Cottages Florida Keys

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124 cottages

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

Match: Rental types Sea view

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Price per night from

$251

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

Match: Rental types Sea view

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Price per night from

$326

Match: Rental types Sea view

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Price per night from

$559

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Rental types Sea view

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Price per night from

$456

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Coastal Waterway

Key Largo caravan/mobile home

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Sea view

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Price per night from

$129

Paridise Found

Tavernier house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 13

1 of 2 match: Rental types, Sea view

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Price per night from

$760

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Sea view

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Price per night from

$2,201

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Sea view

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Price per night from

$183

Breezy Palms

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Sea view

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Price per night from

$656

Cabanas Key Largo Unit 6

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Pleasant place to stay for a few days” We got off on a bad foot as the room had not been cleaned before our arrival at 4:30PM (we were told we could check in a 3PM). The management was very responsive however, and paid for a complementary dinner at a fun, nearby restaurant by way of apology. The room was well designed and comfortable, if not spacious; the kitchenette and living/bedroom are all in one layout. It was fine for 2 guests but there would be no privacy if there were more. The cabana is right on the canals; boats pass frequently but it's not noisy. This was our first visit to the Florida Keys, and this cabana was a comfortable base for seeing Key Largo. It's not as convenient if you want to go as far south as Key West.

Responds fast! avg. 2 hours 15 minutes

1 of 2 match: Rental types, Sea view

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Price per night from

$172

Key Largo Oceanfront Condo with Dock and Spectacular views

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Rental types, Sea view

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Price per night from

$400

Paradise on the water

Key Largo house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Sea view

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Price per night from

$571

Shipyard-1/2 Block Duval Street

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Rental types, Sea view

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Price per night from

$229

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Sea view

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Price per night from

$326

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Rental types, Sea view

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Price per night from

$382

Beachfront Islamorada Villa with Dockage and Bay Views

Lower Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Sea view

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Price per night from

$347

Beautifully Designed Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Sea view

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Price per night from

$462

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Sea view

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Price per night from

$970

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Rental types, Sea view

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Price per night from

$200

Oceanfront Condo w/Lake, Kayaks, Paddleboards & Bikes

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Sea view

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Price per night from

$445

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Sea view

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Price per night from

$250

Blue Moon Tavernier

Tavernier house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Rental types, Sea view

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Price per night from

$400

1 of 2 match: Rental types, Sea view

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Price per night from

$599

Gorgeous Vacation Home with Beach Access!

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Rental types, Sea view

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Price per night from

$599

Vacation in Tropical Paradise with the Family! Waterfront Townhome in Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Rental types, Sea view

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Price per night from

$599

Waterfront Vacation Home in The Florida Keys!

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Sea view

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Price per night from

$456

Islamorada Waterfront Townhome w Priv. Beach! Comfortable Family Vacation Rental

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Sea view

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Price per night from

$599

Outstanding Oceanfront Condo on the Beach!!

Marathon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Sea view

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Price per night from

$341

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: Rental types, Sea view

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Price per night from

$571

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: Rental types, Sea view

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Price per night from

$341

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Rental types, Sea view

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Price per night from

$619

“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: Rental types, Sea view

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Price per night from

$668

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Rental types, Sea view

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Price per night from

$498

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Rental types, Sea view

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Price per night from

$400

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

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Rental types, Sea view

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Price per night from

$913

Welcome to Paradise

Long Key townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

1 of 2 match: Rental types, Sea view

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Price per night from

$205

2 BEDROOM 2 1/2 BATH VILLA WITH PRIVATE PATIO AND PLUNGE POOL

Duck Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 13 minutes

1 of 2 match: Rental types, Sea view

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Price per night from

$337

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Rental types, Sea view

1 of 2 filters match

Price per night from

$1,939

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