Vacation Rentals & House Rentals in Florida Keys

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364 house rentals

Amazing Ocean View Condo on the Beach!

Marathon apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$343

Key Largo Mariners Club Paradise: Largest Unit, Abundant Amenities!

Key Largo townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$687

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$915

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 2 hours 7 minutes

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$343

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Price per night from

$487

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$229

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$654

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

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Price per night from

$659

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$264

BREATHTAKING Ocean views await at Tropical Daze

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 2 hours 17 minutes

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$286

Best Kept Secret,Port Largo Villas In Key Largo,FL

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$224

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$258

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$434

Reef Resort Getaway 205

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$320

LICENSED MGR. - 2 KING BEDS! - OCEANFRONT LUXURY/BEACH! - TOTALLY REMODELD UNIT!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

“great place with a view .” Wow! What a great relaxing time we had! The 2/2 condo was great, very clean and comfortable. Has everything needed to a week long or longer stay.The view from the balcony was great overlooking the marina to the south and sunsets to the west. . The location was very private and had a very laid back atmosphere. Everyone we met there was very friendly. Dining in the area is also great place. We can't wait to come down here and and do this again. We might even bring our kids.

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$212

Bayside Condo, marina, pool and beach

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I've had the pleasure of staying at this condo several times and have honestly never had a bad time (even during a cat 5 Trop Storm). There is too much to do, the condo is comfy, and the weather is always beautiful. Definitely recommend this condo!

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$253

Luxury Vacation Rental Oceanfront in Key Largo, nr, Islamorada, Florida Keys

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Great place to stay” We stayed at Sally and andrew´s place for a week. When we looked for a place to stay, we wanted a place not to far of Key West and Miami, and this place was just great! There were lots of places to eat out, things to see, and Key West and Miami was not to far away. The apartment was great, Andrew was too! Everthing regarding the stay were done in a professionel way. Both before the stay and after. The way of paying could have been easier though, but that is not a big problem We had a great time, all four of us visiting from Norway. If anyone should ask me where to stay in that erea, I have absolutely no problem telling them about Sally and andrew´s place! Ps: Make shure to have the time to eat at Mrs Mac´s Kitchen...

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$207

Reef Resort - Peaceful Getaway 204

Marathon condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$352

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$355

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$916

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$391

Experience the Florida Keys like never before!!!

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$245

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$1,946

LICENSED MGR. - LUXURIOUS OCEANFRONT CONDO! - W/STUNNING OCEAN/ISLAND VIEWS!

Key Largo hotel apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$401

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$158

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$252

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$81

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$1,144

“The most relax g vacation..Awesome” We stayed at Mariners Run Key Largo.the place was beautiful,clean, state of the art appliances.there was nothing Fernanado didn't think us. my entire family raved about the rental.the pool was beautiful .we had two adjoining townhouses so it work put perfect ,more than enough room.

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$401

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$344

LICENSED MANAGER - MODERN 2/2 VILLA - OCEANFRONT BEACH RESORT & MARINA!

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Nationals” Beautiful home with separate pool house. Imaculately decorated, awesome pool area, great location and wonderful owners. You can't go wrong with this unit!

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$201

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$457

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 2 hours 41 minutes

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$343

OCEAN VIEWS ALL ROOMS ! TOP FLOOR LARGEST CONDO

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$373

Henry's Piece Of Paradise On The Ocean In Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“nice place” Accommodations were nice Good view Henry was great to work with

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$464

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$457

Outstanding Oceanfront Condo on the Beach!!

Marathon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$343

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Shared outdoor pool (heated) Towels provided

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Price per night from

$1,144

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