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262 Vacation rentals

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$295

Very Good (7 reviews)

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from $295 / night

1 / 24

Marathon Villa

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

from $200 / night

(9)

1 / 21

Key West Condo

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
“We stayed at Touch of paradise at teh end of Oct and into Nov. Perfert location. I have stayed in Truman Annex many times and Touch of Paradise was a wounderful Unit. Location is everything in Kw because you walk alot and this unit is close to...”
- Review left on 11/13/2016

$228

Excellent (9 reviews)

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from $228 / night

(8)

1 / 56

Key Largo House

  • 3
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My family of five stayed in this home. We cooked on the grill while relaxing by the water watching the manatees. Plenty of space. Owners were super sweet and easy to work with during the stay”
- Review left on 01/10/2017

$229

Excellent (8 reviews)

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from $229 / night

(44)

1 / 12

Key Largo Cottage

  • 2
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“we were very pleased with our stay at Alamar. We actually were the only ones on the property that weekend. It was quiet and very tranquil. I recommend this hidden little gem. We brought our two dogs and on Saturday rode down to the Islandmorada Fish...”
- Review left on 10/12/2016

$200

Very Good (44 reviews)

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from $200 / night

1 / 9

Long Key House

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $357 / night

(118)

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 (118 reviews)

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from $200 / night

(11)

1 / 51

Marathon House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“We have been Lucky enough to get Married at Seabird Key in 2005 & have been going back for our Anniversary ever since. It is truly amazing place away from everything . It is very well kept outside & Inside .very clean. It is beautiful & worth every...”
- Review left on 03/18/2016

$900

Excellent (11 reviews)

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from $900 / 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)

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from $457 / night

1 / 20

Matecumbe Key Townhouse

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $100 / night

1 / 37

Marathon Villa

  • 3
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

from $214 / night

(12)

1 / 18

Marathon House

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“It was a great place to stay. Very nice and clean. Location is great. Neighbors are friendly. For the fisherman, this place is great. Caught several fish. Would definitely refer this place to others. Look forward to coming back...”
- Review left on 11/03/2016

$257

Very Good (12 reviews)

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from $257 / night

(4)

1 / 3

Summerland Key Guest house

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We rented the Conch House for our honeymoon and it was perfect! We loved the secluded feeling and the private beach. Carol was wonderful to work with and had fresh eggs and champagne waiting for us in our fridge. She picked fresh veggies for us to...”
- Review left on 04/20/2016

$393

Excellent (4 reviews)

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from $393 / night

(2)

1 / 23

Cudjoe Key House

  • 2
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“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

$157

Very Good (2 reviews)

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from $157 / night

(3)

1 / 6

Key West Apartment

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

$295

Very Good (3 reviews)

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from $295 / 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)

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from $209 / night

1 / 25

Marathon House

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

from $300 / night

1 / 23

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $177 / 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)

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from $186 / night

(4)

1 / 9

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The canal front cottage was beautiful . Super clean perfectly furnished, hey 3 flat screens First class cooking utensils. Grill chairs by the dock, water, fish station & great light for night activity. Owner and manager readily available, most...”
- Review left on 08/30/2015

$156

Excellent (4 reviews)

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from $156 / 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

$393

Excellent (11 reviews)

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from $393 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
“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

$257

Excellent (17 reviews)

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from $257 / night

(9)

1 / 16

Conch Key Cottage

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$185

Excellent (9 reviews)

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from $185 / 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)

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from $167 / night

1 / 24

Duck Key Villa

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

from $340 / night

(17)

1 / 24

Key Largo House

  • 4
  • 15
  • 30 nights min
  • Ask about children
  • Air conditioning
“My wife and I rented this home for our 30th anniversary along with my two daughters and our son in law and had a awesome time. We will rent this home again next year. It was a pleasure dealing with Dave...”
- Review left on 11/02/2016

$333

Very Good (17 reviews)

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from $333 / night

(7)

1 / 22

Key Largo House

  • 3
  • 9
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“By far the best spot in the Keys. Amazing views, breathtaking sunsets, and most importantly a place that feels like home. We love it so much 2016 will be our forth year. The home is imaculate from the wonderful bedding to the very well stocked...”
- Review left on 05/30/2016

$350

Very Good (7 reviews)

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from $350 / night

1 / 23

Key Largo House

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $321 / night

(2)

1 / 17

Key Largo Townhouse

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

Excellent (2 reviews)

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from $250 / night

(10)

1 / 28

Marathon House

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“# families, 8 kids ranging from 2-14yrs stayed here for a week. Absolutely could not be happier! Pool was fantastic and warm, hot tub was well maintained, and clean. Grounds were breathtakingly beautiful. Kyaks were readily available, and easy to get...”
- Review left on 01/19/2017

$414

Very Good (10 reviews)

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from $414 / night

(3)

1 / 16

Marathon Condo

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
“Had a fantastic time at the Gulfpointe condo in Marathon, FL. The location was great, the condo was spacious and had all the items needed to make our trip memorable for our family of three. The pool is great - spent a lot of time there. Beaches in...”
- Review left on 04/09/2015

$177

Very Good (3 reviews)

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from $177 / night

1 / 23

Marathon Townhouse

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

$245

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from $245 / night

(9)

1 / 4

Key West Townhouse

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Traveling Buddies (3) rented this beautiful, recently renovated single-family townhouse in February, 2012 for two weeks. The house is so perfect in everyway-fully equipped...close to Duval St yet behind the gate and setback from busy Truman, its...”
- Review left on 03/27/2012

$100

Excellent (9 reviews)

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from $100 / night

(1)

1 / 43

Marathon House

  • 4
  • 10
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
“This place is absolutely AMAZING! We stayed here with 3 families and we had plenty of room. Everything from the beautifully maintained grounds to the spacious house made this stay amazing! The views of the sunsets from the balcony were outstanding....”
- Review left on 10/01/2016

$300

Excellent (1 reviews)

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from $300 / night

(1)

1 / 20

Tavernier Apartment

  • 3
  • 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Futura Yacht Club was great- our condo was 2 bedroom. The condo is older but I was pleased with how clean it was, The pool area was very new and renovated- club area - nice! People were friendly- we enjoyed dinner at picnic tables ocean side-...”
- Review left on 04/09/2015

$161

Excellent (1 reviews)

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from $161 / 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)

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from $100 / 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)

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from $103 / night

(1)

1 / 24

Marathon House

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$257

Excellent (1 reviews)

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from $257 / 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)

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from $243 / night

(38)

1 / 10

Marathon House

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We were very pleasantly surprised at the location of this rental. We loved the view of the sunrises over the water. The home was very adequately supplied with all kitchen utensils. Grill outside had plenty of gas. They had fresh flowers to please...”
- Review left on 02/25/2017

$157

Very Good (38 reviews)

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from $157 / night