Key West Historic District Cottage Rentals & Holiday Homes
Find the best cottages in Key West Historic District - We found 111 exact matches
About Key West Historic District Luxury Rental on Romantic Wine Tours
Searching for cottages to rent near Key West Historic District? Romantic Wine Tours features more than 111 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 Key West Historic District 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. Romantic Wine Tours’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Key West Historic District.
Are you planning to travel to the lakeside, beach, or mountain area? Romantic Wine Tours’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.
Romantic Wine Tours boasts of 111 holiday cottages and places to stay in Key West Historic District. The site provides unique Airbnb, VRBO, Romantic Wine Tours-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 Key West Historic District Cottage Rentals
What are the top rated Cottage Rentals in Key West Historic District?
There are a lot of options in Key West Historic District. If you plan on staying in the Key West Historic District area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Key West Historic District:
- Ann Street Tranquility: A cozy and peaceful cottage
- TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet & gated. Pool/Deck/Pet frien
- LAST MINUTE AVAILABILITY! architect designed OASIS in OLD TOWNE on a quiet lane!
- Old Town cottage
- Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
- Ann Street Cottage: A bright and airy home near Duval Street
- Colony Poolside: A charming bungalow near Duval Street
- Pete's Cottages: Twin Cypress cottages steps from Duval
- Pete's East Cottage: Cypress east cottage steps from Duval
- Pete's West Cottage steps from Duval
How much does it cost to rent a cottage in Key West Historic District?
The average cost for a cottage rental in Key West Historic District is $526 per night. Romanticwinetours has a wide list of great cottages near Key West Historic District that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Key West Historic District that allow pets?
Yes, here are the top cottage rentals in Key West Historic District that allow you to bring your pet:
- "Tranquility " At Ann Street Gardens Steps From Duval
- Andrews Inn & Garden Cottages
- Tranquility by Avantstay Close to Duval St w/BBQ & Shared Pool
- Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
See all pet-friendly vacation rentals in Key West Historic District on Romanticwinetours
Do you have any rental cottages in Key West Historic District that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Key West Historic District to find one that works for you.
Are there quality cottages in Key West Historic District that have indoor swimming pools?
As of 2026, the data from Romanticwinetours shows that there are Over 111 private swimming pools or cottages with indoor pools in the Key West Historic District area along with other great amenities.
