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
225 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

225 house rentals

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$288

Match: Private outdoor pool (heated)

All filters match

Price per night from

$287

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 49 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$225

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 1 hour 27 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$568

OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problems. I would highly recommend this rental

Responds fast! avg. 2 hours 3 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$654

NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 51 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$173

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

2 bedrooms / 3 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$344

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 2 hours 52 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$654

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$466

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!!

Travelers’ Choice award

Match: Private outdoor pool (heated)

All filters match

Price per night from

$263

Waterfront luxury Villa (54) with sunset views and boat slip

Marathon villa

3 bedrooms / 3 bathrooms / sleeps 8

“Beautiful condo in a beautiful setting” Sitting on the front porch watching the sunset was one of the highlights of the trip. And the pool was the best we've ever swam in.

Responds fast! avg. 1 hour 43 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,145

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 56 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$2,013

Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 26 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$544

Canal-Side Home w/ Large Private Dock, Covered Patio & Waterfront Pool

Key Colony Beach house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$329

TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$183

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 2 hours 52 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$658

Seaside Place Key West FL 5 Bedroom House 4 Baths

Key West house

5 bedrooms / 4 bathrooms / sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

Responds fast! avg. 3 hours 34 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,442

Big house

Key West house

5 bedrooms / 5 bathrooms / sleeps 12

“Bachelorette in Key West” I rented this house for my sister-in-law's bachelorette weekend in Key West. The house was spacious, clean, and overall the best place I've ever stayed! It was worth every penny!

Match: Private outdoor pool (heated)

All filters match

Price per night from

$700

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Responds fast! avg. 2 hours 52 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$482

Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)

Responds fast! avg. 34 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$637

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$100

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$262

Coco Plum Beach 2 BR/ BA Fantastic Condo

Marathon condo

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$196

MARATHON MAJIC

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$322

Luxurious waterfront home w/panoramic views, pool/spa & dock

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$603

** Fantastic Spring& Summer Stay Downtown walk everywhere **

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$369

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$100

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$418

BEACON REEF 406

Matecumbe Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$100

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$193

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$327

Paradise Beach Sandy Oceanfront

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 58 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,260

7 ROOM NEW VACATIONAL HOME

Marathon house

7 bedrooms / 9 bathrooms / sleeps 14

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,491

Kokomo Cove Boat House

Marathon house

2 bedrooms / 2 bathrooms / sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

Match: Private outdoor pool (heated)

All filters match

Price per night from

$200

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$617

100' Private Beach Front Ocean Front Estate

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 21 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,088

Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Fabulous luxury home in Fabulous Key West” Beautiful, private, historic 2 BR/2 bath home, lovely heated pool, outdoor dining & living areas in addition to most attractive indoor spaces. Wonderful Old Town neighborhood. Can walk, cycle, & Lyft everywhere (including great restaurants)--no car needed. 2nd BR is in the guest house beyond the pool--fabulous outdoor shower completes the "only-in-Key West" ambiance. The owner, Kim, is super responsive.

Responds fast! avg. 1 hour 50 minutes

Travelers’ Choice award

Match: Private outdoor pool (heated)

All filters match

Price per night from

$605

CONCH BAR SOUTH

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$317

Viewing 38 of 225
rentals in Florida Keys

×

Also consider