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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

Flakey's - Florida Keys, FL
9.9 215 reviews

Flakey's

apartment, Islamorada, Village of Islands
This Islamorada rental is located on Morada Way in the Art and Culture district, just a short walk from the World Wide Sportsman Marina and directly across the street from Morada Bay. The accommodation has excellent user, location, and cleanliness ratings.
The two-bedroom, one-bathroom rental can accommodate up to six guests. The rental features a fully equipped kitchen, two balconies, fast WiFi, Xfinity cable, and a backyard garden that hosts live music and art classes.
Key Largo Sunsets Penthouse On The Ocean - Florida Keys, FL
9.8 197 reviews

Key Largo Sunsets Penthouse On The Ocean

apartment, Key Largo
This Key Largo apartment is conveniently located near popular attractions like Baker's Cay Resort Beach, Jimmy Johnson's Big Chill, and Jacob's Aquatic Center, all within a 2-mile radius. This unit has received excellent ratings for its cleanliness, location, and overall user experience.
The apartment features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a tennis court, and free Wi-Fi.
Cozy Family Home- 5 Minutes From Sombrero Beach - Florida Keys, FL
10 99 reviews

Cozy Family Home- 5 Minutes From Sombrero Beach

apartment, Marathon
This cozy family home is located in Marathon, just a 5-minute drive from Sombrero Beach, and within a short distance of both Florida Keys Aquarium Encounters and Captain Hook's Marina Dive Center. It has earned excellent ratings for location, cleanliness, and user experience, making it a great choice for travelers looking for a comfortable and convenient stay.
The 1150 square foot home comfortably accommodates up to 6 guests, offering a relaxing and enjoyable vacation experience. This Marathon home features a private pool, a hot tub, a garden with a barbecue, and a fully equipped kitchen, allowing you to enjoy your vacation to the fullest.
Deja Blue Suite  [Ocean Pointe 1409] - Florida Keys, FL
9.8 172 reviews

Deja Blue Suite [Ocean Pointe 1409]

apartment, Tavernier
This waterfront apartment is located in Tavernier, Florida, just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys waters. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
This 2-bedroom, 2-bathroom apartment comfortably accommodates up to 6 guests in its 980 square feet of space. The apartment offers a range of amenities for a relaxing stay, including a swimming pool, a spa, a tennis court, and a garden, as well as a fully equipped kitchen and free WiFi.

Best Florida Keys, FL lodging with a balcony

Luxury 4br Villa Private Jacuzzi & Billiard - Florida Keys, FL
No reviews

Luxury 4br Villa Private Jacuzzi & Billiard

apartment, Princeton
This 1-bedroom residence is located in Homestead, offering easy access to Fruit Spice Park, Homestead Air Force Base, Homestead Miami Speedway, and Florida Keys Factory Shops, all within a 7-mile radius.
This spacious 12,920 sq ft apartment includes a private jacuzzi, a fully equipped kitchen with a dishwasher and oven, free WiFi, and on-site parking, accommodating up to 19 guests.
Oceanfront 5th Floor Penthouse - Florida Keys, FL
9.8 149 reviews

Oceanfront 5th Floor Penthouse

apartment, Key Largo
This Key Largo apartment is located near the ocean, within walking distance of Baker's Cay Resort Beach and Jimmy Johnson's Big Chill, and within a short drive of Jacob's Aquatic Center and Bluefin Rock Harbor Marina. The property has been rated excellent for its location and user experience, and very good for cleanliness.
This 2-bedroom, 2-bathroom unit offers 1350 square feet of space and can comfortably accommodate up to 6 guests. Enjoy amenities like a private fenced yard, a swimming pool, a tennis court, and a fully equipped kitchen, perfect for a relaxing and enjoyable vacation.
P38 - Charming 1 Bedroom, Waterfront Duplex With P - Florida Keys, FL
9.7 53 reviews

P38 - Charming 1 Bedroom, Waterfront Duplex With P

apartment, Key Colony Beach
This waterfront vacation home is located in Key Colony Beach, just a short walk from Sunset Park Beach and Coco Plum Beach, offering easy access to the area's beautiful beaches and nearby attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom rental can comfortably accommodate up to three guests and features a private pool, a spa tub, and a barbecue grill for outdoor enjoyment. The house also includes modern amenities like free WiFi, a fully equipped kitchen, and a washing machine for added convenience.
Tiki Time! Private Pool~tiki Hut~kayaks~grill! - Florida Keys, FL
9.8 147 reviews

Tiki Time! Private Pool~tiki Hut~kayaks~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.

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

Villa Valbuena Azul Escape 2 Kings Key Largo Pickleball Tennis Pool Lagoon - Florida Keys, FL
9.8 271 reviews

Villa Valbuena Azul Escape 2 Kings Key Largo Pickleball Tennis Pool Lagoon

apartment, Key Largo
This Key Largo apartment is conveniently located just a short drive from John Pennekamp State Park, Pigeon Key, and Windley Key, offering easy access to the area's top attractions. It boasts excellent ratings for location, cleanliness, and overall user experience.
The apartment features two bedrooms, making it ideal for families or groups of friends. Guests can enjoy a private beach, free bikes and kayaks, tennis and pickleball courts, a swimming pool, and a fully equipped kitchen.
Spring & Summer Dates Available Licensed Rental Vr #25-0235  No Boats - Florida Keys, FL
10 61 reviews

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

apartment, Islamorada, Village of Islands
This family-friendly condo building is directly on the beach in Islamorada, just a short distance from Islamorada County Park and Founders Park. Guests consistently rate this accommodation as excellent.
This 2-bedroom, 2-bathroom condo offers 800 square feet of space and can comfortably accommodate up to 6 guests. Enjoy amenities like a swimming pool, fitness center, tennis court, and a fully equipped kitchen, perfect for a relaxing and enjoyable stay.
July/aug. Save$ Waterfront 4 Bike/2 Kayak King Bed - Florida Keys, FL
9.5 446 reviews

July/aug. Save$ Waterfront 4 Bike/2 Kayak King Bed

apartment, Cudjoe Key
This vacation home is located in Summerland Key, just a short walk from Venture Key and Venture Out Keys, offering easy access to local attractions and activities. It has received excellent ratings for location, cleanliness, and overall user experience.
The 2-bedroom, 2-bathroom home spans 860 square feet and can comfortably accommodate up to 6 guests. Enjoy a range of amenities including a private pool, spa, tennis court, and a fully equipped kitchen, perfect for creating memorable vacation experiences.
Garden Cottage Near Miami, Everglades & Florida Keys - Florida Keys, FL
9.5 128 reviews

Garden Cottage Near Miami, Everglades & Florida Keys

apartment, Princeton
Maria's Los Cirhuelos is a 500-square-foot apartment located in Homestead, Florida, approximately 3.4 miles from Fruit Spice Park and 6.7 miles from Florida Keys Factory Shops.
This Princeton apartment offers a private garden, outdoor seating, free Wi-Fi, a fully equipped kitchen, air conditioning, a private entrance, and free private parking.

Best Florida Keys, FL lodging with laundry available

Key Largo Coastal Condo-ocean View ~ Pool ~ Beach - Florida Keys, FL
9.8 211 reviews

Key Largo Coastal Condo-ocean View ~ Pool ~ Beach

apartment, Tavernier
This waterfront condo is located in Tavernier, a short 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, and within 3 miles of Mariners Hospital and Florida Keys Dive Center. This rental has excellent user, location, and cleanliness ratings.
The condo has one bedroom, one bathroom, and can accommodate up to three guests in its 580 square feet. Enjoy the pool, spa, tennis court, and other amenities, including a fully equipped kitchen, a fireplace, and a washer and dryer.
Island Palms~overlooking Tennis Courts - Florida Keys, FL
9.8 156 reviews

Island Palms~overlooking Tennis Courts

apartment, Key Largo
This Key Largo yacht is located in Kawama Yacht Club, a gated community at mile marker 100, situated within John Pennekamp Coral Reef State Park and half a mile from Pilot House Marina. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The yacht spans 1190 square feet and comfortably accommodates up to six guests in its two bedrooms and two bathrooms. Enjoy swimming, snorkeling, kayaking, and paddle boarding in the 3-acre saltwater lagoon, explore John Pennekamp Coral Reef State Park, and take advantage of the on-site tennis/pickleball courts, children's playground, and jetty.
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Florida Keys, FL
8.6 98 reviews

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West

cottage, Cudjoe Key
This charming cottage is situated in Summerland Key, just a short drive from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering a peaceful retreat in the Florida Keys. It has received excellent ratings from previous guests, making it a popular choice for travelers. This cozy cabin provides 750 square feet of space, comfortably accommodating up to four guests in its two bedrooms and one bathroom. Enjoy a refreshing dip in the private pool, grill up a meal on the barbecue, and stay connected with free Wi-Fi.
Ocean Breeze @ Vo - Kayaks, Bikes, 30 Min From Kw - Florida Keys, FL
9.6 37 reviews

Ocean Breeze @ Vo - Kayaks, Bikes, 30 Min From Kw

apartment, Cudjoe Key
This Cudjoe Key vacation home sits across from the open water, offering direct ocean views and a 30-minute drive to Duval Street in Key West.
The one-bedroom, one-bathroom cottage sleeps three, features a remodeled interior with a large enclosed porch, kayaks, bikes, a private pool and Jacuzzi, and access to resort amenities including tennis and pickleball courts for a $125 resort fee.
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