Flamingo Cottage Rentals & Holiday Homes
Find the best cottages in Flamingo - We found 81 exact matches
About Flamingo Luxury Rental on Surfside Vacation Rental
Searching for cottages to rent near Flamingo? Surfside Vacation Rental features more than 81 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 Flamingo 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 Flamingo.
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 81 holiday cottages and places to stay in Flamingo. 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 Flamingo Cottage Rentals
What are the top rated Cottage Rentals in Flamingo?
There are a lot of options in Flamingo. If you plan on staying in the Flamingo area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Flamingo:
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- Middle Florida Keys Bayfront with Sailboat or boat slip included
- 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!
- Oceanfront Cottage With Stunning Pool & Dockage in Islamorada
- Blue Isle Gem II- Gulf of America in the front yard
- Marina View Cottage at Key Largo
- Water Front Home With Pool and Dock Three min From Atlantic Ocean
- WATERFRONT COTTAGE W/MOTHER IN LAW TREETOP SUITE &SAILBOAT OR BOAT SLIP INCLUDED
How much does it cost to rent a cottage in Flamingo?
The average cost for a cottage rental in Flamingo is $398 per night. Surfsidevacationrental has a wide list of great cottages near Flamingo that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Flamingo that allow pets?
Yes, here are the top cottage rentals in Flamingo that allow you to bring your pet:
- Carpe' Diem Heart of the Fl. Keys Specials
- Key Lime Cottage in the heart of Islamorada
- Tropical Cottages
- Keys Waterfront Half-Duplex, Ocean side 37' Dock,
See all pet-friendly vacation rentals in Flamingo on Surfsidevacationrental
Do you have any rental cottages in Flamingo that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Flamingo to find one that works for you.
Are there quality cottages in Flamingo that have indoor swimming pools?
As of 2026, the data from Surfsidevacationrental shows that there are Over 81 private swimming pools or cottages with indoor pools in the Flamingo area along with other great amenities.
