Search 105,200+ Vacation Rentals

Florida Keys Vacation Rentals & House Rentals with Swimming Pool - 84 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

84 Vacation rentals

Filters applied: Swimming pool

(119)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“we can"t say enough about the condo or Pam. She takes good care of her rental. Always clean and comfortable.The balcony overlooks the pool area which is well maintained. Pam is always available to answer any questions you might have. We stay the...”
- Review left on 12/03/2016

$200

Excellent (119 reviews)

Book

from $200 / night

(1)

1 / 23

Marathon Shores House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$425

Excellent (1 reviews)

Book

from $425 / night

(5)

1 / 15

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We stayed for a week and had a wonderful holiday. The booking and communication with the owner was good and the accommodation is exactly as described. It is a lovely clean well equipped apartment in a central location. Easy walk to all of the...”
- Review left on 07/13/2016

$228

Excellent (5 reviews)

Inquire

from $228 / night

(3)

1 / 33

Islamorada House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoy coming back, weather just great. Just so relaxing. Chiki bar, pool, private dock all a plus. Est place to vacation...”
- Review left on 10/17/2016

$457

Excellent (3 reviews)

Inquire

from $457 / night

(5)

1 / 14

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We (2 retired couples) enjoyed our stay at Rooster Retreat. What you see in the pictures is true to what you get, but I will add that the "twins to king conversion" is probably the best I have ever experienced. It just did not "feel" like twins --...”
- Review left on 03/12/2017

$186

Very Good (5 reviews)

Inquire

from $186 / night

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$275

Very Good (7 reviews)

Book

from $275 / night

(3)

1 / 6

Key West Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$295

Very Good (3 reviews)

Book

from $295 / night

1 / 25

Marathon House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $300 / night

(11)

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house and lush landscaping are beautiful! We enjoyed the pool so much. The private dock is a great touch even though we don't have a boat. We would recommend this property highly! Quaint restaurants in Marathon have some great food, too! We...”
- Review left on 11/03/2014

$394

Excellent (11 reviews)

Inquire

from $394 / night

(7)

1 / 9

Islamorada House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“We had four couples on our summer fishing vacation that we do every year in Islamorada.Couldnt have been better,we had couple days at first to go feed tarpon at Robbies and relax till seas calmed down and we got out in flat waters to fish,we caught...”
- Review left on 05/29/2015

$429

Excellent (7 reviews)

Book

from $429 / night

1 / 16

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1000

Inquire

from $1000 / night

(48)

1 / 34

Cudjoe Key House

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$414

Very Good (48 reviews)

Inquire

from $414 / night

(19)

1 / 20

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house was just as pictured. Swimming in the gulf and canoeing was great. Waking up to that beautiful view every morning was wonderful. It's centrally located and close to everything. Definitely would stay again...”
- Review left on 01/03/2017

$343

Excellent (19 reviews)

Inquire

from $343 / night

(2)

1 / 16

Tavernier Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My family and I had a fabulous time. Enjoyed all the perks available. Close to a local shopping center which has everything you may need. We will be back...”
- Review left on 12/02/2016

$175

Excellent (2 reviews)

Book

from $175 / night

(50)

1 / 36

Key West Condo

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed our stay at the Sunrise Suite. The place was bright with sunshine. It was clean, comfortable, nice sitting balcony and close to Duval Street. It had everything you would need for your stay. You could walk thru the complex and cross the...”
- Review left on 03/06/2017

$209

Excellent (50 reviews)

Inquire

from $209 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
“This unit was great! The location is fantastic! The condo is spacious, clean and everything we were hoping for. I like that the bedrooms are upstairs which offers more privacy...”
- Review left on 01/12/2017

$200

Excellent (17 reviews)

Inquire

from $200 / night

(8)

1 / 8

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“It could not have been better. The owners were excellent, and the home had everything imaginable. We will be back...”
- Review left on 12/25/2016

$243

Excellent (8 reviews)

Inquire

from $243 / night

1 / 23

Marathon Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$245

Book

from $245 / night

(17)

1 / 42

Key Largo Cottage

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
“Our family of 4 stayed here over Thanksgiving week and had the best time. Penny is very organized and everything was perfect, love the ambiance. We love the old Florida feel and the tiki hut is the best. Our teenage boys had a fantastic time swimming...”
- Review left on 04/14/2016

$100

Excellent (17 reviews)

Inquire

from $100 / night

(1)

1 / 23

Key West House

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house is immaculately kept and one of the few houses on a canal in KW. Beautiful interior and plenty of room in the bedrooms. The pool overlooks the canal and has an absolutely beautiful view! If you want a house that makes you feel like you're...”
- Review left on 03/10/2015

$133

Excellent (1 reviews)

Inquire

from $133 / night

1 / 30

Marathon House

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $427 / night

1 / 24

Duck Key Villa

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $340 / night

(1)

1 / 20

Key Colony Beach Condo

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Great location on the water. Pleasant heated large pool. Small number of units and lots of room on the grounds. Pier and beach. Clean, quiet, and well kept inside and out by owners there. Got an invite to meet for a birthday party and got to...”
- Review left on 02/06/2016

$103

Excellent (1 reviews)

Inquire

from $103 / night

(11)

1 / 60

Key Largo Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We loved your place. It is so nicely decorated, furnished with everything we could have needed and so very clean! I loved being able to walk to the water and fish from the pier. It was hard to decide whether to go in the pool, ocean or ping pong...”
- Review left on 02/08/2017

$128

Excellent (11 reviews)

Inquire

from $128 / night

(10)

1 / 17

Marathon House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Following our wedding in the Caribbean we booked this house as part of our honeymoon sharing the house with our teenage sons and another couple. The house and location was perfect for us, our only regret that we didn't have longer. The house itself...”
- Review left on 08/01/2016

$314

Very Good (10 reviews)

Inquire

from $314 / night

(3)

1 / 31

Marathon House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Stayed with my family of 5. Plenty of room, great spot. Would recommend. Check pics, they are true to the rental...”
- Review left on 03/18/2017

$427

Very Good (3 reviews)

Inquire

from $427 / night

(1)

1 / 15

Key Largo Condo

  • 2
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We really enjoyed our stay at your beautiful property. The condo had everything we needed, from comfortable beds to a well-equipped kitchen. We especially enjoyed the view, fishing off the dock, barbequing and being able to walk to many great...”
- Review left on 12/11/2016

$145

Excellent (1 reviews)

Inquire

from $145 / night

(12)

1 / 24

Islamorada House

  • 5
  • 15
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This is the second time we've rented this house and it was better than the first time. Beautiful views and easy access to the bay was exactly what we were looking for. The new ice maker and huge refrigerator were perfect for our large group. Amazing...”
- Review left on 07/11/2016

$643

Very Good (12 reviews)

Inquire

from $643 / night

(3)

1 / 15

Tavernier House

  • 5
  • 10
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We have just returned from a month long celebration of retirement in the Keys. The lovely home we stayed in was perfectly located smack dab in the middle of everything there is to do in the Keys! The owner of this property was quick to respond to...”
- Review left on 02/05/2016

$167

Excellent (3 reviews)

Inquire

from $167 / night

(3)

1 / 20

Summerland Key House

  • 4
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house was great. Had everything you could ask for. The owner even called to make sure we made it ok and if we needed anything. Best view, plenty of space absolutely gorgeous couldn't of asked for better...”
- Review left on 08/19/2014

$233

Excellent (3 reviews)

Inquire

from $233 / night

(1)

1 / 13

Marathon House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“What a perfect home. You can tell the owners have taken great care to see that the vacationers have everything they need. In my 7 years of staying in Marathon, this is the first home that had absolutely everything I could need. (I have stayed at...”
- Review left on 08/03/2015

$427

Excellent (1 reviews)

Inquire

from $427 / night

1 / 24

Duck Key Villa

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $535 / night

(3)

1 / 28

Key West Villa

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This house is great for large groups. We had such a fun time having a reunion here. Close to everything, and staff was attentive and friendly...”
- Review left on 09/08/2016

$1195

Excellent (3 reviews)

Book

from $1195 / night

(16)

1 / 21

Key West House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We rented Casa Rosa with three other couples for a week in February, 2017. Location was terrific! We could walk to many restaurants,bars, beaches and one grocery store (Fausto's). Suitable size for 8 people. Liked that each couple had their own...”
- Review left on 03/05/2017

$541

Very Good (16 reviews)

Inquire

from $541 / night

(3)

1 / 55

Key West Villa

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“I rented this house for my sister-in-law's bachelorette weekend. The house was spacious, clean, and overall one of the best houses we've stayed in...”
- Review left on 09/27/2016

$829

Excellent (3 reviews)

Inquire

from $829 / night

(12)

1 / 16

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“When we found this rental online, we knew it was what we were looking for. Very private, quiet and peaceful. As other reviewers have said, really nice house, but could be amazing. Many items in rental are dated, a few found not to work properly. We...”
- Review left on 03/13/2017

$315

Very Good (12 reviews)

Inquire

from $315 / night

(3)

1 / 37

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This home was more than expected. It was close enough to all the night life of Duval Street, yet are enough to enjoy peace and quiet when needed. I would recommend this home to anyone looking for a great vacation getaway...”
- Review left on 05/20/2015

$356

Very Good (3 reviews)

Inquire

from $356 / night

(3)

1 / 17

Key Largo Townhouse

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Norm was thorough in the walk through of the property we stayed. Townhouse condo was clean and well stocked. Next to salt water lagoon and pool. All the water toys were made available like snorkels, fins, fishing rods, kayaks and paddleboards. Golf...”
- Review left on 03/25/2017

$200

Average (3 reviews)

Inquire

from $200 / night

(25)

1 / 16

Key Largo Villa

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This place was awesome-everything included we had paddle boards, Kayaks, golf cart and bicycles. The host Norman couldn't have been more friendly and helpful. I recommend this getaway to anyone and it is pet friendly...”
- Review left on 01/19/2017

$300

Very Good (25 reviews)

Inquire

from $300 / night

(18)

1 / 26

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

$372

Excellent (18 reviews)

Book

from $372 / night