Vacation Rentals & House Rentals in Florida Keys

Updating...

age 0-16
432 Results

Relevance

Price: low to high

Price: high to low

Reviews

432 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: Clothes dryer Swimming pool

All filters match

Price per night from

$343

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

Key Largo townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$688

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

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$916

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

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$287

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$333

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: Clothes dryer Swimming pool

All filters match

Price per night from

$344

Duck Key 50% off October

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$659

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$230

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$655

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!

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$659

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

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$1,147

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

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: Clothes dryer Swimming pool

All filters match

Price per night from

$286

Responds fast! avg. 2 hours 44 minutes

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$247

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$344

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$373

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$791

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

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$224

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$258

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$622

BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking

Key West house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$2,121

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$573

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: Clothes dryer Swimming pool

All filters match

Price per night from

$435

“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

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$671

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: Clothes dryer Swimming pool

All filters match

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: Clothes dryer Swimming pool

All filters match

Price per night from

$254

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$247

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: Clothes dryer Swimming pool

All filters match

Price per night from

$207

Responds fast! avg. 1 hour 39 minutes

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$803

Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$573

Beautiful Captain's Cove

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$573

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$356

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

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$917

Luxury condo overlooking harbor with ocean view

Islamorada condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$391

Kokomo Cove Boat House

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$401

Experience the Florida Keys like never before!!!

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$246

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$1,948

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

Key Largo hotel apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Clothes dryer Swimming pool

All filters match

Price per night from

$402

Viewing 38 of 432
rentals in Florida Keys

×

Also consider