Vacation Rentals & House Rentals in Florida Keys

Updating...

age 0-16
265 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

265 house rentals

SPECIAL FALL RATES, INCL. LABOR DAY - BOOK NOW!

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 53 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$287

Duck Key Paradise

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 12 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$287

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 13 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$258

Keys Cove Home #4 Wave from it all

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 41 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$572

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

Islamorada apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 55 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$201

Family Retreat ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 18

Match: Private outdoor pool (heated)

All filters match

Price per night from

$573

The Water's Edge

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do during your Key West experience. Ocean Paradise has gorgeous views from the 3rd level balcony, a wonderful screened-in porch on the main level (perfect for al fresco dining), and an incredible pool area with a larger than expected private pool and stunning landscaping that provides both shade and privacy. The home's interior is both spacious and functional, including lovely furnishings and everything you need for a memorable vacation in beautiful Key West. Just as important to us was the ease in managing our visit to Ocean Paradise. The owner and his staff were absolutely incredible to work with throughout the entire rental process. We had originally scheduled our visit for the 2014 Thanksgiving holiday week. However, a need arose which required us to cancel that planned stay. The property owner was gracious enough to work with us in our desire to reschedule our visit for May 2015, demonstrating a focus on and respect for his guests throughout the entire process. Our Key West vacation, and specifically our week-long stay in Ocean Paradise, was undoubtedly a memorable experience for me, my husband and our two adult children (as well as the little "furry" member of our family who also joined us for our Key West adventure). We will be returning to Key West, and when we do, Ocean Paradise will be our chosen "home away from home" during our stay!

Match: Private outdoor pool (heated)

All filters match

Price per night from

$846

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. 3 hours 13 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$654

KEY LARGO YACHT CLUB 8

Key Largo apartment

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$140

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

$345

Hidden Treasure

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (heated)

All filters match

Price per night from

$127

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!!

Responds fast! avg. 3 hours 17 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$246

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

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 19 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$339

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 34 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$460

Million $$ Pool Home

Key Colony Beach house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$441

New Rental Sombero Beach

Marathon Shores house

4 bedrooms / 5 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$857

Island Style

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$698

Blue weekly vacation rental, great view. Heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$394

Canal-Side 4BR 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

$344

Admiral's Lane

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“Fabulous family rental” We have stayed in Key West for four years now. This was the best rental property so far. The location is perfect for beach days and walking both ends of Duval at night. The property itself had all the amenities we needed and was run well by the property managers. The major reason we didn’t give five stars is that all of the tv’s were from the 90’s. They offered cable but on screens that are archaic. Not great for unwinding or catching up with March Madness. For this level of home/rental, the owners could spring for even just ONE flat screen.

Match: Private outdoor pool (heated)

All filters match

Price per night from

$602

The Mermaid's Garden

Key West house

4 bedrooms / 5 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$625

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Match: Private outdoor pool (heated)

All filters match

Price per night from

$571

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

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 34 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$173

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

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$262

Villa Deja vu Key West ~ Weekly Rental

Key West house

4 bedrooms / 3 bathrooms / sleeps 10

“Great stay over the 4th of July” The Villa Deja Vu was the perfect place for our group of 10. We were on vacation in Key West for a 30th birthday celebration and had a great experience. The house was wonderful, more than we could have imagined. The pictures online truly do not give it justice. It is beautiful and brightly colored. The house was stocked, clean and comfortable for a large group. The grounds were in pristine condition and the location of the home was perfect for any activity on the island. We walked everywhere! Having a pool right in the backyard was such a great amenity. We used it every day. Most of the day we were even able to get a suntan there, even though it is hidden and private. We had one issue during our second day, the propane was empty for the grill. I called maintenance and they showed up within 15 minutes. The service was better than I could've asked for. My only suggestion for the property would be to add lighting out back for evenings at the house. We tended to eat dinner late, and used our phones for light over the grill.

Match: Private outdoor pool (heated)

All filters match

Price per night from

$878

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“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 19 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,805

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

$195

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 1 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,260

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. 28 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$608

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

$705

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!

Match: Private outdoor pool (heated)

All filters match

Price per night from

$400

Gated Canal-Front 4BR w/ Hot Tub, Heated Pool, Gourmet Kitchen & Boatslip

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$366

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

$215

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$108

Grande Dame Key West - 'The Watson House' ~ Weekly Rental

Key West house

7 bedrooms / 7 bathrooms / sleeps 14

“One of the best vacations I've taken.” There were a total of 16 people staying in the main house and the cottage. We were there celebrating a friends 50th birthday. The houses were wonderful!! They were clean andthe amenities were great!! The kitchens saved us from having to go out every morning to eat. We put the food in the main house kitchen and had our beer and liquor in the cottage refrigerator. :) The 3 washers and dryers came in handy also. You don't have to bring as many outfits and save on the baggage fees. Loved the pool and the hot tub. Every night after coming home from our adventures, we would all take a dip in the pool or soak our aching bodies. Lol The location is wonderful!! It is one block from Duval Street and only blocks from other attractions, stores and the waterfront. We were there for 8 days and 7 nights and the value was great. You could not get a hotel room for the price it came out per person. While we were there we all talked about definately coming back and renting this property. Also, if you are looking to just come as a couple the cottage is a great place to rent alone. You still have use of the pool and the hot tub. If you do rent the house please remember to think of your neighbors after 11 at night. :)

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,655

Oksana's Tropical Beach Oasis

Cudjoe Key house

4 bedrooms / 3 bathrooms / sleeps 14

Match: Private outdoor pool (heated)

All filters match

Price per night from

$502

Sunshine Key West

Key West house

2 bedrooms / 3 bathrooms / sleeps 5

“Perfect Home for Key West” This place has all the amenities you need! It was our first time renting a home and it couldn't have been more perfect! Quiet neighborhood, but not too far from the action of Duval.

Match: Private outdoor pool (heated)

All filters match

Price per night from

$108

Viewing 38 of 265
rentals in Florida Keys

×

Also consider