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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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$179
“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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$247
“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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$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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$236
Match: Private outdoor pool (unheated)
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$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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$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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$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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$344
“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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$705
Responds fast! avg. 3 hours 2 minutes
Match: Private outdoor pool (unheated)
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$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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$1,723
Match: Private outdoor pool (unheated)
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$183
Match: Private outdoor pool (unheated)
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$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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$401
Match: Private outdoor pool (unheated)
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$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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$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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$173
Match: Private outdoor pool (unheated)
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$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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$366
Match: Private outdoor pool (unheated)
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$292
Match: Private outdoor pool (unheated)
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$107
“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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$339
“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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$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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$103
Match: Private outdoor pool (unheated)
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$100
“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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$100
Match: Private outdoor pool (unheated)
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$77
“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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$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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$1,157
Waterfront/Open Gulf Access/Dock/Pool/Spa/Wraparound Deck View of Sunset,Sunrise
Marathon house
3 bedrooms / 2 bathrooms / sleeps 8
Responds fast! avg. 29 minutes
Match: Private outdoor pool (unheated)
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$253
Match: Private outdoor pool (unheated)
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$107
Match: Private outdoor pool (unheated)
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$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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$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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$492
Match: Private outdoor pool (unheated)
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$107
Match: Private outdoor pool (unheated)
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$198
“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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$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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$950