Vacation Rentals & House Rentals in Florida Keys

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117 house rentals

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Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$391

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$573

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

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$917

Coastal Waterway

Key Largo caravan/mobile home

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$130

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$2,211

Oceanfront Anglers Reef Islamorada Florida Keys

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$458

Waterfront Key Largo Bayside Cottage Paradise

Key Largo cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Hidden Treasure” This cottage is one of our favorite place to stay. Clean, well equipped, private, and so relaxing. A great place to spend a relaxing vacation. We love the outdoor kitchen and sitting area.

Responds fast! avg. 56 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$253

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$159

Welcome to Paradise

Long Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$206

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 2 hours 56 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$327

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$402

Responds fast! avg. 2 hours 44 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$247

Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$573

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!

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$343

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$2,407

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$622

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$562

“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. 1 hour 0 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$671

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$500

Florida Keys Beach Home Pool Fishing Diving

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$2,293

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$402

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

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$1,147

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$336

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$230

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$201

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$1,490

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$1,147

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$2,129

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$1,948

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$458

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$983

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$802

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$1,031

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$803

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$333

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$1,147

Paridise Found

Tavernier house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$764

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private fishing lake or river, Sea view

1 of 2 filters match

Price per night from

$287

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