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Vacation Rentals & House Rentals in Florida Keys

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279 house rentals

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranquil. The patio faces south so you don't get blasted with the morning or evening sun making it very comfortable having your morning coffee or evening cocktail while enjoying the view. The owners have put a lot of thought into furnishing and accessorizing the unit. Tess and Mimi were wonderful to work with (Mimi met us at the condo and had great advice on where to eat, what to do...)I have stayed in several condos and this was by far my favorite, if your thinking of staying here you will not be disappointed. I will definitely be back the next time I visit the keys.

Match: Shared outdoor pool (heated)

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Price per night from

$342

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!

Responds fast! avg. 3 hours 12 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$279

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 33 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$231

Large Townhouse in Mariner's Club Resort - 3 BR/3.5 Bath

Tavernier townhouse

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 43 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$342

Ocean-Front Caribbean Home.

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Shared outdoor pool (heated)

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Price per night from

$1,718

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)

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Price per night from

$572

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!

Responds fast! avg. 2 hours 28 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$430

ADVENTURE AWAITS I - MARINER'S CLUB 606 - KEY LARGO RESORT STYLE VACATION HOME

Key Largo townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Match: Shared outdoor pool (heated)

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Price per night from

$602

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Match: Shared outdoor pool (heated)

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Price per night from

$654

Top floor, two bedroom,two bath condo with private balcony,close to the Ocean

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 43 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$315

Newly refinished condo open water views very nice

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 40 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$164

Key Largo Kampground Vacation

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

“Great location and pleasantly surprised!” Romberto's Camprground vacation was definitely more than i expected. There was ample room for my husband and I, the folks were nice and the area was quiet and clean. The marina was convenient (small boats only). There was a small leak in the bathroom in the overhead skylight but it was almost negligible unless it was pouring. we will definitely be back.

Responds fast! avg. 2 hours 59 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$145

Key Largo 2/2 Tropical Daze Oceanfront Condo

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 0 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$228

Dream Escape in Islamorada at Anglers Reef

Islamorada villa

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 45 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$354

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$205

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$321

Escape to Paradise --2 bedroom oceanfront condo on Coco Plum

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Great condo with beautiful ocean views!!!!” We couldn't have picked a better condo and location!! Many great restaurants and bars only a few miles away. The pool was really nice overlooking the beach. The condo was nicely decorated and plenty of room for just the two us. Enjoyed sitting out on the screened in lanai having our morning coffee or in the evening having a cold drink listening to the waves and enjoying the light of the full moon reflect off the ocean. The Keys are truly a paradise and we will definitely be back and would highly recommend this condo and area to stay!!!

Responds fast! avg. 3 hours 32 minutes

Travelers’ Choice award

Match: Shared outdoor pool (heated)

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Price per night from

$230

Ocean View Penthouse

Tavernier condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 40 minutes

Travelers’ Choice award

Match: Shared outdoor pool (heated)

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Price per night from

$241

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

Key Largo villa

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$224

Breathtaking Views on Water !!

Key Largo house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 15 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$236

8c, Efficiency located 50 yards from Ocean

Marathon studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 31 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$189

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$294

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

Match: Shared outdoor pool (heated)

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Price per night from

$197

Paridise Found

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 13

Match: Shared outdoor pool (heated)

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Price per night from

$771

Newly remodeled family home with a shared swimming pool and fitness center!

Stock Island house

3 bedrooms / 3 bathrooms / sleeps 6

“Cute place” Excellent home and a gated community with great amenities. Exercise room and gated pool are clean and well kept.

Responds fast! avg. 2 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$453

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 31 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$201

Paradise on Cudjoe Bay

Cudjoe Key house

2 bedrooms / 3 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$351

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

1 bedroom / 1 bathroom / sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$212

$2500 A MONTH FOR OCTOBER AND NOVEMBER. OCEANFRONT 2 BEDROOM/2 BATH CONDO

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing view! Absolutely gorgeous!” My two teenage daughters and I stayed at this condo and it worked out perfect for us! The view is stunning, and I loved to just sit in the living room and look out at the ocean. The condo was very clean, and really nicely decorated. There were some beach chairs on the balcony that we used at the beach which was nice to have since we had flown to Florida. There were also beach towels to use. The kitchen was cute with everything you would need to cook, although we mainly just ate breakfast there. It is located away from traffic so nice and quiet. I swam in the pool once and it was warm like a bathtub. Felt good after a day at the beach. This was our first trip to the Keys, and I liked that we were centrally located. We were a couple hours from Fort Lauderdale where we flew in from, and a couple hours from Key West where we went for a day trip. We loved John Pennekamp State Park which is only about 20 minutes away, and swam with a manatee at Canon Beach. We also snorkeled with Robbie's in Islamorada which is 20 min. the other way from us. I would definitely stay there again if I return to the keys.

Responds fast! avg. 1 hour 47 minutes

Travelers’ Choice award

Match: Shared outdoor pool (heated)

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Price per night from

$139

OCEANFRONT CONDO WITH ALL AMMENITIES!

Tavernier apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great place for a comfortable vacation” We had a wonderful time at this Ocean Pointe condo. The facilities are fantastic. The pool is very clean. The condo was like new. The complex is staffed 24/7. We felt very safe and comfortable. The ocean side view is great. We would not hesitate to return another time.

Responds fast! avg. 2 hours 25 minutes

Travelers’ Choice award

Match: Shared outdoor pool (heated)

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Price per night from

$269

Our Kozy Key - Paradise FUN at your door.

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Cozy and Convenient” The townhouse was located right outside the pool and private lagoon which was perfect for traveling with small children. The place was clean and fresh smelling and the decor is bright and inviting as a beach house. There were more than expected amenities which made our stay as comfortable as being at home.

Responds fast! avg. 3 hours 6 minutes

Travelers’ Choice award

Match: Shared outdoor pool (heated)

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Price per night from

$287

Waterfront in Key Largo, Terrific 1/1 Apt, 2nd Floor, Pet Friendly, Sleeps 4

Key Largo apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 25 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$80

Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 35 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$289

LUXURY HOME WITH DOCK, POOL, HOT TUB, AND ELEVATOR

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“WONDERFUL” Where to start…Larry was at the home when we arrived and took the time to show us everything we needed to know about the systems in the house and how to use the elevator..Daughter and her husband joined us from Wyoming and I must say it was the best vacation we have had…The house is immaculate and we had a wonderful 7 days….We would walk to the top deck and enjoy the sunsets with a fine glass of wine….you could not ask for better views from any where on the property, pool.dock or balconies…We caught fish off the dock, snapper etc….We left with memories that we will never forget…Thanks Larry for sharing your home with us ….It was worth every penny and we hope to visit again…The pool and hot tub was used everyday and they were both relaxing after a hard day… Thanks again, Jim and Mary

Match: Shared outdoor pool (heated)

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Price per night from

$492

Enjoy the Florida Keys!

Tavernier condo

1 bedroom / 1 bathroom / sleeps 2

Match: Shared outdoor pool (heated)

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Price per night from

$184

House on 7th ST in KEY Colony Beach W/CABANA CLUB

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 23 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$228

Key West home w/shared pool and just steps from historic Old Town

Stock Island house

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 2 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$415

LISENCED MGR! BRAND NEW & TOTALLY RENOVATED 2/2 SUITE! OCEANFRONT BEACH RESORT!

Key Largo apartment

2 bedrooms / 2 bathrooms / sleeps 6

“A great location for accomplishing our interests while visiting” This rental was a perfect set up for two people - also very clean, convenient and seeing the egret's nest outside the patio was special. The beach chairs in the closet need attention as it was nice to have Harry Harris park near by. Thank you.

Match: Shared outdoor pool (heated)

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Price per night from

$206

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