Monroe County Cottage Rentals
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Why Choose Rent By Owner for your Monroe County Cottage Rentals?
What makes our Cottage Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Monroe County
When should you plan your Cottage Rentals stay?
Timing your visit to this destination can enhance your experience, as certain seasons offer more favorable weather and activities, making it easier for you to find the perfect cottages and enjoy all that the region has to offer.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its peak season, attracting visitors seeking warm weather and outdoor activities.
Average Temperature Daytime: 75°F - Nighttime: 65°F
Spring (March to May)
Spring enthusiasts flock here in the peak season for pleasant temperatures and blooming scenery, perfect for exploring the region’s natural beauty.
Average Temperature Daytime: 80°F - Nighttime: 70°F
Off-Season Highlights
Summer (June to August)
The summer off-peak period offers quieter surroundings, although it can be hotter and more humid, ideal for those seeking a relaxed experience away from crowds.
Average Temperature Daytime: 88°F - Nighttime: 78°F
Fall (September to November)
Autumn sees fewer visitors, providing a peaceful atmosphere with comfortable temperatures that are ideal for leisurely activities and enjoying the area's natural landscape.
Average Temperature Daytime: 82°F - Nighttime: 72°F
Weekly Weather Forecast for Monroe County
How to Book Your Monroe County 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 Monroe County
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 outdoor swimming pools that provide a refreshing escape during warm days in the region.
- Relax in shaded picnic areas perfect for outdoor dining with family and friends.
- Take advantage of spacious decks or patios for outdoor lounging and sunset viewing.
- Benefit from lush landscaped gardens that add natural beauty to your stay.
- Make use of private or community barbecue grills to prepare meals al fresco.
- Explore well-maintained walking trails or paths surrounding the property for outdoor recreation.
- Experience the tranquility of waterfront access or views, ideal for relaxing or water activities.
Top Attractions Around Monroe County
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of outdoor activities, water sports, and nature excursions that showcase the natural beauty and diverse ecosystem nearby, making it an ideal destination for those seeking adventure and relaxation in the heart of the Florida Keys.
Family Activities
- Snorkeling and Beach Exploration: Discover the vibrant marine life and pristine beaches of the area, perfect for family-friendly snorkeling adventures right from your cottage doorstep.
- Visit to Local Marine Parks: Spend a day exploring marine parks that offer educational exhibits and interactive activities suited for children and adults alike.
- Kayaking Tours: Enjoy paddling along calm waters with guided tours designed for families, providing an engaging way to see the region's natural beauty.
- Wildlife Watching Excursions: Experience the region’s diverse ecosystems by taking wildlife excursions tailored for families, where you might spot dolphins, manatees, or tropical birds.
Adult Activities
- Snorkeling and Diving: Explore the vibrant coral reefs and marine life in the crystal-clear waters, offering an unforgettable aquatic adventure just minutes from your holiday retreat.
- Fishing Excursions: Enjoy a day on the water with guided fishing trips, where you can test your skills or simply relax and take in the scenic views of the region's abundant waterways.
- Key West Day Trip: Embark on a scenic journey to nearby Key West, experiencing its lively arts scene, historic sites, and exceptional dining options for a full day of exploration.
- Luxury Yacht Charters: Charter a luxury yacht to cruise around the islands, offering stunning sunset views and private escapes tailored to your preferences within this coastal area.
Other Places to Stay in Monroe County, FL
Florida Keys
Lower Florida Keys
Key West
Key West Historic District
Old Town
Duval Street
Marathon
Pretty Joe Rock
Key Largo
Downtown
Islamorada
Lower Keys
Monroe County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead To maximize your experience here, research local outdoor adventures and water-based activities that showcase the area's natural beauty.
- Choose a Prime Location Selecting a cottage close to popular beaches or scenic spots will give you more time to enjoy the region’s renowned attractions.
- Explore Local Dining Options Sampling fresh seafood at nearby eateries offers an authentic taste of the area’s culinary scene and adds to your overall visit.
- Pack Smart for the Climate Be sure to bring appropriate attire for the warm, sunny weather typical of this destination to stay comfortable during your stay.
Transportation Options
- Rental Car Services: Rent a vehicle from local providers to explore the area at your own pace and easily access secluded beaches or nearby islands.
- Public Transit: Utilize regional buses that connect key parts of the destination, offering an affordable and eco-friendly way to get around.
- Taxi and Ride-Sharing: Convenient taxi services or ride-sharing options provide flexible transportation for quick trips within the region or to local attractions.
- Boat Rentals: Experience the waterways by renting boats, which is an ideal way to enjoy the scenic coastlines and marine activities unique to this destination.
Local Customs Options
- Respect for Marine Life: You should always observe local guidelines to protect the abundant marine life found in this destination's waters, ensuring a sustainable experience during your stay.
- Local Fishing Etiquette: Engaging in fishing activities here requires understanding and respecting established traditions and regulations to maintain harmony with the community.
- Celebration of Art and Culture: Participating in regional art festivals and cultural events is a cherished custom that offers insight into the area's vibrant community spirit.
- Environmental Conservation: Practicing eco-friendly habits, such as proper waste disposal and minimal disturbance to natural habitats, is highly valued by residents and visitors alike.
Monroe County Cottage Rentals Frequently Asked Questions
1. What are the top Cottages in Monroe County?
There are a lot of options in Monroe County. If you plan on staying in the Monroe County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Cottages in Monroe County:
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
- ~ COPA CABANA ~ Classic Key West cottage just a stone’s throw from the water.
- Charming Bayfront Cottage in Heart of Islamorada with Heated Pool, Deep Dockage, Kayaks & More
- Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More
- ~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
- Kampground Waterfront Paradise/w Private Dock, BBQ and Kayaks
- Truly sitting right on the ocean. Ocean's Edge has forever ocean views.
- CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
- LAST MINUTE AVAILABILITY! architect designed OASIS in OLD TOWNE on a quiet lane!
2. How many Cottages are available in Monroe County?
Currently, the total number of properties listed by RBO in 2026 is over 311 in the Monroe County area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Monroe County.
3. What is the cancellation policy for cottages in this area?
Cancellation policies vary depending on the specific property, so it's important to review the listing details or contact the owner directly to understand the terms and any applicable fees before booking.
4. Are there any additional fees I should be aware of when booking a cottage here?
Additional fees such as cleaning fees, service charges, or taxes may apply. These are typically outlined in the listing details, but reaching out to the owner can provide clarity on any extra costs.
5. Can I bring pets to stay in a cottage in this destination?
Pet policies differ among properties, with some allowing pets while others do not. You should check the individual listing or contact the host to confirm whether pets are permitted during your stay.
6. Is there flexible check-in and check-out times available?
Check-in and check-out times depend on the property’s policies. Some hosts offer flexible options; it’s best to inquire directly with the owner to ensure your preferred schedule fits their availability.
7. What amenities are typically included in cottages in this region?
Amenities can vary but generally include essentials like Wi-Fi, kitchen facilities, and outdoor spaces. To find out about specific amenities, review the property listing or contact the owner for detailed information.
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