Holiday Rentals in Summerland Key
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Check rental availability in Summerland Key
Holiday Rentals in Summerland Key

Old Florida Style, wrap around porch, boat basin for dockage, open water

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Waterfront Home

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Canal front, dockage, 2 bedroom, 2 bath

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Private Secluded Ocean View & Pool Near Key West

Comfortable Waterfront Vacation Rental

20 MINUTES TO KEY WEST , BOATERS PARADISE

OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season

A Tropical Luxury Getaway, Your own private resort!!

waterfront cottage near key west, sleeps 6

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Other types of properties in Summerland Key you may be interested in

Parmer's Resort
Holiday Accommodation Summerland Key
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Summerland Key are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Summerland Key itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Summerland Key holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Summerland Key, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Summerland Key with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.