Cottages in Florida Keys at the best prices

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Florida Keys cottages
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277 Best cottages in Florida Keys

Best family friendly Florida Keys cottage rentals

Among the 277 accommodations in Florida Keys, here are the 4 best family friendly cottage rentals

Island Oasis ~ Your Paradise Awaits In Venture Out Resort! - Florida Keys
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, conveniently located within a 2.4-kilometre radius of Florida Keys Beaches and a 15-minute walk from Venture Out Keys, Venture Key, and Out Key.
This two-bedroom, two-bathroom holiday home sleeps six guests and boasts a fully equipped kitchen, private balcony, swimming pool, tennis court, and access to barbecue grills; enjoying stunning views and easy water access.
Pet Friendly Half-duplex Cottage With Kayaks And 40' Slip Option At Marina - Florida Keys
9.6 8 reviews

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

cottage, Marathon
This pet-friendly apartment in Marathon, Florida Keys, is conveniently located near The Boat House Marina, approximately 3km from the Florida Keys Aquarium Encounters, and within 5km of several dive centres.
The 46-square-metre, one-bedroom, one-bathroom property offers a fully equipped kitchen, terrace, free Wi-Fi, private parking, and access to local activities such as cycling, fishing, and canoeing.
Lush Tropical Setting With Dockage - Charming Coastal Retreat - Florida Keys
No reviews

Lush Tropical Setting With Dockage - Charming Coastal Retreat

cottage, Islamorada, Village of Islands
This waterside holiday home in Islamorada, Village of Islands, is situated directly on Florida Bay at mile marker 82.2, offering protected boat dockage and close proximity to John Pennekamp Coral Reef State Park, Theater of the Sea, and Robbie's Marina.
This family-friendly bungalow accommodates up to 6 guests and features a ground-floor layout with a king bedroom, an en-suite bathroom, and an enclosed sunroom that functions as a second bedroom, alongside essential amenities like WiFi, air conditioning, and parking.
Cottage With Pool  And Boat Dockage Just Minutes To Key West! - Florida Keys
8.6 168 reviews

Cottage With Pool And Boat Dockage Just Minutes To Key West!

cottage, Cudjoe Key
This Cudjoe Key waterfront cottage, situated within 5km of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offers stunning views and direct water access.
The 36 square metre property sleeps two in one bedroom, one bathroom, and boasts a fully equipped kitchen, private terrace, swimming pool, garden, and barbecue facilities.

Best Florida Keys cottages with a garden

Brand New 5bed/6bth Pool W/76 Ft Of Dockage- 2 Homes Next Door Available As Well - Florida Keys
10 7 reviews

Brand New 5bed/6bth Pool W/76 Ft Of Dockage- 2 Homes Next Door Available As Well

cottage, Marathon
This five-bedroom, six-bathroom holiday home in Marathon, Florida Keys, is located within 5km of Crane Point Museum, Marathon Air Museum, Florida Keys Country Club, Captain Hooks Marina, and the Marathon Visitor Centre.
Sleeping up to twelve guests, this self-catering property boasts a private swimming pool, jacuzzi, terrace, garden, parking, and in-unit laundry facilities, along with a fully equipped kitchen and smart TV; barbecue grills and a hot tub are also available for guest use.
Direct Oceanfront Cottage-sunrise View- #2, - Florida Keys
8.6 208 reviews

Direct Oceanfront Cottage-sunrise View- #2,

cottage, Big Pine Key
This beachfront Summerland Key holiday home offers direct ocean access, situated 3.9km from the Big Pine Key Flea Market and 4.2km from the National Key Deer Refuge Visitor Centre.
The 80-square-metre property sleeps four guests in two bedrooms and one bathroom, and includes a fully equipped kitchen, patio, garden, spa, and on-site parking, plus a washing machine.
Imagine In The Keys - Venture Out Unit 073 - Florida Keys
9.6 4 reviews

Imagine In The Keys - Venture Out Unit 073

cottage, Cudjoe Key
This Cudjoe Key waterfront holiday home, situated 3.9km from Florida Keys Beaches and 9.7km from Upper Sugarloaf Key and Upper Sugarloaf Sound, offers stunning water views and direct water access.
The 74 square metre property boasts two bedrooms, two bathrooms, a private patio, swimming pool, jacuzzi, and barbecue facilities, sleeping up to six guests.
Carpe' Diem Heart Of The Fl. Keys Specials - Florida Keys
8.8 157 reviews

Carpe' Diem Heart Of The Fl. Keys Specials

cottage, Marathon
This ground-floor house is situated in Marathon, Florida, at Mile Marker 50.3, offering direct access to the Atlantic Ocean and being minutes away from the beach, transport, shops, and restaurants. The property has received excellent user ratings, making it a popular choice for travellers.
This three-bedroom property, covering 130 square metres, comfortably accommodates up to four guests. The house features a fully equipped kitchen, a spacious living area, a dining area, a private garden, a Jacuzzi, and a 50-foot dock with a hot tub, gas grill, and a boat lift.

Frequently Asked Questions about cottages in Florida Keys

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

    The Florida Keys offer a plethora of attractions. For natural beauty, you can't beat the Dry Tortugas National Park, accessible by boat or seaplane, with its historic fort and pristine coral reefs. Then there's Bahia Honda State Park, known for its stunning beaches and old railroad bridge. For a taste of Key West, visit Mallory Square for the sunset celebration, explore Duval Street's vibrant atmosphere, and see Ernest Hemingway's Home and Museum. Further up the Keys, John Pennekamp Coral Reef State Park offers incredible snorkeling and diving opportunities.
  • What are the best cottage rentals in Florida Keys?

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

    A five-day trip allows for a good exploration. Spend a day or two in Key West, soaking up the atmosphere, visiting the Hemingway House, and enjoying the sunset at Mallory Square. Allocate another day for exploring Dry Tortugas National Park. Consider a day trip to Islamorada, known as the "Sport Fishing Capital of the World," for some fishing or exploring the Theater of the Sea. The remaining day could be spent relaxing on the beaches of Bahia Honda State Park or exploring other areas that catch your interest, like Marathon or Key Largo.
  • What are the best cottage rentals with a pool in Florida Keys?

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

    Absolutely! The Florida Keys offer a wide variety of vacation rentals, including many charming cottages. You'll find them throughout the Keys, from Key Largo to Key West, offering a more intimate and homey experience than a hotel. Many are located near beaches or other attractions, providing easy access to activities and local life.
  • What are the best cottage rentals with a jacuzzi in Florida Keys?

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

    The Keys have a subtropical climate. Expect hot, humid weather, especially during summer. Hurricane season runs from June 1st to November 30th, so it's crucial to check forecasts before and during your trip. Wildlife encounters are common; be aware of mosquitoes, especially in the mangroves. Be mindful of strong currents and potential riptides when swimming. Also, be aware of the presence of venomous marine life, like certain types of fish and jellyfish.
  • What are the best cottage rentals for families and kids in Florida Keys?

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

  • Are the Florida Keys, United States pedestrian and cyclist-friendly?

    Key West, in particular, is quite pedestrian-friendly, especially in the downtown area. However, cycling can be challenging in some areas due to traffic and a lack of dedicated bike lanes on many roads. In other parts of the Keys, car travel is more common. Always prioritize safety and be aware of traffic conditions when walking or cycling.
  • What are the best pet friendly cottage rentals in Florida Keys?

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

    Yes! The African Queen, a historic boat featured in the movie of the same name, is a unique attraction in Key Largo. Further, explore the backcountry roads and find hidden beaches, or take a boat trip to explore secluded mangrove islands and discover hidden coves. Look for local guides who can take you to less-visited spots.
  • What are the best cottage rentals with parking in Florida Keys?

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

    Attending local events and festivals is a great way to meet people. Check local listings for smaller community gatherings. Many restaurants and bars offer a relaxed atmosphere where you can interact with locals. Consider taking a guided kayaking or snorkeling tour; the guides are often locals and can share insights into the area's culture and history.
  • What are the best authentic dishes to taste in the Florida Keys, United States?

    Fresh seafood is a must! Key West pink shrimp, stone crabs (in season), and conch fritters are local favorites. Many restaurants offer variations of Key lime pie, a classic dessert. Look for restaurants that source their ingredients locally; you'll find the freshest and most authentic dishes.
  • Are there any recommended items to pack for a stay in the Florida Keys, United States?

    Pack light, breathable clothing suitable for warm, humid weather. Don't forget swimwear, sunscreen (high SPF), a hat, sunglasses, and insect repellent. If you plan on watersports, bring appropriate gear. Comfortable walking shoes are essential, especially for exploring Key West. Consider bringing a reusable water bottle to stay hydrated.

Nearby regions

Best Florida Keys cottage rentals with jacuzzi

Among the 277 accommodations in Florida Keys, here are the 4 best cottage rentals with a jacuzzi

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

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

cottage, Islamorada, Village of Islands
This holiday home is situated in the Matecumbe district of Islamorada, a 3-minute walk from Islamorada Brewery & Distillery and an 11-minute walk from the History of Diving Museum.
Guests can enjoy a communal swimming pool and hot tub, with amenities including a kayak and bicycles provided for outdoor activities, alongside on-site parking and complimentary Wi-Fi.
Breezy Point - Venture Out Unit 199 - Florida Keys
No reviews

Breezy Point - Venture Out Unit 199

cottage, Cudjoe Key
Breezy Point cottage, a two-bedroom holiday home in Summerland Key, offers easy access to Bahia Honda State Park and other Florida Keys attractions, a short drive away.
This 70 square metre property features a combined kitchen-diner, sleeps six guests comfortably, and includes amenities such as air conditioning, Wi-Fi, a BBQ grill, and an 18ft driveway.
Sea Breeze Cottage - Venture Out Unit 066 - Florida Keys
8.0 17 reviews

Sea Breeze Cottage - Venture Out Unit 066

cottage, Cudjoe Key
Sea Breeze Cottage, a holiday home in Summerland Key, is located just a short walk from the ocean and offers easy access to Florida Keys Beaches and Coupon Bight Aquatic Preserve, with attractions like Blue Hole and Big Munson Island nearby. This pet-friendly lodge spans 74 square metres, providing two bedrooms and two bathrooms to accommodate up to four guests, and features air conditioning, a swimming pool, a jacuzzi, and a kitchen equipped with a fridge and microwave oven.
Charming Bayfront Cottage In Heart Of Islamorada With Heated Pool, Deep Dockage, Kayaks & More - Florida Keys
10 19 reviews

Charming Bayfront Cottage In Heart Of Islamorada With Heated Pool, Deep Dockage, Kayaks & More

cottage, Islamorada, Village of Islands
This detached house in the Matecumbe district of Islamorada offers a beachfront location, just a 3-minute walk to Islamorada Brewery & Distillery and an 11-minute walk to the History of Diving Museum.
Guests can enjoy a family-friendly stay with amenities including air conditioning, a full kitchen, complimentary Wi-Fi, a swimming pool, jacuzzi, garden, spa, parking, and access to on-site kayaks and bicycles for exploring the Village of Islands.

Best pet friendly Florida Keys cottage rentals

Among the 277 accommodations in Florida Keys, here are the 4 best pet friendly cottage rentals

Canal Front Home With Easy Ocean Access - Florida Keys
8.6 188 reviews

Canal Front Home With Easy Ocean Access

cottage, Cudjoe Key
This waterfront cottage is located in Cudjoe Key, just a 1.6km walk from Venture Key, Venture Out Keys, and Out Key, making it a convenient base for exploring the area. The cottage has consistently received very good ratings from previous guests.
The Waterfront Home offers 76 square metres of space, accommodating up to 4 guests in its two bedrooms. The cottage has a range of amenities, including a swimming pool, Jacuzzi, tennis court, and a barbecue, making it perfect for families or groups looking for a relaxing and enjoyable getaway.
Brand New 5bed/6bath Pool W/45 Foot Dockage - Available With 2 More Homes - Florida Keys
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 holiday home is ideally situated within 5km of Crane Point Museum, Marathon Air Museum, and Florida Keys Country Club, also offering easy access to Captain Hooks Marina and the Marathon Visitor Centre.
Sleeping up to twelve guests, the property boasts a fully equipped kitchen, private swimming pool, jacuzzi, terrace, garden, parking, and in-unit laundry facilities, plus a balcony with a Smart TV; a hot tub and barbecue grills are also available on-site.
Palm Cottage - Sleeps Up To 4 People - Florida Keys
9.8 57 reviews

Palm Cottage - Sleeps Up To 4 People

cottage, Cudjoe Key
Palm Cottage, a two-bedroom holiday home in Summerland Key, is situated within 2km of Florida Keys Beaches, Crab Key, and Pye Key, offering easy access to these attractions and the Coupon Bight Aquatic Preserve within 10km.
This 45-square-metre self-catering property sleeps four guests and boasts a private patio, swimming pool, garden, and fully equipped kitchen including a washing machine; free Wi-Fi is also provided.
Flamingo Cottage - Sleeps 2 Adults And 2 Children - Florida Keys
9.8 49 reviews

Flamingo Cottage - Sleeps 2 Adults And 2 Children

cottage, Cudjoe Key
The Flamingo Cottage is located in Summerland Key, a short walk from a local tiki bar and a 40km drive to Key West. This cottage has received excellent ratings from previous guests.
The cottage has one bedroom and one bathroom, sleeping up to four guests. It offers a private space with a full kitchen, a shared outdoor pool, a covered patio with a gas grill, and a picnic area.
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