Lower Florida Keys Cottage Rentals & Holiday Homes
Find the best cottages in Lower Florida Keys - We found 206 exact matches
About Lower Florida Keys Luxury Rental on Trippy Mates
Searching for cottages to rent near Lower Florida Keys? Trippy Mates features more than 206 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 Lower Florida Keys 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. Trippy Mates’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Lower Florida Keys.
Are you planning to travel to the lakeside, beach, or mountain area? Trippy Mates’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.
Trippy Mates boasts of 206 holiday cottages and places to stay in Lower Florida Keys. The site provides unique Airbnb, VRBO, Trippy Mates-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 Lower Florida Keys Cottage Rentals
What are the top rated Cottage Rentals in Lower Florida Keys?
There are a lot of options in Lower Florida Keys. If you plan on staying in the Lower Florida Keys area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Lower Florida Keys:
- 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!
- Beautiful Cottage & Amenities in Gated Community
- ~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
- Living Life Dockside
- Canal front with open water views in Venture Out - Lot 529
- Old Town cottage
- Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
- Ann Street Gardens - Downtown Key West
How much does it cost to rent a cottage in Lower Florida Keys?
The average cost for a cottage rental in Lower Florida Keys is $462 per night. Trippymates has a wide list of great cottages near Lower Florida Keys that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Lower Florida Keys that allow pets?
Yes, here are the top cottage rentals in Lower Florida Keys 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!
- Private Oceanfront Cottage with dockage, pool just minutes to Key West!
See all pet-friendly vacation rentals in Lower Florida Keys on Trippymates
Do you have any rental cottages in Lower Florida Keys that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Lower Florida Keys to find one that works for you.
Are there quality cottages in Lower Florida Keys that have indoor swimming pools?
As of 2026, the data from Trippymates shows that there are Over 206 private swimming pools or cottages with indoor pools in the Lower Florida Keys area along with other great amenities.
