Florida Keys Vacation Homes

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Vacation Homes in Florida Keys

Don't see what you're looking for?
See all available properties in Florida Keys
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Florida Keys

    Hawks Cay Resort

    Hawks Cay Resort

    61 Hawks Cay Blvd, Marathon, FL
    8/10 Very Good! (1,000 reviews)
    Isla Bella Beach Resort & Spa

    Isla Bella Beach Resort & Spa

    1 Knights Key Boulevard, MM 47, Marathon, FL
    9/10 Wonderful! (1,002 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    8.8/10 Excellent! (1,203 reviews)

Florida Keys Vacation Homes

Book vacation homes in Florida Keys
Next time you take a group getaway top Florida Keys, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Florida Keys vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Florida Keys vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Florida Keys; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Florida Keys rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Florida Keys is sure to be a winner.

Florida Keys Vacation Homes essential information

Accommodation
1043 Vacation Homes
Lowest Price
Highest Price
Popular accommodation
The Hammocks at Marathon, FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays, KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25, New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities, WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656, Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water, Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks