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Florida Keys Waterfront Vacation Rentals, House Rentals & More - 178 Rentals Available.

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178 Vacation rentals

Filters applied: Waterfront

1 / 19

Marathon Shores Townhouse

  • 3
  • 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$325.00

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from $325.00 / night

1 / 11

Key Largo Cottage

  • 1
  • 4
  • 3 nights min
  • Child friendly
  • Air conditioning

$167.00

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from $167.00 / night

(15)

Certificate of Excellence

1 / 19

Conch Key Cottage

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly

Certificate of Excellence

$175.00

Excellent (15 reviews)

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from $175.00 / night

(3)

1 / 16

Key Largo Apartment

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We were in the Tower unit 212 at the Kawama Yacht Club. Norman Wartman met us and gave a tour of the facilities. Norman was very helpful and kept us in stitches with his barrage of jokes. The condo was in very good condition and the kitchen was...”
- Review left on 11/29/2016

$250.00

Excellent (3 reviews)

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from $250.00 / night

(2)

1 / 17

Tavernier Condo

  • 2
  • 6
  • 1 night min
  • 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

$235.00

Excellent (2 reviews)

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from $235.00 / night

1 / 12

Key West House

  • 2
  • 4
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$465.00

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from $465.00 / night

(48)

1 / 12

Key Largo Cottage

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We enjoyed our Key Kargo stay. Our daughter and son in law joined us. Everything on site made for a good vacation. We were lucky to have good weather for snorkeling on the reef. Only request would be to have more plates and cutlery. We like to...”
- Review left on 01/07/2018

$175.00

Very Good (48 reviews)

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from $175.00 / night

(22)

1 / 15

Key Largo House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We stayed for five days. Two families with five small children. The house was perfect! There are toddler beds tucked into 2 large walk in closets. There were two cribs and a high chair. They even had baby spoons! There is an adorable pirate ship...”
- Review left on 03/03/2016

$350.00

Very Good (22 reviews)

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from $350.00 / night

(19)

Certificate of Excellence

1 / 24

Conch Key Cottage

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly

Certificate of Excellence

$150.00

Excellent (19 reviews)

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from $150.00 / 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

$325.00

Excellent (5 reviews)

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from $325.00 / night

(139)

1 / 28

Key West Apartment

  • 2
  • 5
  • 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

$215.00

Excellent (139 reviews)

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from $215.00 / night

(2)

1 / 17

Key Largo Townhouse

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“The location is amazing everything is so close, shopping, nightlife! This our second year coming back every one is so friendly. We loved it. You don't need to go nowhere Norman the owner has everything that you need , kayak,snorkeling gear fishing...”
- Review left on 03/23/2017

$250.00

Excellent (2 reviews)

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from $250.00 / night

(7)

1 / 22

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

$322.00

Excellent (7 reviews)

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from $322.00 / night

(12)

1 / 17

Marathon House

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$436.00

Excellent (12 reviews)

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from $436.00 / night

1 / 26

Key Largo Cottage

  • 1
  • 4
  • Min stay varies
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning

$175.00

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from $175.00 / night

1 / 20

Marathon Shores Townhouse

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

$476.00

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from $476.00 / night

(11)

1 / 24

Key Largo House

  • 3
  • 9
  • 28 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My family and my sister's family visited this wonderful home over Spring Break and couldn't have been happier. Helen did everything she could to make sure we were comfortable and quickly settled so that we could get straight down to enjoying...”
- Review left on 07/19/2017

$200.00

Excellent (11 reviews)

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from $200.00 / night

1 / 24

Marathon Condo

  • 2
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$242.00

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from $242.00 / night

1 / 24

Marathon Villa

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$200.00

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from $200.00 / night

1 / 25

Marathon House

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

$350.00

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from $350.00 / night

1 / 19

Key West Yacht

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$200.00

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from $200.00 / night

(19)

1 / 27

Islamorada House

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This house is the best!!!!! We had two familys staying and was perfect. The separate living quarters made our trip very enjoyable and very roomy. The house upstairs is remarkable and very up to date as well as downstairs. The back yard is your own...”
- Review left on 08/09/2016

$458.00

Excellent (19 reviews)

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from $458.00 / night

(13)

1 / 16

Key Largo Villa

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The Condo was very spacious, clean and very well presented. With a family, we appreciated the room and comfy beds! The washer and dryer were an added bonus. We liked the location and really enjoyed our stay. We wish it was longer and would love...”
- Review left on 12/06/2016

$200.00

Excellent (13 reviews)

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from $200.00 / night

(1)

1 / 35

Key Largo Cottage

  • 1
  • 3
  • Min stay varies
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning

$175.00

Excellent (1 reviews)

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from $175.00 / night

1 / 23

Marathon Townhouse

  • 3
  • 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$245.00

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from $245.00 / night

1 / 10

Key Largo Cottage

  • 1
  • 4
  • 1 night min
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning

$200.00

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from $200.00 / night

1 / 10

Marathon Cottage

  • 1
  • 4
  • 3 nights min
  • Child friendly
  • Air conditioning

$167.00

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from $167.00 / night

(2)

1 / 29

Cudjoe Key House

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
“The view was outstanding, the property had great amenities, and the home had all items as advertised. We were happy campers...”
- Review left on 03/13/2017

$175.00

Very Good (2 reviews)

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from $175.00 / night

1 / 17

Summerland Key House

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$142.00

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from $142.00 / night

(27)

1 / 16

Key Largo Villa

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“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

$400.00

Very Good (27 reviews)

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from $400.00 / night

(9)

1 / 15

Marathon Shores House

  • 4
  • 8
  • 7 nights min
  • Nearest beach 10 mi
  • Child friendly
  • Air conditioning
“Great place to stay, owner easy to reach and help if needed. Great dock for your boat, easy to park tie up and launch. House very clean and felt like home, I plan to stay there again”
- Review left on 01/06/2016

$300.00

Very Good (9 reviews)

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from $300.00 / night

(62)

Certificate of Excellence

1 / 25

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

“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

$210.00

Excellent (62 reviews)

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from $210.00 / night

(1)

1 / 16

Marathon House

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“My family and I went and stayed at this house for a week and had the most amazing time. The house was buitiful and very clean. The place had everything for the kids as well and for me to. I can't thank them enough for letting us stay in their...”
- Review left on 10/02/2016

$429.00

Excellent (1 reviews)

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from $429.00 / night

1 / 29

Key Largo Cottage

  • 1
  • 5
  • Min stay varies
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning

$185.00

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from $185.00 / night

(23)

1 / 32

Key Largo Condo

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We have been coming to Key Largo for the past three years and by far this was our most enjoyable stay. We are looking forward to returning next year. You could not asked for a better host than Norman. Very accommodating. The location is excellent...”
- Review left on 05/15/2017

$250.00

Very Good (23 reviews)

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from $250.00 / night

(36)

1 / 19

Marathon Villa

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Peninsular House ? Marathon, Florida We had a great time celebrating our 25th Wedding Anniversary at the Peninsular House ? gives you the feel of what ?old Florida? would be like - away from everyone, but actually just a hop, skip and jump from...”
- Review left on 05/25/2017

$358.00

Very Good (36 reviews)

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from $358.00 / 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

$286.00

Excellent (8 reviews)

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from $286.00 / night

(20)

1 / 22

Key West B and B

  • 4
  • 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$800.00

Excellent (20 reviews)

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from $800.00 / night

(28)

1 / 36

Marathon House

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“We were looking for a place to get away from the fast pace world. This place was a perfect fit. While the villas could use some updates, we spent most of time at the pool or the private beach. We visit the Keys every year for a quick weekend...”
- Review left on 07/02/2016

$150.00

Very Good (28 reviews)

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from $150.00 / 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

$207.00

Very Good (5 reviews)

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from $207.00 / night