Vacation Rentals & House Rentals in Florida Keys

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145 house rentals

Canal-Front 3BR w/ Private Pool, Boat Slip, Tiki Hut & Kayaks - Near Beach

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$179

Tropical Escape

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.... No complaints.

Match: Private outdoor pool (unheated)

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Price per night from

$247

Private Beachfront Paradise

Matecumbe Key house

4 bedrooms / 3 bathrooms / sleeps 8

“Nicest rental property we have ever stayed in!!” Beautiful home on spotless white beach! Property has been updated with upscale furnishings throughout. Granite, leather furniture, redone bathrooms. Well stocked for all your vacation needs -- towels, beach chairs, beach toys, kitchen full of everything you need, 2 grills. Outside patio was amazing for our meals, sunrises and after dinner activities. The backyard was the beach filled with palm trees for natural shade. Hammock and volleyball court, beautiful pool with waterfall, tables and chairs everywhere for meals or for just relaxing. We traveled as two families and there was more than enough room for all of us. We felt right at home right away. Highly recommend this paradise!

Responds fast! avg. 3 hours 24 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$603

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

Match: Private outdoor pool (unheated)

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Price per night from

$236

President's Walk

Key West house

2 bedrooms / 1 bathroom / sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$195

Gorgeous, recently-updated, waterfront home w/ beach, pool, dock, & kayaks

Duck Key house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 40 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$771

Waterfront house w/ covered patio, private pool, & 75 ft. dock - dogs welcome!

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 40 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$134

Canal-Side 4BR Home w/ Large Private Dock, Covered Patio & Waterfront Pool

Key Colony Beach house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$344

Big house

Key West house

5 bedrooms / 5 bathrooms / sleeps 12

“Bachelorette in Key West” I rented this house for my sister-in-law's bachelorette weekend in Key West. The house was spacious, clean, and overall the best place I've ever stayed! It was worth every penny!

Match: Private outdoor pool (unheated)

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Price per night from

$705

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 2 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,562

Oceanfront Oasis with Quintessential Island Living

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 11

“Relax in Luxury” Great Location. Lots of nearby restaurants. Owners were extremely helpful in recommending attractions. A stunningly beautiful home with plenty of room for my large family to spread out. Pool was great. Swimming in warm shallow waters off of our own private beach was perfect for the kids. Pictures don't do it justice. Plenty of amenities - snorkeling gear, paddle boards, kayaks, pool toys, karaoke machine, portable waterproof sound system, etc. I have been to Florida many times always renting houses. This was by far the best.

Responds fast! avg. 3 hours 40 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,723

TWICE THE CHARM

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$183

LYONS LANDING

Islamorada house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$262

Paradise In Marathon, FL Keys Large Oceanside Home

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“Wonderful property. We had a great stay!” Super close to publix and boat ramp ($30 fee in and out) so convenient. Very nice accommodations. Wonderful to have the boat right out back

Responds fast! avg. 2 hours 17 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$401

Islamorada Paradise

Islamorada house

3 bedrooms / 4 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$690

Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!

Stock Island house

3 bedrooms / 2 bathrooms / sleeps 10

“What a fun time !!!” I brought my daughter & her boyfriend, my middle daughter and her boyfriend, my son who is a freshman at psu, my girlfriend suzie & myself. We golfed( great golf course ) !!! We jet skiied around key west... you guys have to do this!!! great and wonderful guides, we chartered a boat for a three- four hour tour. we all caught fish. & one was for dinner:) black fin tuna, and a trophy fish 5' 6" barracuda;) !!! The people were friendly, the atmosphere was warm and cozy. The Pool was great, The rooms were more than enough. Easy access to Duval street. Many clubs and eateries on duvalt street. The books left on the counter tops for things to do were very very very helpful. The night life is fun. and everybody was very friendly and helpful...I will be back with my family

Responds fast! avg. 40 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$410

Clean Keys 3/3 w/Davits Clear Canal Bay Side/Views Fenced 2Level Tavernier Home

Tavernier house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 1 hour 53 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$173

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$193

Gated Canal-Front 4BR w/ Hot Tub, Heated Pool, Gourmet Kitchen & Boatslip

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$366

TROPICAL OASIS

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$292

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$107

Key Largo Paradise Point ! CALL FOR SPECIALS!!!

Key Largo house

3 bedrooms / 2 bathrooms / sleeps 6

“LOVE! LOVE! LOVE!” I really loved this place for my family! We saw a ton of manatees right from the dock. We loved having coffee and breakfast and watching them from the deck. The house was perfect...comfortable and clean with all the amenities. And even though we brought our kayaks, they had great ones there. Can't wait to go back!

Responds fast! avg. 3 hours 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$339

Sunshine Key West

Key West house

2 bedrooms / 3 bathrooms / sleeps 5

“Perfect Home for Key West” This place has all the amenities you need! It was our first time renting a home and it couldn't have been more perfect! Quiet neighborhood, but not too far from the action of Duval.

Match: Private outdoor pool (unheated)

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Price per night from

$107

Executive Bay Townhouse w/Heated Pool, Private Beach, Tennis, Fishing Dock & nea

Islamorada apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Great condo, perfect location!” I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close to everything. The property management service was excellent. We had a wonderful family vacation and will definitely be returning next year!

Responds fast! avg. 3 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$103

FLAMINGO COTTAGE

Islamorada house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$100

Verandah

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“We had a delightful stay, enjoyed meeting warm and welcoming peo” This was our second year at verandah and once again it was just perfect. Can't wait to return in 2014. Key west is definitely our happy place.

Match: Private outdoor pool (unheated)

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Price per night from

$100

Coconut Cottage

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$77

CONCH BAR SOUTH

Tavernier house

4 bedrooms / 3 bathrooms / sleeps 10

“Great property but poor experience with realtor” We rented for the month of November with 9 people in our party. The property and home are beautiful but we unfortunately did not have a very good experience withKeys Holiday rental department. One of the main reasons we rented the house was the use of the boat davits but two weeks before our arrival I was informed the davits were being removed. I was left with no choice but to buy additional fenders to protect my boat from those crazy Keys winds of 25+ MPH. There were only two chaise loungers for a house that rents to large families, both were broken. When we informed the realtor they had them removed "for our safety" but informed us they would not replace them. I purchased their damage insurance yet they tried to pin me for the cost of a table that was already broken when we arrived. So they decided to deduct $50 from our security deposit for "additional cleaning". Nice house, but will never use Keys Holiday Rental firm again.

Match: Private outdoor pool (unheated)

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Price per night from

$317

SPECTACULAR Waterfront Key Colony Beach Home w/Heated Pool & Dock

Key Colony Beach apartment

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$1,157

Responds fast! avg. 29 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$253

Conch Republic Retreat

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (unheated)

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Price per night from

$107

HOUSE DORADO

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$617

Luxurious Key Largo Family Home with Pool & Large Dock

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$272

Gulf View Place w/ Dock, Pool, Kayaks, Sandy Shore

Marathon house

4 bedrooms / 4 bathrooms / sleeps 10

“Awsomely relaxing yet centrally located for easy day trips.” Very clean and nicely equipped with everything needed for a relaxing and comfortable at home feel vacation. Lots of room for family reunions. Centrally located in the Keys so day trips either north or south are easy. Don't miss Savannah Sweets Bakery and Cafe for the best key lime pie. Property manager a phone call away but never needed as everything was in good working order. Owners very nice and have thought of everything. Pool more of an oversized hot tub but does the trick on hot days. Can't wait to return!!

Match: Private outdoor pool (unheated)

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Price per night from

$492

tropical Casita

Key West house

1 bedroom / 2 bathrooms / sleeps 2

Match: Private outdoor pool (unheated)

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Price per night from

$107

MANATEE MANOR

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$198

Amelia Home

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect” We loved this house! It was the perfect little getaway. It was in a great location, very convenient to everything. The house was beautiful with very nice decorating inside to the beautiful lush garden outside. If we visit Key West again, I’d stay here without hesitation. I highly recommend!.

Match: Private outdoor pool (unheated)

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Price per night from

$330

Gulf View Suites w/Docks, Pools, Kayaks -Sleeps 20

Marathon house

8 bedrooms / 6 bathrooms / sleeps 20

“Awesome location, close to many popular destinations.” My husband and I really enjoyed our vacation to Marathon Fl. Our vacation home was very clean and close to many great restaurants and beaches. We used the kayaks, swam in our own pool and sat out on the deck to just watch the world go by. We would highly recommend Rent My Island.

Match: Private outdoor pool (unheated)

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Price per night from

$950

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