Key West Cottage Rentals & Holiday Homes
Find the best cottages in Key West - We found 131 exact matches
About Key West Luxury Rental on Orlando Vacation Rentals
Searching for cottages to rent near Key West? Orlando Vacation Rentals features more than 131 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 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. Orlando Vacation Rentals’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Key West.
Are you planning to travel to the lakeside, beach, or mountain area? Orlando Vacation Rentals’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.
Orlando Vacation Rentals boasts of 131 holiday cottages and places to stay in Key West. The site provides unique Airbnb, VRBO, Orlando Vacation Rentals-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 Cottage Rentals
What are the top rated Cottage Rentals in Key West?
There are a lot of options in Key West. If you plan on staying in the Key West 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:
- 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
- The Dancing Rooster: 2 Blocks from Duval in Old Town.
- Colony Sunset- Bright and airy cottage in the heart of old town Key West
- A Touch of Bermuda at Truman Annex
- NEW! - The Jolly Rooster CottagenSteps to Duval - Prime and Quiet Location
How much does it cost to rent a cottage in Key West?
The average cost for a cottage rental in Key West is $501 per night. Orlando Vacationrentals has a wide list of great cottages near Key West that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Key West that allow pets?
Yes, here are the top cottage rentals in Key West that allow you to bring your pet:
- "Tranquility " At Ann Street Gardens Steps From Duval
- Andrews Inn & Garden Cottages
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
- Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
See all pet-friendly vacation rentals in Key West on Orlando Vacationrentals
Do you have any rental cottages in Key West that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Key West to find one that works for you.
Are there quality cottages in Key West that have indoor swimming pools?
As of 2026, the data from Orlando Vacationrentals shows that there are Over 131 private swimming pools or cottages with indoor pools in the Key West area along with other great amenities.
