Monroe County Cottage Rentals & Holiday Homes
Find the best cottages in Monroe County - We found 321 exact matches
About Monroe County Luxury Rental on Surfside Vacation Rental
Searching for cottages to rent near Monroe County? Surfside Vacation Rental features more than 321 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Monroe County have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Surfside Vacation Rental’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Monroe County.
Are you planning to travel to the lakeside, beach, or mountain area? Surfside Vacation Rental’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Surfside Vacation Rental boasts of 321 holiday cottages and places to stay in Monroe County. The site provides unique Airbnb, VRBO, Surfside Vacation Rental-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Monroe County Cottage Rentals
What are the top rated Cottage Rentals 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 Cottage Rentals in Monroe County:
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- Middle Florida Keys Bayfront with Sailboat or boat slip included
- 2 bedroom & 25' Boat Dock ~ Waterfront Atlantic Side & PrivateTiki dining, bikes
- Ann Street Tranquility: A cozy and peaceful cottage
- 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
- Experience paradise at Green Cottage, a charming 2-bedroom oceanfront retreat in Islamorada!
- Kampground Waterfront Paradise/w Private Dock, BBQ and Kayaks
- Key Largo Waterfront Paradise w/Kayaks, Private Dock & BBQ
- CORAZON: Old Town MONTHLY - Private Pool - LARGE 2BD/2.5BA - RealKeyWest
How much does it cost to rent a cottage in Monroe County?
The average cost for a cottage rental in Monroe County is $413 per night. Surfsidevacationrental has a wide list of great cottages near Monroe County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Monroe County that allow pets?
Yes, here are the top cottage rentals in Monroe County that allow you to bring your pet:
- "Tranquility " At Ann Street Gardens Steps From Duval
- Key Lime Cottage in the heart of Islamorada
- Casita de Catherine by Avantstay 1 Block to Duval St w/Hot Tub!
- Private Oceanfront Cottage with dockage, pool just minutes to Key West!
See all pet-friendly vacation rentals in Monroe County on Surfsidevacationrental
Do you have any rental cottages in Monroe County that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Monroe County to find one that works for you.
Are there quality cottages in Monroe County that have indoor swimming pools?
As of 2026, the data from Surfsidevacationrental shows that there are Over 321 private swimming pools or cottages with indoor pools in the Monroe County area along with other great amenities.
