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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

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More - Florida Keys, FL
10 16 reviews

Private Cottage On Bayfront Estate With Heated Pool, Deep Dockage, Kayaks And More

cottage, Islamorada, Village of Islands
This Islamorada cottage is located in the Matecumbe district, a 3-minute walk from Islamorada Brewery & Distillery and an 11-minute walk to the History of Diving Museum.
This family-friendly vacation rental offers air conditioning, a full kitchen with a microwave and refrigerator, Wi-Fi, a swimming pool, a hot tub, and on-site parking, with kayaks and bicycles available for guest use.
Bayfront Cottage Located On The Bay In Sunset Cove With Sandy Beach - Florida Keys, FL
9.8 26 reviews

Bayfront Cottage Located On The Bay In Sunset Cove With Sandy Beach

cottage, Key Largo
This Key Largo bungalow offers direct sandy beach access and sunset views on an acre of tropical waterfront, located near Jimmy Johnson's Big Chill and Bluefin Rock Harbor Marina.
This family-friendly vacation home accommodates up to 6 guests with 2 bedrooms and 2 bathrooms, featuring a private 100ft dock with fishing equipment, complimentary kayaks, and proximity to John Pennekamp Coral Reef State Park.
Island Oasis ~ Your Paradise Awaits In Venture Out Resort! - Florida Keys, FL
9.8 18 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.
Pet Friendly Half-duplex Cottage With Kayaks And 40' Slip Option At Marina - Florida Keys, FL
9.6 8 reviews

Pet Friendly Half-duplex Cottage With Kayaks And 40' Slip Option At Marina

cottage, Marathon
This pet-friendly half-duplex in Marathon, Florida, is conveniently located near The Boat House Marina, 1.9 miles from the Florida Keys Aquarium Encounters, and within 3 miles of several dive centers.
This 500-square-foot one-bedroom, one-bathroom apartment offers a fully equipped kitchen, free Wi-Fi, private parking, and access to a terrace, garden, and concierge services, comfortably accommodating couples or small families.

Best Florida Keys, FL cottages with a garden

Private Oceanfront Cottage With Dockage, Pool Just Minutes To Key West! - Florida Keys, FL
8.8 183 reviews

Private Oceanfront Cottage With Dockage, Pool Just Minutes To Key West!

cottage, Cudjoe Key
This Cudjoe Key oceanfront cottage, located within three miles of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offers stunning ocean views and easy beach access.
This 510-square-foot vacation home features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, private patio, in-unit laundry, and access to a shared swimming pool and barbecue grills.
Cottage With Swimming Pool And Dockage, Just Minutes To Key West! - Florida Keys, FL
9.0 174 reviews

Cottage With Swimming Pool And Dockage, Just Minutes To Key West!

cottage, Cudjoe Key
This Cudjoe Key oceanfront cottage, located within three miles of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offers stunning ocean views and easy beach access.
This 390-square-foot, one-bedroom, one-bathroom vacation home sleeps two guests and features a fully equipped kitchen, laundry facilities, a patio, a swimming pool, and on-site barbecue grills.
Direct Oceanfront Cottage-sunrise View- #2, - Florida Keys, FL
8.6 208 reviews

Direct Oceanfront Cottage-sunrise View- #2,

cottage, Big Pine Key
This beachfront Summerland Key cottage, located 2.4 miles from the Big Pine Key Flea Market and 2.6 miles from the National Key Deer Refuge Visitor Center, offers stunning ocean views.
This 860-square-foot vacation home features two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, in-unit laundry, a patio, and BBQ grills; nearby activities include the Coupon Bight Aquatic Preserve and Crab Key.
Waterfront Cottage Walk To World Famous Lorelei - Florida Keys, FL
10 209 reviews

Waterfront Cottage Walk To World Famous Lorelei

cottage, Islamorada, Village of Islands
This waterfront cottage in the heart of Islamorada, Village of Islands, offers a unique and charming stay. It is within walking distance of the renowned Lorelei restaurant and numerous other attractions. With excellent user, location, and cleanliness ratings, this cottage is a top choice for travelers.
The cottage has one bedroom, one bathroom, and a spacious 1100 square feet of living space. It features a fully equipped kitchen, comfortable living areas, a private deck, and a private dock for launching paddleboards and kayaks. The cottage also has a garden, a spa, and parking.

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

Brand New 5bed/6bath Pool W/45 Foot Dockage - Available With 2 More Homes - Florida Keys, FL
10 6 reviews

Brand New 5bed/6bath Pool W/45 Foot Dockage - Available With 2 More Homes

cottage, Marathon
This five-bedroom, six-bathroom Marathon vacation home is conveniently located within three miles of Crane Point Museum, the Marathon Air Museum, Florida Keys Country Club, Captain Hooks Marina, and the Marathon Visitor Center.
This smoke-free rental boasts a private balcony, in-unit laundry, a fully equipped kitchen including a dishwasher, a swimming pool, hot tub, and barbecue grills, comfortably accommodating up to twelve guests.
Mile Marker Mahi - Venture Out #465 - Florida Keys, FL
9.6 55 reviews

Mile Marker Mahi - Venture Out #465

cottage, Cudjoe Key
This Cudjoe Key cottage is a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to the island's attractions. With an excellent user rating, it's a popular choice for travelers seeking a relaxing and comfortable stay.
The two-bedroom, two-bathroom home comfortably accommodates four guests and features a fully equipped kitchen, a private patio, and a spa tub. Guests can enjoy the beautiful ocean views, relax in the spa tub, and grill fresh seafood on the barbecue.
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.
Carpe' Diem Heart Of The Fl. Keys Specials - Florida Keys, FL
8.8 157 reviews

Carpe' Diem Heart Of The Fl. Keys Specials

cottage, Marathon
Carpe'Diem is a three-bedroom, two-bathroom apartment ideally located in Marathon, Florida Keys, at Mile Marker 50.3, offering direct access to the Great Atlantic for boating, fishing, and diving. This very good-rated apartment is only a few steps from the deck and dock, making it convenient for children and seniors.
The apartment features a fully equipped kitchen, three bedrooms, two full baths, a screened-in lanai, a 50-foot furnished dock with a six-person spa tub and gas grill, air conditioning, internet, parking, and a garden.

Best pet friendly Florida Keys, FL cottages

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

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.
Fl Keys Cottage With Ocean Views - Venture Out Unit 395 - Florida Keys, FL
8.4 8 reviews

Fl Keys Cottage With Ocean Views - Venture Out Unit 395

cottage, Cudjoe Key
This Cudjoe Key cottage is located a short walk from Venture Key, Venture Out Keys, and Out Key, offering easy access to the natural beauty of the area. It is also just a few miles from Florida Keys Beaches, providing a peaceful and tranquil setting for your stay. This highly-rated cottage is perfect for a small family or group of friends seeking a relaxing getaway.
The cottage offers 650 square feet of space, with two bedrooms, one bathroom, and a capacity for six guests. Enjoy amenities like a swimming pool, jacuzzi, and a fully equipped kitchen, as well as outdoor grilling and a prime seafront location.
Starfish Cottage - Sleeps Up To 4 People - Florida Keys, FL
9.8 64 reviews

Starfish Cottage - Sleeps Up To 4 People

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.
Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach - Florida Keys, FL
8.0 2 reviews

Ocean Front Unit In Islamorada | Enjoy Scenic Walks On Private Beach

cottage, Islamorada, Village of Islands
This Islamorada beachfront cottage in Matecumbe offers direct ocean access, a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Center, and under a mile from the Hurricane Monument and Florida Keys Brewing Co.
The 450-square-foot, one-bedroom, one-bathroom vacation home sleeps four and includes a private balcony, air conditioning, Wi-Fi, a swimming pool, parking, and concierge services.
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