Vacation Rentals & House Rentals in Florida Keys

Updating...

age 0-16
210 Results

Relevance

Price: low to high

Price: high to low

Reviews

210 house rentals

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

Match: Boat available Pets allowed

All filters match

Price per night from

$286

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Boat available Pets allowed

All filters match

Price per night from

$685

“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.

Match: Boat available Pets allowed

All filters match

Price per night from

$2,396

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

Match: Boat available Pets allowed

All filters match

Price per night from

$407

Key Largo Rental Fantastic Views

Key Largo condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

Match: Boat available Pets allowed

All filters match

Price per night from

$400

the private and secluded PENINSULARHOUSE

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Nice get away” Beautiful and relaxing. Did alot of snorkeling right off the deck. Enjoyed the paddle boats and the kayaks. When we make it down that way again I would definitely stay here.

Match: Boat available Pets allowed

All filters match

Price per night from

$400

Diving, Fishing, Snorkeling, Kayaking Paradise

Key Largo townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

Match: Boat available Pets allowed

All filters match

Price per night from

$400

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

Match: Boat available Pets allowed

All filters match

Price per night from

$457

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

Match: Boat available Pets allowed

All filters match

Price per night from

$400

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Boat available Pets allowed

All filters match

Price per night from

$695

Boater's Paradise

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Boat available Pets allowed

All filters match

Price per night from

$376

Match: Boat available Pets allowed

All filters match

Price per night from

$262

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Boat available Pets allowed

All filters match

Price per night from

$326

These homes match some but not all of your filters. Clear all filters

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$440

BAYSIDE CONDO WITH BOAT

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Want to go back” We just got home from our vacation in this apartment. We loved it. Jay took great care of us and was quick to help with any problems or needs. We rented the boat with the apartment and loved being able to walk downstairs and get onto our boat and out fishing for the day. We enjoyed using the grill on the porch and being able to eat our dinner outside enjoying the weather and views. We will definately return again. Thanks for a great vacation Jay.

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$428

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$463

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$144

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,088

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$859

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$401

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$630

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: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$400

“Perfect” Great house. Very clean and simple. You share the beach and dock with the two other houses in the property but was never an issue. Location is great in Largo. Martha was a great host and very friendly. Will definetly be going back.

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$314

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: Pets allowed, Boat available

1 of 2 filters match

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: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$341

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$559

“Beautiful property” This place is way nicer then the pictures. The property itself is breathtaking and its right on the water with a beautiful deck. I love that we had access to kayaks whenever we wanted. No one else but our party was there. The house seemed pretty clean but I wish it had a quick sweep again before we got there. The barstools had lots of dead flies. Which is weird because we didn’t have any flies around even while cooking outside. I loved that we could fish right off the deck. Just wished there was a pipe outside to wash up before going in. It’s definitely heaven, I woke up at 6 one day and enjoyed the sunrise n watching Dolfins and manitees. I would definitely stay here again.

1 of 2 match: Pets allowed, Boat available

1 of 2 filters match

Price per night from

$314

Viewing 38 of 210
rentals in Florida Keys

×

Also consider