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Florida Keys, FL cottages
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277 Best cottages in Florida Keys, FL

Best family friendly Florida Keys, FL cottages

Among the 277 accommodations in Florida Keys, FL, here are the 4 best family friendly cottages

35' Seawall Sparkling , 30min From Keywest, Wifi, Bbq Grill, Pool - Florida Keys, FL
9.8 132 reviews

35' Seawall Sparkling , 30min From Keywest, Wifi, Bbq Grill, Pool

cottage, Cudjoe Key
This 2-bedroom, 2-bathroom mobile home is located in Summerland Key, just a short distance from the beach and a short walk to the amenities of Venture Out Residential Condominium. The property has received excellent user ratings and offers a comfortable and convenient stay for travelers visiting Cudjoe Key.
The 850-square-foot mobile home can comfortably accommodate up to 6 guests. It features a well-equipped kitchen, a spacious living area with a pull-out queen sleeper sofa, a large Smart TV, and a private patio with stunning waterfront views. Guests can enjoy access to a community pool, hot tub, marina, store, recreation hall, and tennis courts, all within walking distance.
Cottage With Dock Space - Florida Keys, FL
10 1 review

Cottage With Dock Space

cottage, Islamorada, Village of Islands
This Islamorada canal-front home, minutes from the Snake Creek Bridge and close to Theater of the Sea, Founders Park, restaurants, and shops, offers direct canal access with manatee sightings.
The two-bedroom, one-bathroom house sleeps four, features a private dock, BBQ grill, swimming pool, and all the comforts of home including internet access, a full kitchen, and air conditioning.
Palm Cottage - Sleeps 4  Summer Fun ..Lobster Season. - Florida Keys, FL
9.8 55 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.
Wonderful Chalet, With Terrace & Private Patio  20 Miles From Key West. - Florida Keys, FL
10 45 reviews

Wonderful Chalet, With Terrace & Private Patio 20 Miles From Key West.

cottage, Cudjoe Key
This smoke-free cottage is located in Summerland Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, and less than four miles from Florida Keys Beaches. This "Little Gem In Paradise" is rated excellent by guests and offers a peaceful garden setting perfect for relaxing.
This one-bedroom, one-bathroom cottage can accommodate up to four guests and features a private garden, terrace, and patio. Enjoy amenities like a fully equipped kitchen, washer/dryer, free WiFi, a swimming pool, a tennis court, and barbecue grills.

Best Florida Keys, FL cottages with a garden

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Florida Keys, FL
9.0 64 reviews

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

cottage, Cudjoe Key
This waterfront cottage is located in Cudjoe Key, just a short distance from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering a peaceful and laid-back atmosphere. Guests consistently rate this property as excellent. This two-bedroom, one-bathroom cottage offers 750 square feet of space, comfortably accommodating up to four guests. Amenities include a fully equipped kitchen, a private garden, a swimming pool, and a barbecue grill, perfect for enjoying the Florida Keys lifestyle.
46 M² Cottage ∙ 1 Bedroom ∙ 3 Guests - Florida Keys, FL
No reviews

46 M² Cottage ∙ 1 Bedroom ∙ 3 Guests

cottage, Marathon
This oceanside cottage in Marathon Key, Florida, offers a prime location with a large yard for boat and RV parking, situated 2.2 miles from Sombrero Beach and 2.7 miles from boat ramps.
This 500 square foot rental accommodates up to 3 guests in one bedroom and a pull-out sofa, featuring a full kitchen, air conditioning, a terrace, garden, on-site laundry, and complimentary kayaks, with an optional boat dock available 2.4 miles away at The Boat House Marina.
Flamingo Cottage Summer Fun. Pool, Boating, Fishing Lobster Season. - Florida Keys, FL
9.8 47 reviews

Flamingo Cottage Summer Fun. Pool, Boating, Fishing Lobster Season.

cottage, Cudjoe Key
The Flamingo Cottage is located in Summerland Key, just a short walk from Tonio's tiki bar and a 25-mile drive from Key West. This charming cottage boasts excellent ratings, making it a popular choice for travelers seeking a relaxing getaway. The cottage offers a private space with a full kitchen, accommodating up to four guests. Amenities include a shared outdoor pool, covered patio with a gas grill, and picnic area, providing opportunities for both relaxation and social gatherings.
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Florida Keys, FL
8.6 84 reviews

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

cottage, Cudjoe Key
This waterfront cottage is located on Cudjoe Key, just a short drive from Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offering easy access to popular attractions and activities. It has received very good user ratings, making it a popular choice for travelers.
The cottage has two bedrooms and one bathroom, providing comfortable accommodations for up to four guests. It features a fully equipped kitchen, a private pool, a terrace, a garden, and laundry facilities for a convenient and enjoyable stay.

Frequently Asked Questions about cottages in Florida Keys, FL

  • What are the top must-see attractions in the Florida Keys?

    The Florida Keys offer a plethora of attractions. For natural beauty, you can't miss Dry Tortugas National Park, with its historic fort and pristine coral reefs. Then there's Bahia Honda State Park, known for its gorgeous beach and old railroad bridge. For a taste of Key West, explore Duval Street, Mallory Square for the sunset celebration, and Ernest Hemingway's Home and Museum. Further up the Keys, John Pennekamp Coral Reef State Park provides incredible snorkeling and diving opportunities.
  • What are the best cottages in Florida Keys, FL?

  • How to spend a 5-day holiday in the Florida Keys?

    A five-day trip allows for a good exploration. Spend a day or two in Key West, enjoying the nightlife, history, and beaches. Allocate another day for exploring Dry Tortugas National Park, perhaps taking a boat tour. Consider a day trip to Islamorada, known as the Sport Fishing Capital of the World, for some water activities. Finally, spend a day relaxing on one of the many beautiful beaches in the Keys, like Bahia Honda State Park or Sombrero Beach.
  • What are the best cottages with a pool in Florida Keys, FL?

  • Are the Florida Keys a good destination to rent a cottage?

    Absolutely! The Florida Keys have many charming cottages available for rent, particularly in quieter areas like Islamorada or Marathon. These offer a more secluded and homey experience compared to hotels, perfect for a relaxing getaway. Look for rentals on websites specializing in vacation homes.
  • What are the best cottages with a jacuzzi in Florida Keys, FL?

  • What weather, wildlife, or natural hazards might affect travelers in the Florida Keys?

    The Keys have a subtropical climate, meaning hot and humid summers and mild winters. Hurricane season runs from June 1st to November 30th, so check forecasts before and during your trip. Wildlife includes various birds, sea turtles, and manatees. Be mindful of strong currents and potential encounters with marine life while swimming or snorkeling. Mosquitoes can be prevalent, especially in the evenings.
  • What are the best cottages for families and kids in Florida Keys, FL?

    The best cottages for families and kids in Florida Keys, FL are Secret Courtyard Cottage, 3br/3ba Sunset Cottage Located At The Villages Of Hawks Cay and Redlands Bungalow.

  • Are the Florida Keys pedestrian and cyclist-friendly?

    Key West, in particular, is quite pedestrian-friendly, especially in the downtown area. However, cycling is more challenging due to the traffic on some roads. Many areas have dedicated bike paths, and renting bikes is popular. In other parts of the Keys, car travel is often necessary due to distances between attractions.
  • What are the best pet friendly cottages in Florida Keys, FL?

  • Are there any unusual or hidden places to explore in the Florida Keys?

    Yes! The African Queen, a historic steamboat, is docked in Key Largo and offers tours. Furthermore, explore the backcountry roads for hidden beaches and nature trails. Consider visiting the less-visited state parks like Curry Hammock State Park for a more secluded experience.
  • What are the best cottages with parking in Florida Keys, FL?

  • What are some of the best cultural experiences that allow you to meet locals in the Florida Keys?

    Attending local events and festivals is a great way to interact with locals. Check local listings for smaller community events. Many restaurants and bars offer live music, creating opportunities for casual conversations. Visiting local art galleries and shops can also lead to interactions with artists and owners.
  • What are the best authentic dishes to taste in the Florida Keys?

    Fresh seafood is a must! Key lime pie is iconic, and you'll find many variations. Conch fritters are a popular appetizer, and stone crab claws are a seasonal delicacy. Many restaurants offer locally sourced ingredients, highlighting the Keys' culinary scene.
  • Are there any recommended items to pack for a stay in the Florida Keys?

    Pack light, breathable clothing for the warm weather. Sunscreen, sunglasses, and a hat are essential for sun protection. Bring swimwear, a reusable water bottle, and comfortable walking shoes. Insect repellent is also recommended, particularly for evening activities. If you plan on water activities, bring appropriate gear.

Nearby regions

Best Florida Keys, FL cottages with jacuzzi

Among the 277 accommodations in Florida Keys, FL, here are the 4 best cottages with a jacuzzi

Breezy Point - Venture Out Unit 199 - Florida Keys, FL
No reviews

Breezy Point - Venture Out Unit 199

cottage, Cudjoe Key
This Summerland Key cottage, a short drive from Cudjoe Key, boasts an oceanfront location near the beaches of the Keys archipelago and Upper Sugarloaf Key.
The 750-square-foot vacation home features two bedrooms, one bathroom, and accommodates up to six guests, offering a private patio with a barbecue, a shared pool and hot tub, and in-unit laundry.
Island Oasis ~ Your Paradise Awaits In Venture Out Resort! - Florida Keys, FL
9.6 14 reviews

Island Oasis ~ Your Paradise Awaits In Venture Out Resort!

cottage, Cudjoe Key
Island Oasis ~ Your Paradise Awaits in Venture Out Resort! is a waterfront cottage in Cudjoe Key, Florida, a short walk from Venture Out Keys, Venture Key, and Out Key, and 2.4 miles from Florida Keys Beaches.
This two-bedroom, two-bathroom vacation home sleeps six and features a fully equipped kitchen, private balcony, swimming pool, tennis court, and access to barbecue grills.
Tidewater Views At Venture Out - Florida Keys, FL
9.8 264 reviews

Tidewater Views At Venture Out

apartment, Cudjoe Key
This Cudjoe Key cottage is a short 15-minute walk from Venture Key and Venture Out Keys, offering a peaceful escape near the beautiful Florida Keys. The cottage has received excellent ratings for location, cleanliness, and overall user experience.
The 850-square-foot cottage comfortably accommodates up to 6 guests in its two bedrooms and two bathrooms. Enjoy the convenience of a fully equipped kitchen, a private patio, a spa tub, a swimming pool, and a barbecue grill for relaxing evenings.
Beautiful Cottage & Amenities In Gated Community - Florida Keys, FL
10 2 reviews

Beautiful Cottage & Amenities In Gated Community

cottage, Cudjoe Key
This Cudjoe Key vacation home is conveniently located in Summerland Key, a short 10-minute walk from Venture Out Keys, Venture Key, and Out Key, and a 2.4-mile drive to Florida Keys Beaches.
The two-bedroom, two-bathroom cottage sleeps five, features a fully equipped kitchen, private pool, jacuzzi, tennis court, BBQ grills, game room, and free Wi-Fi.

Best pet friendly Florida Keys, FL cottages

Among the 277 accommodations in Florida Keys, FL, here are the 4 best pet friendly cottages

Waterfront Key Colony Beach Home W/ Golf Cart! - Florida Keys, FL
No reviews

Waterfront Key Colony Beach Home W/ Golf Cart!

cottage, Key Colony Beach
This Key Colony Beach vacation home is conveniently located within two miles of Sunset Park Beach, Marathon Visitor Center, Curry Hammock State Park, San Pablo Catholic Church, and Captain Hooks Marina and Dive Center.
This pet-friendly rental boasts two bathrooms, a fully equipped kitchen, a private patio, and access to an outdoor pool and barbecue grills; free WiFi is available in public areas.
Beachy Getaway With Pool, Water Views, Furnished Patio, & Dock Access - Florida Keys, FL
9.0 36 reviews

Beachy Getaway With Pool, Water Views, Furnished Patio, & Dock Access

cottage, Key Colony Beach
This canalfront vacation home in Key Colony Beach is centrally located, a half-mile from the Cabana Club amenities and beach, and within walking distance of Key Colony Beach Golf.
This 840 sq ft rental accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen, air conditioning, a private boat dock, and convenient access to local attractions like the Dolphin Research Center and Sunset Park.
Starfish Cottage - Summer Fun.  Sleeps 4 -Boating Fishing And Lobster  Season. - Florida Keys, FL
9.8 62 reviews

Starfish Cottage - Summer Fun. Sleeps 4 -Boating Fishing And Lobster Season.

cottage, Cudjoe Key
The New Hidden Hammock Resort - Pink Cottage Unit #3, a seaside cottage in Cudjoe Key, Florida, is less than one mile from Florida Keys Beaches and Crab Key, and within six miles of the Big Pine Key Flea Market and the National Key Deer Refuge Visitor Center.
This 550-square-foot, one-bedroom, one-bathroom unit sleeps four and features a fully equipped kitchen, private balcony, free WiFi, a swimming pool, and access to outdoor gas grills.
Sea Breeze Cottage - Venture Out Unit 066 - Florida Keys, FL
8.0 17 reviews

Sea Breeze Cottage - Venture Out Unit 066

cottage, Cudjoe Key
Sea Breeze Cottage is located in Summerland Key, within walking distance to the ocean and close to Florida Keys Beaches, Coupon Bight Aquatic Preserve, Blue Hole, and Big Munson Island.
This 800 sq ft cottage accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, offering amenities such as air conditioning, a swimming pool, jacuzzi, Wi-Fi, and is pet-friendly for up to two pets under 25 lbs.
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