Vacation Rentals & House Rentals in Key West

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92 house rentals

The Water's Edge

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do during your Key West experience. Ocean Paradise has gorgeous views from the 3rd level balcony, a wonderful screened-in porch on the main level (perfect for al fresco dining), and an incredible pool area with a larger than expected private pool and stunning landscaping that provides both shade and privacy. The home's interior is both spacious and functional, including lovely furnishings and everything you need for a memorable vacation in beautiful Key West. Just as important to us was the ease in managing our visit to Ocean Paradise. The owner and his staff were absolutely incredible to work with throughout the entire rental process. We had originally scheduled our visit for the 2014 Thanksgiving holiday week. However, a need arose which required us to cancel that planned stay. The property owner was gracious enough to work with us in our desire to reschedule our visit for May 2015, demonstrating a focus on and respect for his guests throughout the entire process. Our Key West vacation, and specifically our week-long stay in Ocean Paradise, was undoubtedly a memorable experience for me, my husband and our two adult children (as well as the little "furry" member of our family who also joined us for our Key West adventure). We will be returning to Key West, and when we do, Ocean Paradise will be our chosen "home away from home" during our stay!

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Price per night from

$842

Admiral's Lane

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“Fabulous family rental” We have stayed in Key West for four years now. This was the best rental property so far. The location is perfect for beach days and walking both ends of Duval at night. The property itself had all the amenities we needed and was run well by the property managers. The major reason we didn’t give five stars is that all of the tv’s were from the 90’s. They offered cable but on screens that are archaic. Not great for unwinding or catching up with March Madness. For this level of home/rental, the owners could spring for even just ONE flat screen.

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Price per night from

$625

The Mermaid's Garden

Key West house

4 bedrooms / 5 bathrooms / sleeps 8

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Price per night from

$625

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 33 minutes

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Price per night from

$1,797

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!

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Price per night from

$750

Island Style

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$769

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.

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$107

Seaside Place Key West FL 5 Bedroom House 4 Baths

Key West house

5 bedrooms / 4 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

Responds fast! avg. 3 hours 15 minutes

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Price per night from

$1,260

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$107

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 46 minutes

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Price per night from

$326

** Fantastic Spring& Summer Stay Downtown walk everywhere **

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$366

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.

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Price per night from

$100

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$515

tropical Casita

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$107

Poinciana House

Key West house

1 bedroom / 2 bathrooms / sleeps 4

“Awesome” The house was just as Historic Hideaways pictured and described...beautiful. The house was very clean, a pool service came twice a week to clean the pool and Tim, (agent) was very informative and helpful. Everything was supplied from towels to suntan lotion. There was nothing we needed to bring except our clothes & food. I would definitely stay here again.

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Price per night from

$385

Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Fabulous luxury home in Fabulous Key West” Beautiful, private, historic 2 BR/2 bath home, lovely heated pool, outdoor dining & living areas in addition to most attractive indoor spaces. Wonderful Old Town neighborhood. Can walk, cycle, & Lyft everywhere (including great restaurants)--no car needed. 2nd BR is in the guest house beyond the pool--fabulous outdoor shower completes the "only-in-Key West" ambiance. The owner, Kim, is super responsive.

Responds fast! avg. 2 hours 49 minutes

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Price per night from

$557

Conch Republic Retreat

Key West cottage

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$107

** Totally Renovated Ocean View Condo Great Prices **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$602

Key Lime Pie

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Loved Off Season Key West” Spent a month in this very secluded house within walking distance of everything, including the marina, Duval Street and my favorite Watering Hole, Finnegan's Irish Wake pub. Renting in October, the off season, meant I got to experience an uncrowded Key West. And best of all, at the end of the month, to experience Fantasy Fest in its entirety. What a rush. House was wonderful. Had it all including a hot tub. Private parking, a real plus in Key West. Plan to do it again.

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Price per night from

$87

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$572

The Meadows House

Key West house

2 bedrooms / 3 bathrooms / sleeps 4

“The Meadows Home- wow !!!” Tim, Thank you so much for your help in booking The Meadows Home. I have to say when I was booking the home, I was a little afraid of the pictures I saw on line. The pictures do not do justice to show the beauty of the home and the pool... Wow!!! My in-laws went back home to Poland toady they couldn't stop talking about what a great time they had in Key West and what a wonderful time we had in the house, swimming and drink by the pool. I really hope my family and I can return and visit the home again. Best Wishes, The Zatek Family

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Price per night from

$350

Flagler Station

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

“Little gem is right!” Can't say enough good about this place! Newly renovated 1800 square foot home;3 be king in master, queen and double Beds in third room. Loved the small private pool and gourmet kitchen, much thought, love and detail went into making this a home away from home. 5 blocks from the public beach and a couple of miles from duval street. So close to so much but still have some privacy and parking.. Would love to bring bikes next time. Y'all save a place for me next summer we hope to come back! And the home away folks get an A plus for the process of renting, it was so easy...

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Price per night from

$107

Perfect Pineapple

Key West house

2 bedrooms / 1 bathroom / sleeps 4

“Kudos to Owner” The owners updated many things such as new bathroom tile, area rugs, washer and dryer area as well as painting. Still needed are more dinner and salad plates as it is necessary to run the dishwasher almost every day. The timer system for the garden lights needs to be repaired. Guests came to visit and it was very crowded with 4 people even with two bedrooms. This is a perfect place for a couple. The big negative is the Iguana's who wander from the cemetery area . A 3 1/2 foot Iguana can scare the heck out of you.

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Price per night from

$100

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!.

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Price per night from

$335

Easy Livin'

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Great Experience” This house was beautiful. The pictures don't do it justice. It's the perfect house for families. The location couldn't be better - walking distance to everything.

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Price per night from

$550

* Book today Anchor drop key west short bike ride from old Town*

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$658

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Outstanding!” 1800 altantic was the perfect place to stay for our "friends" reunion. Our condo was clean and well equipped. The place was extremely safe and secure.

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Price per night from

$686

Rosalie's House

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$167

Tropical Dreaming

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Oasis in busy Key West” We have stayed at Tropical Dreaming several years in a row. It is a lovely setting a couple of blocks off Duval so it is its own oasis.

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$365

Poolside Paradise

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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$100

Valhalla

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Best Vacation Ever” This home is really lovely and larger than we expected, having never been in a 'shotgun house'. Kitchen is small but fully functional w dishwasher etc. The house has everything you need (beach towels, laundry detergent, TP, etc) and the quality is great, eg crate & barrel dishes... The pool area is totally private, peaceful, and really quite beautiful. Never saw any neighbors, heard them once or twice but they were very quiet. Mgmt company was approachable and accomodating. We were there with our 2 teens, lots to do. Because KW is a party town and everyone sleeps late, we had no late morning parking dilemmas at the beach, unlike Sanibel. Wish we could have stayed 2 weeks. Can't wait to come back so our only concern is...if we are honest in our review, will Valhalla be available?

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Price per night from

$450

** New Ownerss many upgrades, Tropical retreat on the ocean**

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$572

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Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$573

The Dolphin House

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“Perfect” Perfect house. Perfect pool. Perfect location. I want to live there. Secluded but so close to everything!

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$550

Here Tomorrow

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

“Exceeded our expectations” We loved this house! Super location - just one block off Duval - and also near to the beach; we went to the Southernmost beach a lot. We thought that the house is bigger then it looks in the photographs. We were expecting a small little conch cottage whereas we got a nice size 3 storey house. The bedrooms in particular were very roomy and of course the main bathroom with the jacuzzi bath, the doublesize waterfall shower (with sit down area) and double vanity area was fabulous. It had all the expected amenities and we made particular good use of the ice machine for cocktails by the pool :-) Decor is modern. Very nice bed linen and lots of towels were provided. The pool area was a little small (but no smaller then we expected from the photographs). Was not great for sunbathing as the sun only hits in one spot but as I mentioned earlier we went to the beach a lot. All in all a great house. Also must mention the good service from At Home in Key West when booking. I found the Live Chat service really useful. We had no need to contact them during our stay (no issues with house etc) so cannot comment on service during our stay. Eating: We ate at out the majority of the time and aside from the fish we caught (we went fishing with Captain John's Greyhound V) we never cooked at home. Our favourite place is A&B lobster house/Alonzos, Santiagos Bodega and Firefly. Shopping: Coach and Banana Republic on Duval are probably the only two good stores - only you are looking for tee-shirts!!!! Red Gallery near Flagler Station museum is good for quirky gifts. Recommendations things to do: Custom House Museum Lighthouse tour Little White House Hemingway House Fishing with Captain John's Greyhound V is always good

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Price per night from

$117

** Totally renovated in 2019, New Kitchen & Bathrooms.. Book Now **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$601

* Key West Beach Condo Casa Coastal East Fantastic monthly pricing *

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

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$134

Kemp House

Key West house

3 bedrooms / 4 bathrooms / sleeps 6

“Perfect little resort” The Kemp House was warm and inviting after Our team of ladies finished our Ultramarathon relay. The pool and courtyard were the perfect place to unwind. Plenty of room for everyone! Perfect location a block from the seaport and two more to Duval. Air conditioner wasn't blowing cold air in the one room but contacted Historic Hideaways and they sent someone within a half hour to fix/replace it! It's a perfect little private resort...We will definitely be back!

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Price per night from

$689

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