COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Vacation Rentals & House Rentals in Florida Keys

Updating...

age 0-16
834 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

834 house rentals

Bayfront Vacation Home Beach House Rental Bayside Steps from the Water

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 9

“Abbsolutly Fantastic !!” This is our second year staying a week. Can not say enough about how much we love this house. It's not often you ca stay somewhere for this amount of time and feel like you are are coming home when you arrive for vacation. The house has all the amenities you will need to include fishing rods and 1 and 2 person Kayaks. toys for the kids etc. The location is also great near restaurants, marinas etc. The only complaint once you stay here you are hooked ! We were already ready to book for next year immediately after this vacation. If you want a stress free place for a vacation this is it.

Price per night from

$458

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 2 hours 34 minutes

Price per night from

$297

CasaAzul Waterfront (Dock)

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$687

Dockside Condo and Boat

Key Largo apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$401

A Castle on An Island Your Santuary Retreat Key West Sleeps up to 20

Key West house

8 bedrooms / 8 bathrooms / sleeps 20

Responds fast! avg. 2 hours 35 minutes

Price per night from

$1,799

Bayfront Vacation Home Cottage Rental Bayside Beach *Renovated 2019*

Key Largo cottage

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing!” This place is the best. We will definitely return. The cottage had everything we needed, plenty of dockage for our boats, kids loved the kayaks, and spectacular views. Martha was wonderful to work with and made sure we had everything we needed.

Price per night from

$258

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 49 minutes

Price per night from

$401

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 26 minutes

Price per night from

$257

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Islamorada house

4 bedrooms / 2 bathrooms / sleeps 14

Price per night from

$401

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 35 minutes

Price per night from

$2,199

CARIBBEAN SOUL SAILING CHARTER Bayfront 2 BR cottage w/ 23 foot Sailboat or dock

Conch Key cottage

2 bedrooms / 1 bathroom / sleeps 6

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

Price per night from

$327

Reef Resort - Peaceful Getaway 204

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

Price per night from

$271

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 49 minutes

Price per night from

$401

Truman Annex-Steps to Famous Duval Street

Key West townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$393

SANCTUARY IN PARADISE

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

“What Florida dreams are made of” Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than my dreams could have asked for! We were tremendously blessed to have had the opportunity to share this paradise! Private, gated estate with coral wooded hammocks to stroll through, palm trees clicking in the breeze, flocks of ibis that grazed through the lush green yard that ended at the private water front. Orchids blooming in the trees welcomed us to the hammocks where we had our morning coffee to stunning colored sunrises. It had everything: super clean Keys styled house with a cute kitchen (that saved us on meal expenses), bedrooms and bathrooms that were perfect size and accommodations, and wifi. It was quiet yet welcoming to my kids. We kayaked and swam on Christmas morning! The hosts were gracious and really made us feel as we were family. It was a Christmas we will always cherish. "Give and it will be given to you. A good measure, pressed down, shaken together and running over, will be poured into your lap." Luke 6:38 Truly, after giving us the chance to come share your slice of heaven, our cup runneth over.

Responds fast! avg. 1 hour 51 minutes

Price per night from

$573

Pools, Jacuzzis, Rec Room, Gym, 24/7 security! Stay at Mariner's Club 606!!

Key Largo townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$745

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

Price per night from

$320

Sleeping Room, Private Entrance and use of RV Park Bathrooms, Beach and Marina

Key Largo private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$121

Spacious 1 Bedroom, Full Kitchen, Central Air, Beach, Marina and Docks

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 3

“Tranquil and friendly” This was a place we found after months of searching and having another owner cancel out on us. We came in with a pre judgement of the place and BOY were we wrong. Everyone is super nice, everyone there(employees and guests) are very caring and friendly. The apartment was very comfy and well equipped, although anextra blanky or throw would have been nice to have for the sofa lounging. We are only 4 days into it but all is great!

Price per night from

$281

Large Home near Beach & Key West

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 3 hours 9 minutes

Price per night from

$457

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$344

Keys Kottage

Islamorada villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$269

Ocean Vista

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$343

Beautiful Home on the Water

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 3 minutes

Price per night from

$344

Price per night from

$304

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,718

Key West Suites Hotel unit 201

Key West apartment

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$343

Bayfront Cottage with Bay Front Screen Porch, Central Air, Beach and Marina

Key Largo cottage

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$373

Private Heated Pool, New Boat Dock and Ready Enjoyment!

Key Colony Beach house

2 bedrooms / 1 bathroom / sleeps 4

“Keys” This house was awesome!! My family really enjoyed staying here! We plan on booking this house for next year already. It has everything you need! And it is fully renovated all throughout! We are happy we were able to find this!!

Price per night from

$263

Bayfront Vacation Home Villa Rental Bayside Beach View

Key Largo villa

2 bedrooms / 2 bathrooms / sleeps 6

“FANTASTIC” WE LOVED EVERY BIT OF OUR STAY !! Pretty much as described private beach deep water dock . Beautiful views !! The property is shared but the main house is owned by the same couple. There is plenty of room and lots of toys to play with. ( kayaks, fishing gear, sand toys) we will be back !!!

Price per night from

$229

Paraidise with or witout boat

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 25 minutes

Price per night from

$315

Discover the Charm of Island Living

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 10 minutes

Price per night from

$229

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 3 hours 28 minutes

Price per night from

$315

BAYSIDE CONDO WITH BOAT

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

“Very friendly and relaxing atmosphere!” My wife and I were really pleased with our trip. So relaxing and everyone in the area were so friendly and helpful. Thank you Jay, Sander and the crew at Sail Fish Scuba. Love having the boat to go and explore the area. Will definitely do it again!

Price per night from

$373

The Eagle's Nest

Tavernier bungalow

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$155

Blue Marlin

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$160

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$243

Meagan's Beach House - Bayfront Home with Spectacular Sunrise and Sunsets

Key Largo house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$287

Viewing 38 of 834
rentals in Florida Keys

×

About Florida Keys

Florida Keys, FL, including the islands of Key West, Key Largo, Islamorada, Marathon Key and Big Pine Key offers the perfect mix of family beach fun and peaceful vacation relaxation. Spend your days strolling one of the many boardwalks, or swim, snorkel, and kayak in the pristine Gulf. After a long day, retreat back to your vacation rental home at night, escape the crowds, and watch the sunset across the Gulf from your personal porch or deck. With your own private tennis court and pool, luxuries that many rentals offer, you can have a great time without even leaving your vacation home.

Wake up to the sound of waves rolling in and the scent of the salty ocean air, then walk just minutes to the beach for great boardwalk shopping, dining, and entertainment. Truly escape the winter chill by heading to the southernmost point in the United States, Key West, Florida. Take U.S. Highway 1, known to locals as "The Overseas Highway" to get there, and enjoy the breath-taking natural beauty of the ocean scenery and wilderness that borders the road.

Here are a few additional suggestions for your trip to the Florida Keys:

  • Visit the Key West Butterfly & Nature Conservatory: Key West is home to a magnificent array of butterflies from South America, Africa, and Southeast Asia. This Conservatory emphasizes the importance of wildlife preservation, offering group tours, unique films, and resident rainforest birds guaranteed to ignite your love for wildlife.
  • Swim with the dolphins: Key West is known for its dolphin friendly environment and facilities that offer guests the opportunity to swim and play with these amazing animals.
  • Explore The Harry S. Truman Little White House: Established in 1890 as a command center during the Spanish American War, this house was later used as a means of escape during the Cold War. For years, presidents relaxed and restored body and mind here while dealing with war threats. The site is now a living history museum.
  • Sleep under the stars: Spend a night under the legendary stars of Key West. Florida Keys campgrounds are plentiful, and Florida Keys camping can also happen at sea. Charter a boat and drift off with the night sky above and the ocean below.
  • Take a sunset dinner cruise: Gourmet dinner cruises to Florida Keys' destinations are widely available. Nothing is more romantic than raising a glass on a luxury sailboat as the sun sets over the Atlantic.
  • Take a charter fishing trip: An experienced outfitter can provide the boat and equipment you need to pursue deep water species like marlin and swordfish.

Whether you're here for a Florida Keys honeymoon, a family reunion, or a vacation getaway with friends, you'll easily find a perfect vacation rental with all the amenities you need to relax in style. Stay in a charming beach condo close to the restaurants and nightlife or rent an elegant villa with a balcony and stunning views of the ocean. You may also want to make some time during your vacation to visit nearby destinations like Naples or Marco Island.

Top Destination reviews

Island Hideaway
Key West

It was perfect for us. Only thing was the washer and dryer were persnickety. We each had our own space which was nice. … see more
Bayfront Vacation Home Villa Rental Bayside Beach View
Great Rental Property

My family and I had a great time at this rental property, and would recommend it. House was nice and roomy for a family of four. Great fishing off of the dock. Beautiful sunsets. Kayaks on site to use at no additional cost. Owner is very nice. This location will help you relax. We hope to come back soonsee more
Bayfront Vacation Home Cottage Rental Bayside Beach *Renovated 2019*
Perfect

Great house. Very clean and simple. You share the beach and dock with the two other houses in the property but was never an issue. Location is great in Largo. Martha was a great host and very friendly. Will definetly be going back. … see more
Sunshine suit (2/2 apartment)
Nice

It was a great place wit your family .my daughter loved it cause the pool was right on front our building … see more
Paraidise with or witout boat
Fun I. The Keys

The owner was very accommodating. And very willing to work with us in adjusting our reservation as tropical storm Elsa inspired us to adjust our stay date. Living area is nicely decorated. Location is excellent. Marathon's Sombrero Beach is a bike ride away. Recreation trail runs right in front of the house. We brought our boat and enjoyed snorkling at Sombrero reef. Fished at several locations on the Atlantic side. Did lots of tubing on the gulf side. Only down side was the back deck and steps need a bit of attention. We would definitely stay there again.see more
Dolphin Oasis 4bdr/4bth Pool/hot tub 115' dockage
Excellent

Location is great. Especially if you bring your boat. Home is wonderful. Pool was great after long day on the water. Owners have done a great job of making their home accommodating. My family had a wonderful time. Will be back. … see more

Also consider