Florida Keys Vacation Rentals, Florida Keys Home Rentals

342 Rentals

List Map
1  2  3  4  5 
Marathon Florida Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Marathon Home

Private island, on ocean side of Marathon! 3 bedroom, 2 bath & 21- ft Carolina skiff. Entire island...

$929 - $1,143 / nt

Key West Florida Vacation Rentals - Villa

6BR / 7BA - Sleeps 16 - Key West Villa

Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart...

$1,143 - $2,000 / nt

Marathon Florida Vacation Rentals - Home

4BR / 4BA - Sleeps 10 - Marathon Home

Enjoy the family and friends at this home with pool, 100' fishing dock with good fishing (right on the...

$400 - $785 / nt


2BR / 2BA - Sleeps 6 - Key Largo Home

Enjoy the real Keys atmosphere. Large (40’ by 16’) screened porch area, complete with kitchen (including...

$65 - $89 / nt

Grassy Key Florida Vacation Rentals - Villa

3BR / 2.5BA - Sleeps 8 - Grassy Key Villa

An attractive house with heated pool/spa, boat dock & beach, in a unique tucked away, completely private...

$229 - $400 / nt

4 Reviews
Long Key Florida Vacation Rentals - Home

2BR / 2BA - Sleeps 9 - Long Key Home

Huge Master Bedroom With View Of Beach And Large Balcony, Refrigerator And Microwave And Bar In 2nd...

$243 - $300 / nt

6 Reviews
view from the 2nd floor balcony

5BR / 3BA - Sleeps 16 - Key Largo Home

Have you ever been in paradise? If not, this is the closest you will ever be, wake up to a beautiful...

$500 / nt

24 Reviews

2BR / 2BA - Sleeps 4 - Key Largo Home

Absolutely adorable.. Ocean access - great boating - fantastic fishing and diving snorkel and scuba!...

$150 / nt

Relaxing nights in elegance soothe the soul !

3BR / 1BA - Sleeps 5 - Key Largo Cottage

Sit back and relax under a coconut tree while watching a great sunset on our sandy private community...

$60 / nt

Ocean View from the balcony

6BR / 6BA - Sleeps 22 - Tavernier Home

This three story house, with a breathtaking view , sits on the edge of the Atlantic Ocean with no end...

$567 / nt

1 Review
Summerland Key Florida Vacation Rentals - Home
Bob & Larisa

4BR / 3BA - Sleeps 8 - Summerland Key Home

Welcome Tropical Villa which is a large home on a clear, flow through swimming canal. With 65 feet of...

$250 - $365 / nt

Pool and beach area with hammock and two person kayak.

4BR / 4BA - Sleeps 8 - Summerland Key Home

Upscale 4 BR/ 4 BA home on the water. Located on a quite cul- de- sac, the property has very lush,...

$250 / nt

1 Review
Marathon Florida Vacation Rentals - Home

1BR / 2BA - Sleeps 4 - Marathon Home

Spectacular view from our open water one bedroom, home. Located on deep canal and private bay front...

$129 / nt

Key Largo Florida Vacation Rentals - Home

5BR / 3.5BA - Sleeps 12 - Key Largo Home

Escape to your own private paradise nestled in one of the most picturesque bay coves in all of Key Largo...

$275 - $475 / nt

1 Review
Marathon Florida Vacation Rentals - Home

2BR / 2BA - Sleeps 4 - Marathon Home

Spend your Vacation right on the Ocean in this 2 bedroom 2 bath Ocean Cottage! We are ground level,...

$222 - $236 / nt

11 Reviews
Marathon Florida Vacation Rentals - Home

3BR / 2.5BA - Sleeps 6 - Marathon Home

High- end Estate overlooking tranquil "Bonefish Flats" in picturesque Marathon. Brand new, Designer...

$350 - $408 / nt

12 Reviews
Islamorada Florida Vacation Rentals - Home

8BR / 5.5BA - Sleeps 16 - Islamorada Home

The Florida Keys Largest, Most Prestigious Vacation Rental Home Available! ! Come stay in your own...

$536 - $858 / nt

Key West Florida Vacation Rentals - Condo

2BR / 2.5BA - Sleeps 6 - Key West Condo

"Tee By The Sea" Vacation Rental (we Include 8 Bikes Free For Our Guests! ! ! ) If You Love... Golf,...

$250 - $450 / nt

3 Reviews
Marathon Florida Vacation Rentals - Condo

3BR / 2BA - Sleeps 8 - Marathon Condo

Bird of Paradise Condo is a tropical three bedroom condo directly on the ocean - BEACH FRONT! Enjoy...

$285 / nt

Key Largo Florida Vacation Rentals - Home

7BR / 5BA - Sleeps 24 - Key Largo Home

This magnificent custom built home is three stories and huge 4, 468 sq ft.. It includes 7 bedrooms,...

$600 / nt

5 Reviews
Marathon Florida Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Marathon Home

This Brand New water front home offers amazing retreat from the hustle & bustle of daily life. It’s...

$210 - $239 / nt

4 Reviews
Key West Florida Vacation Rentals - Condo

2BR / 2BA - Sleeps 6 - Key West Condo

Decorator furnished two bedroom, two full bath condo in Key West, Florida. Only a five minute drive...

$259 / nt

Key West Florida Vacation Rentals - Yacht
Chris & Steph

1BR / 1BA - Sleeps 2 - Key West Yacht

Ever watch Captain Ron? Remember the classic sailboat? Want a unique Keys experience? Romantic, private...

$175 - $300 / nt

1  2  3  4  5 

Florida Keys Travel Tips

The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Made up of Key Largo, Islamorada, Marathon, Key West, and Big Pine Key and the lower keys, these islands have plenty of family-friendly activities. The best way to visit this beautiful area is by choosing to stay in vacation rentals by owner. Florida Keys tourists can choose from a variety of different sized properties designed to make your time in the Keys comfortable and memorable. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price. Your entire family will love exploring the islands and coming home to a private, spacious home or condo.
Beaches and Parks
While staying in one of the area's beautiful vacation rentals, Florida Keys tourists can enjoy a leisurely day at one of the best parks in the nation. These are just a few of the Keys most popular destinations:
  • John Pennekamp Coral Reef State Park is the oldest underwater park in the world. Located in Key Largo, families can explore the 47 campsites located on 67,845 acres, split between land and underwater areas. Nature trails, beaches, kayak and canoe rentals, and glass-bottom boat tours are available.
  • Everglades National Park has many fun activities for families. Kids can become Junior Rangers or go on a wildlife hike.
  • Bahia Honda State Park is known for its beautiful beaches and crystal clear water. Visitors can book a snorkeling tour online and enjoy over an hour of snorkeling in the Looe Key National Marine Sanctuary, where swimmers will explore the gorgeous Elkhorn and Star coral.
Things to Do
The Keys have plenty of fun things to do for every activity level. Families who enjoy the outdoors can take advantage of the wide availability of Florida Keys condo rentals and stay right on the beach!
  • Fishing enthusiasts visiting the Florida Keys will be very excited to hear that Islamorada is known as the sport fishing capital of the world, offering a variety of game fish.
  • Water sports are also very popular in the Keys. Hang gliding, parasailing, kayaking, and paddle boarding are great choices for adventurous families.
  • Swimming with dolphins is a unique experience that every tourist of the Florida Keys should try! Through Dolphins Plus in Key Largo, visitors can go on a structured or natural swim with the dolphins or visit the sea lions through the Sea Lion Encounters program. In Key West, Theater of the Sea offers a wonderful opportunity to swim with dolphins, sea lions, and rays. Kids will have a blast learning about these delightful creatures.
Local History
While staying in one of the area's many vacation rentals, Florida Keys visitors may want to learn a little about the history of these breathtaking islands.
  • Ernest Hemingway Home and Museum is a must for literature enthusiasts. Located in Key West, this historical landmark was Hemingway's home from 1931 to 1939, and the place in which he penned some of his most-loved work.
  • The Florida Keys Eco-Discovery Center is sure to be a hit with the kids. Housing over 6,000 square-feet of interactive exhibits, this museum is a great way to introduce kids to underwater and wildlife ecosystems. And admission is free!
Sightseeing Tours are one of the best ways to learn about the islands. Glass-bottom boat rides, sunset tours, and dinner cruises are all available. Remember to reserve your spot online ahead of time to save on ticket prices.
Fun With Kids
While vacationing in the Florida Keys, rental homes leased by owner are a great choice for families with a few kids who need a little extra space. Florida Keys rental homes are a much better choice than hotels, because families will have a cozy home base to return to after a day of sightseeing. Some of the top activities for kids are:
  • The Key West Butterfly and Nature Conservatory was voted the #1 attraction in Key West by TripAdvisor and People's Choice Awards. Take a stroll through the conservatory, which houses between 50 and 60 species of plants, waterfalls, colorful birds, and of course--butterflies.
  • The Conch Tour Train is a fun way to see Key West with the kids. In operation since 1958, the 90-minute tour will take you through all of the island's most popular attractions.
  • Tropic Cinema has been named "Best Florida Cinema" by Florida Monthly magazine for four consecutive years. This landmark theater screens Hollywood blockbusters, documentaries, and foreign films.
Click for larger map
Show big map »
  • Price

  • Bedrooms


  • Amenities

    • Show More...