Road Gallery, and Mariners Hospital, offers direct beach access and proximity to Islamorada's attractions.
This 1180-square-foot, two-bedroom, two-bathroom unit sleeps four and features a fully equipped kitchen, swimming pool, spa, fitness center, tennis court, and free Wi-Fi.

Frequently Asked Questions about short term rentals in Florida Keys, FL

  • What attractions should you visit during a week-long stay in the Florida Keys?

    A week in the Florida Keys offers a taste of its diverse offerings. Start in Key Largo, exploring John Pennekamp Coral Reef State Park for snorkeling or diving. Head down to Islamorada, known as the "Sport Fishing Capital of the World," and maybe try a fishing charter. Key West is a must-see, with its iconic Southernmost Point Buoy, Ernest Hemingway Home and Museum, and the vibrant Duval Street. Consider a sunset celebration at Mallory Square. Don't forget to enjoy the beaches along the way, like Bahia Honda State Park, known for its beautiful bridges and calm waters.
  • What are the best short term rentals in Florida Keys, FL?

    Among the short term rentals in Florida Keys, FL, Secret Courtyard Cottage, At Mine | Lovely Suite Steps From Duval Street and Spacious - Private 1 Bed/1 Bath Apt In Everglades are the most popular ones.

  • What types of short-term rentals are available in the Florida Keys?

    If you are looking for accommodations in the Florida Keys you can book short-term rentals which can make a huge difference. The best part about these short-term rentals is that they come in different forms and sizes. Hence, you can choose from different apartments, condos and even townhouses. Also, you can decide what size you prefer for your holidays. If you are with your partner you can choose smaller studio apartments while you can choose bigger condos for a family holiday trip. This would allow you to make the best use of the space available without having to book a hotel room. You can also look for properties that come furnished with all modern bathroom and kitchen facilities and amenities.
  • What attractions should you visit when you spend a month in the Florida Keys?

    A month gives you time for a deeper exploration. Beyond the popular spots, consider visiting the smaller islands and exploring their unique character. Spend time kayaking or paddleboarding through the mangroves. Explore the backcountry on a boat tour, discovering hidden coves and wildlife. Visit the History of Diving Museum in Islamorada. Take a day trip to Dry Tortugas National Park, a remote island with a historic fort and pristine coral reefs. Enjoy the many restaurants and local shops throughout the Keys, from Key Largo to Key West.
  • What are the best short term rentals with a pool in Florida Keys, FL?

  • What are the best kid-friendly attractions in the Florida Keys?

    1. Founders Park - Located in Islamorada, Founders Park is a great place where kids can enjoy 45 acres of fun and water activities. Here adults and kids can spend time in a splash park, play tennis, basketball and explore various walking trails.
    2. Key West Aquarium - Also, when you are exploring the Florida Keys you can visit the Key West Aquarium where you can take the kids to knowing more about marine life in their natural habitat.
    3. Calusa Beach - One of the family-friendly beaches in Florida Keys you can take kids here for an adventurous family beach day experience.
  • Can visitors to the Florida Keys witness any unique natural cycles, like cherry blossom season or autumn colors?

    No, the Florida Keys' subtropical climate doesn't experience the dramatic seasonal changes seen further north. You won't find cherry blossoms or vibrant autumn foliage. The Keys offer a more consistent, warm climate year-round, with variations in water temperature and the occasional tropical storm.
  • What are the best short term rentals with a jacuzzi in Florida Keys, FL?

    The best short term rentals with a jacuzzi in Florida Keys, FL are Secret Courtyard Cottage, Marco Beach Ocean Suites and Coco Plum Beach & Tennis Club & Marina.

  • What's the best neighbourhood to stay close to the city centre?

    If you are planning to visit the Florida Keys you can plan to stay in Key West which is probably the best place where you can find plenty of options and facilities. Choosing Key West allows you to explore several hotels and rental accommodations which can make things easier for you. Also, you can explore many beaches and local attractions which would allow you to stay close to them. You can always find plenty of dining and shopping options in Key West and that can make your holidays in Florida Keys better.
  • What are the most meaningful ways to engage with locals and discover the culture in the Florida Keys?

    To connect with the local culture, visit local restaurants and bars, like the Hogfish Bar & Grill in Islamorada, and strike up conversations. Attend a local event or festival. Explore the smaller, less touristy towns and villages. Visit art galleries showcasing local artists. Consider taking a guided tour focusing on the history and culture of the Keys. Many local businesses are family-owned and operated, offering a chance to interact with residents.
  • What are the best short term rentals for families and kids in Florida Keys, FL?

    The best short term rentals for families and kids in Florida Keys, FL are Secret Courtyard Cottage, Upper Bayview North: Waterfront 4 Bedroom Condo At Bayfront Suites & Marina and Marco Beach Ocean Suites.

  • What are the best shopping malls in the Florida Keys?

    1. Duval Square Mall - Located in Key West, Duval Square Mall is one of the best shopping places in the Florida Keys. Here you can enjoy shopping for hours and find dining options as well.
    2. Key Largo Shopping Center - If you are staying close to mainland Florida you would want to visit Key Largo Shopping Center where you can shop for hours and enjoy friendly services and delicious food.
    3. The Shops at Mallory Square - Mallory Square is one of the premier shopping destinations in Key West and this place can provide you with plenty of shops and boutiques for shopping.
  • Are there any distinctive cultural activities or hands-on workshops in the Florida Keys?

    Yes, several opportunities exist. Many art galleries offer workshops, particularly in Key West. Some resorts and local businesses offer conch shell crafting workshops. You can find opportunities for learning about local fishing techniques or even taking a class on becoming a certified diver. Check local listings for specific offerings during your visit.
  • What is the best place to book a short-term rental for the Key West Lobsterfest in the Florida Keys?

    If you are planning to attend Key West Lobsterfest in the Florida Keys you should book your short-term rental in Key West. This is one of the best towns where you can find plenty of rental accommodations. Hence, you need to evaluate and choose the best apartments and condos you can find here for your stay. These properties are fully furnished with all modern kitchen and bathroom facilities and amenities and therefore you can find the best deals here. Also, the festival happens in Key West and therefore you can stay close to the venue and explore other city attractions when you are done attending the event.
  • What are some secret spots or hidden treasures to visit in the Florida Keys?

    Some lesser-known gems include the mangrove tunnels accessible by kayak or paddleboard in various locations. Explore the quieter beaches away from the main tourist areas. Look for local fishing spots recommended by residents. Discover hidden bars and restaurants off the main streets. The best way to find these is by talking to locals and exploring beyond the well-trodden paths.
  • What should not be left out of your suitcase if you are going to the Florida Keys?

    Pack light clothing, swimwear, sunscreen (high SPF!), sunglasses, a hat, and comfortable walking shoes. Don't forget insect repellent, especially if exploring mangrove areas. A reusable water bottle is essential due to the warm climate. If you plan on water activities, pack appropriate gear like snorkeling equipment or water shoes.
  • What are the most popular festivals in the Florida Keys?

    The Florida Keys boast several festivals throughout the year. Key West's Fantasy Fest is a renowned, large-scale costumed celebration held in October. The Conch Republic Independence Celebration in Key West is a quirky and fun event. Numerous smaller festivals and events, like art walks and music festivals, take place throughout the Keys; checking local event calendars closer to your travel dates is recommended.
  • Where should you try the best local food in the Florida Keys?

    The Florida Keys offer diverse culinary experiences. For fresh seafood, many restaurants along the waterfront provide excellent options. Try a local conch fritter or a Key lime pie. Explore smaller, family-run restaurants for authentic Key West cuisine. Look for restaurants featuring locally sourced ingredients. Each island has its own unique culinary scene, so exploring different locations provides a broader taste of the Keys' food.

Nearby regions

Best Florida Keys, FL lodging with a kitchen

Tiki Time! Private Pool~tiki Hut~kayak~grill! - Florida Keys, FL
9.8 152 reviews

Tiki Time! Private Pool~tiki Hut~kayak~grill!

apartment, Marathon
This Marathon vacation rental is located just 1.2 miles from Crane Point Museum and Nature Center and within 3 miles of Florida Keys Country Club, Captain Hooks Marina and Dive Center, Sunset Park Beach, and Fishermen's Community Hospital. The home has excellent user, location, and cleanliness ratings.
This 3-bedroom, 2-bathroom house comfortably sleeps 8 guests. You'll enjoy a private pool, a fenced yard, a fully equipped kitchen, barbecue grills, and direct access to the Florida Keys.
Ocean Isles Birds Inn Paradise Vaca-25-43 - Florida Keys, FL
10 3 reviews

Ocean Isles Birds Inn Paradise Vaca-25-43

apartment, Marathon
This oceanfront apartment rental in Marathon, Florida boasts direct Atlantic Ocean access and proximity to local fishing docks.
The one-bedroom, one-bathroom condo sleeps four guests and features a kitchen with a fridge and microwave, air conditioning, a swimming pool, a garden, parking, and an open-concept design with stunning ocean views; nearby amenities include a clubhouse with an ice machine and grilling stations.
Cabana Club Suite: Key Colony Beach, Florida Keys - Florida Keys, FL
9.7 27 reviews

Cabana Club Suite: Key Colony Beach, Florida Keys

apartment, Key Colony Beach
This one-room Key Colony Beach suite is located just a short walk from the Cabana Club Pool and Beach.
The apartment has one bathroom, sleeps two guests, and features a sofa bed, private patio, and direct access to the Cabana Club Pool and Beach.
Ocean Isle Pool Ocean Front Elevator Single Level - Florida Keys, FL
10 17 reviews

Ocean Isle Pool Ocean Front Elevator Single Level

apartment, Marathon
This oceanview condo is located in a gated fishing village on Marathon Key, Florida, approximately 65 minutes from Key West International Airport (EYW).
The one-bedroom, one-bathroom unit sleeps four, features a full kitchen with stainless steel appliances and an air fryer, in-unit laundry, and access to a community pool, grilling areas, and a kayak/canoe launch.

Best Florida Keys, FL lodging with laundry available

Beautiful*water View*pool*gym Room*private Dock - Florida Keys, FL
10 10 reviews

Beautiful*water View*pool*gym Room*private Dock

apartment, Marathon
This Marathon waterfront vacation home boasts stunning views and direct access to the water, situated within three miles of the Marathon Air Museum, Captain Hooks Marina and Dive Center, and Crane Point Museum and Nature Center.
This four-bedroom, three-bathroom house sleeps ten guests and features a private balcony, swimming pool, Jacuzzi, tennis court, and fully equipped kitchen with dishwasher, offering convenient access to on-site amenities including a hot tub, barbecue grills, and laundry facilities.
Miami 3/2 Lakeside, Designed For Max  Comfort - Florida Keys, FL
10 154 reviews

Miami 3/2 Lakeside, Designed For Max Comfort

apartment, The Crossings
This lakefront apartment in The Crossings neighborhood offers a serene setting with abundant wildlife and easy access to Miami Dade College, Tamiami Airport, and Baptist Hospital. Guests rave about its excellent user, location, and cleanliness ratings.
The spacious 1350 square foot apartment has three bedrooms, two bathrooms, and a guest capacity of 10. It features a fully stocked kitchen, super fast internet, air conditioning, and a terrace/balcony. Guests can also enjoy access to a garden, spa, fitness center, and parking.
Cozy Green Apartment - Florida Keys, FL
9.2 28 reviews

Cozy Green Apartment

apartment, Homestead
This Homestead apartment rental is conveniently located within five miles of Fruit & Spice Park and Everglades Alligator Farm, and under ten miles from Homestead Miami Speedway.
The 320-square-foot unit features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, free Wi-Fi, in-unit laundry, and free on-site parking.
Quaint Spanish Colonial  House - Florida Keys, FL
9.9 402 reviews

Quaint Spanish Colonial House

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.
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