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Discover Your Perfect Florida Keys Cottage Rentals

Florida Keys Cottage Rentals

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9.4 (132 Reviews)
Bed & Breakfast
Andrews Inn & Garden Cottages
  • Air Conditioner
  • Parking
  • Pool
View Availability
More Top-Rated Cottage Rentals in Florida Keys Area

Why Choose Rent By Owner for your Florida Keys Cottage Rentals?

What makes our Cottage Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Florida Keys Cottage Rentals

Where are the best neighborhoods to stay in Florida Keys?

For an authentic Florida Keys experience, consider staying in neighborhoods near Key Largo or Islamorada, where you can enjoy tranquil surroundings and convenient access to the area's natural beauty. These areas offer a perfect blend of relaxation and adventure, making them ideal for your next getaway. Exploring the local ambiance from these friendly neighborhoods will ensure a memorable stay in the Florida Keys.

Key West Historic District

In this vibrant area, you can immerse yourself in the historic charm and lively culture that define the region. It’s an ideal choice for travelers seeking authentic experiences near charming cottages.

View 2409+ Rentals in Key West Historic District

Old Town

Known for its picturesque streets and colorful architecture, this neighborhood offers a relaxed atmosphere just moments from cozy cottages perfect for exploring local sights.

View 2371+ Rentals in Old Town

Sunset Key

This tranquil island provides a peaceful retreat with stunning sunset views, making it an excellent spot to find private cottages away from the bustling areas.

View 3595+ Rentals in Sunset Key

Downtown

Centering around lively nightlife and shops, this part of the region places you close to convenient cottages and the energetic pulse of the area.

View 992+ Rentals in Downtown

Uptown - Upper Duval

Offering a quieter alternative to the main street, this neighborhood features charming cottages nestled in a welcoming community setting.

View 761+ Rentals in Uptown - Upper Duval

Key Largo Village

Here, you’ll find a laid-back atmosphere filled with opportunities for outdoor activities, complemented by cottages that provide comfort and convenience in a tropical setting.

View 34+ Rentals in Key Largo Village

Bahama Village

Rich in cultural heritage, this neighborhood offers a unique ambiance with access to charming cottages immersed in local traditions and vibrant community life.

View 92+ Rentals in Bahama Village

New Town

This emerging area presents a blend of modern conveniences and relaxed surroundings, perfect for discovering comfortable cottages in a developing part of the region.

View 107+ Rentals in New Town

Best Times to Visit Florida Keys

When should you plan your Cottage Rentals stay?

Choosing the ideal time to vacation here can enhance your experience, as this destination offers different attractions and weather patterns throughout the year, so planning your stay during the optimal season ensures you enjoy the best of what the region has to offer for a memorable getaway.

Peak Season Highlights

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Winter (December to February)

During the winter months, the region experiences its busiest season, attracting visitors seeking warm weather and outdoor activities. This is the ideal time for you to enjoy the vibrant atmosphere and beautiful coastal scenery.

Average Temperature Daytime: 75°F - Nighttime: 65°F
spring
Spring (March to May)

Spring is a popular period when travelers flock here for pleasant temperatures and blooming landscapes. Booking your cottages early ensures a memorable stay amidst the lively seasonal events.

Average Temperature Daytime: 78°F - Nighttime: 70°F

Off-Season Highlights

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Summer (June to August)

In the summer, fewer visitors visit during the hottest months, which can offer you more secluded access to the area's natural beauty. It's a good opportunity to find deals on cottages while enjoying the warm waters.

Average Temperature Daytime: 88°F - Nighttime: 78°F
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Fall (September to November)

Autumn sees a dip in tourism as the weather cools slightly, providing a quieter experience. This is an excellent time for you to explore the region with less crowd while still benefiting from mild temperatures.

Average Temperature Daytime: 82°F - Nighttime: 72°F

Weekly Weather Forecast for Florida Keys

How to Book Your Florida Keys Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Florida Keys

More Top-Rated Cottage Rentals in Florida Keys Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy private outdoor spaces such as patios or decks perfect for relaxing and dining al fresco.
  • Take advantage of waterfront access or stunning views from your outdoor living area.
  • Make the most of available BBQ grills to host cookouts in a scenic setting.
  • Relax by a private or shared swimming pool that offers refreshing relief from the Florida sun.
  • Experience outdoor showers designed to keep you refreshed after sandy beach days.
  • Utilize lush landscaped gardens and tropical plants for an authentic regional ambiance.
  • Access covered porches or verandas ideal for enjoying gentle breezes and sunset views.

Top Attractions Around Florida Keys

What attractions are nearby?

In this destination, you can enjoy a variety of activities such as exploring vibrant marine life through snorkeling or diving, relaxing on pristine beaches, and discovering charming local shops and eateries-all just moments from your cozy cottages and offering an authentic taste of the region's laid-back coastal vibe.

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Family Activities

  • Snorkeling and Water Adventures: Explore the vibrant underwater world by snorkeling in popular spots, where you can observe colorful marine life and coral reefs just off the coast.
  • Visit the Florida Keys Eco-Discovery Center: Engage your family with interactive exhibits and educational programs focused on the region's unique ecosystem and marine conservation efforts.
  • Relax on Family-Friendly Beaches: Spend your days lounging on sandy shores that are perfect for building sandcastles and enjoying safe swimming conditions suitable for children.
  • Explore Marine Parks and Wildlife Sanctuary: Discover local wildlife through guided tours and nature walks in protected areas that highlight the area's rich biodiversity.
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Adult Activities

  • Snorkeling and Diving: Explore vibrant coral reefs and marine life in the clear waters of the Florida Keys, making it an ideal activity for underwater enthusiasts seeking an unforgettable experience.
  • Fishing Excursions: Enjoy world-class fishing opportunities here, whether you're casting a line from the shore or taking a boat out into the open waters, perfect for avid anglers.
  • Sunset Cruises: Experience breathtaking sunsets on a relaxing cruise, offering stunning views and a romantic atmosphere along this scenic coastal region.
  • Wildlife Watching: Discover diverse wildlife by visiting local parks and refuges, where you can observe unique bird species and marine creatures native to this area.

Other Places to Stay in Florida Keys, FL

Lower Florida Keys
Explore 3,909 Properties
Key West
Explore 3,093 Properties
Key West Historic District
Explore 2,409 Properties
Old Town
Explore 2,371 Properties
Duval Street
Explore 1,753 Properties
Marathon
Explore 1,603 Properties
Pretty Joe Rock
Explore 1,485 Properties
Key Largo
Explore 1,370 Properties
Downtown
Explore 992 Properties
Islamorada
Explore 896 Properties
Lower Keys
Explore 867 Properties
Upper Matecumbe Key
Explore 793 Properties
More Places to Stay Near Florida Keys

Florida Keys Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: To maximize your time here, organize your activities beforehand and consider booking local tours or water sports through your cottages provider for convenience.
  • Explore Local Cuisine: Indulge in the region's fresh seafood and authentic dishes by dining at highly-rated spots near your cottages to truly experience the area's culinary delights.
  • Discover Hidden Beaches: Take advantage of the area’s lesser-known beaches for peaceful relaxation and unobstructed views, providing a perfect escape during your stay.
  • Utilize Local Transportation: Make use of available transportation options or rent bikes to easily explore the scenic surroundings and access popular attractions with ease.

Transportation Options

  • Car Rentals: Renting a car provides you with the flexibility to explore the islands at your own pace, making it easier to access secluded beaches and local attractions from your cottage.
  • Ferries and Water Taxis: This region’s water-based transportation allows you to enjoy scenic rides between key islands and offers a convenient way to reach your chosen cottages in remote areas.
  • Public Buses: The local bus system offers an economical option for getting around, connecting popular spots within the area while providing a stress-free travel experience to your accommodations.
  • Bike Rentals: For a more leisurely experience, biking is an eco-friendly choice that lets you immerse yourself in the natural beauty of the islands while comfortably reaching nearby cottages.

Local Customs Options

  • Respect for the Marine Environment: Locals here take pride in preserving the pristine waters, so you’ll notice a strong emphasis on eco-friendly practices and marine conservation efforts.
  • Celebration of Seafood Cuisine: Enjoy the region’s rich culinary traditions by participating in local seafood festivals and savoring dishes that highlight fresh, regional catches.
  • Fisherman’s Hospitality: Visitors often experience warm welcomes rooted in the area's long-standing fishing heritage, reflecting the community’s friendly and laid-back spirit.
  • Respect for Island Customs: Here, respecting quiet hours and maintaining cleanliness are valued customs that help preserve the tranquil atmosphere of this tropical destination.

Frequently Asked Questions About Florida Keys Rental Cottages

1. What are the top Cottages in Florida Keys?

There are a lot of options in Florida Keys. If you plan on staying in the Florida Keys area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Florida Keys:

2. How many Cottages are available in Florida Keys?

Currently, the total number of properties listed by RBO in 2026 is over 311 in the Florida Keys area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Florida Keys. 

3. What is the cancellation policy for cottages in this area?

The cancellation policy varies by listing. You should review the specific property's cancellation terms on the listing page or contact the owner directly for detailed information.

4. Are there any specific requirements or restrictions when booking a cottage here?

Many properties have unique requirements or restrictions, such as minimum stay durations or occupancy limits. Please check the individual listing details or reach out to the owner for clarification.

5. How do I confirm my booking and what are the payment options available?

Booking confirmation and payment methods are outlined on each listing. You can typically complete your reservation online using secure payment options, or contact the owner directly if you need assistance.

6. Are pet-friendly cottages available in this region?

Some listings accommodate pets, but availability varies. Review each property's pet policy on its page or contact the owner to confirm if bringing your pet is permitted.

7. What amenities should I expect at cottages in this destination?

Amenities differ depending on the property, but common features include kitchens, outdoor spaces, and Wi-Fi. Check the full list of amenities on the specific listing to ensure it meets your needs.

More Rentals You May Like Near Florida Keys

10.0 (112 Reviews)
Cottage
Oceanfront Private Cottage!
  • Air Conditioner
  • Parking
  • Pet Friendly
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More Top-Rated Cottage Rentals in Florida Keys Area