Holiday rentals with a pool in Stock Island

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Popular amenities for Stock Island rentals with a pool

House rentals with a pool

Top guest favourite
Home in Marathon
4.99 out of 5 average rating, 138 reviews

Cancellation Deal: 08/02 thru 08/09

ShelleyRating, 5 stars1 week ago
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!
Guest favourite
Home in Cudjoe Key
4.97 out of 5 average rating, 160 reviews

Cudjoe Key Home with a View

YirenyRating, 5 stars2 weeks ago
The house is located in a peaceful community with a store inside that was perfect because you don’t have to drive to get basic necessities. Pool and spa were perfect. And the view is magical. The house was cleaned and beautifully decorated. The outside areas were perfect too. I loved take breakfast on the porch.
Guest favourite
Home in Cudjoe Key
4.93 out of 5 average rating, 178 reviews

106 Newly Renovated House with Oceanview and Pool

JoanRating, 5 stars1 month ago
As always, Michael’s place was spotless, perfectly stocked and just as pictured. We come back here annually to fish at Sugarloaf Marina and are always satisfied. Michaels house is in the perfect location, with the best sunsets, an amazing dock and pool, and the house is always stocked and we're able to relax for another day of tarpon fishing.
Guest favourite
Home in Key Colony Beach
4.95 out of 5 average rating, 117 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

LaurenRating, 5 stars1 week ago
Clean house, well decorated, great location and responsive hosts! It’s also a plus that they accept pets for a reasonable pet fee. Key Colony Beach is a great location and this is a lovely little home. Book with confidence!
Guest favourite
Home in Key West
4.92 out of 5 average rating, 13 reviews

Oceanfront, Resort-like luxury home with private p

OliviaRating, 5 stars4 months ago
Was such an amazing place. My family loved it. My dad was thrilled with it which he’s normally the one that’s the one we need to impress. He’s never really liked going to Keywest because of how busy it is. This spot and location he absolutely LOVED. Which made all of us happy. The house is gorgeous and massive. The pictures don’t do the place justice. Super peaceful, relaxing and just a beautiful layout. We were 10min from town and sooo much to do around our area if we didn’t feel like going into the main town. Very pleased! We will be back for sure. Even my father’s words! He has a new appreciation for Keywest! Thank you Javier for everything!
Top guest favourite
Home in Key West
5 out of 5 average rating, 15 reviews

Kittyhouse on Catherine, Tropical Pool, Parking

AmandaRating, 5 stars1 week ago
2 adults and 2 teenage boys loved this home. There was room downstairs for us all to be together when we needed a break.Alan responded immediately to any questions. The pool was a lifesaver on these hot and humid days. We loved that he had towels for us to use. We would surely stay again.
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 12 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

HansRating, 5 stars1 month ago
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended
Superhost
Home in Cudjoe Key
4.83 out of 5 average rating, 266 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

FrankRating, 5 stars6 days ago
We had a great time at Janet and Jerry’s home at Venture Out in Cudjoe Key! We made the short drive down to Key West after some morning pickleball. Our only unexpected (not welcome) surprise was the rotten egg smell all the way down the Keys. The smell is apparently from the over abundant seaweed blooming due to very warm water temps. Unfortunately this is a norm between May and October now? Key West did not have the smell due to wind direction, so overall we really enjoyed our stay!

Apartment rentals with a pool

Superhost
Apartment in Key West
4.83 out of 5 average rating, 276 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

MichaelRating, 5 stars1 month ago
Right next to Duval Street, easily walkable to major attractions, restaurants, bars.. Host was super responsive, friendly, and really worked with us on anything we needed.. Great place!
Guest favourite
Apartment in Key West
4.95 out of 5 average rating, 19 reviews

Chagall’s Corner | Newly Remodeled!

AshleyRating, 5 stars3 weeks ago
Woooow, this place was nothing short of amazing!! The exact amount of space we needed because we knew we would be out and about most of the day!! Bed was very comfortable and ushered us right to sleep after our flight! Walking distance from literally everything we had on our list to do! We mingled with the locals, listened to live music during dinner, enjoyed the beach at sunset, and learned a little bit about the Bahamian history! This place is literally 2or 3 blocks from the southern most point and the best Cuban coffee at a local restaurant/food truck! 10/10 would definitely recommend!! Already planning our next visit!!
Guest favourite
Apartment in Key West
4.95 out of 5 average rating, 39 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Lori Rating, 5 stars1 month ago
We are absolutely in love with this place. The views are gorgeous. the grounds were immaculately groomed. There are so many colorful trees and flowers. The pool is slightly heated, which is perfect. Everyone we met was so nice and helpful with recommendations. We got to see the jets fly over a few times, so cool. The kitchen has everything you need to prepare meals and snacks. The beds in both rooms are very comfortable. We hope to stay here again in the future.
Superhost
Apartment in Key West
4.86 out of 5 average rating, 29 reviews

Rum Cay at Sunrise Suites

LineRating, 5 stars2 days ago
Beautiful place ,quiet even if the airport is close bye but it’s not busy. Farley close with car yo everything. They had everything you needed in the apartment and it was very clean.
Guest favourite
Apartment in Key West
4.78 out of 5 average rating, 299 reviews

Affordable Beachfront Luxury Condo Sleeps 6

SharonRating, 5 stars1 month ago
Traci’s condo was great in every way! Everything was very clean and the view was amazing. We could enjoy watching the turquoise water and swaying palm trees from almost every room – both bedrooms, living room, kitchen, dining area, or relaxing on the large balcony. Some of the furniture is different in the photos, but my group agrees it is even better now than what you see. Having our own parking space in the garage was much appreciated, too. Traci responded quickly; clear check-in instructions. We would definitely stay here again.
Guest favourite
Apartment in Key West
5 out of 5 average rating, 7 reviews

Hyatt Beach House-Quiet Key West Spot!

AnneRating, 5 stars2 months ago
Close enough and not too far away from Key West exploration. The concierge was friendly and very eager to accommodate, front desk staff were helpful and very pleasant. The restaurant next door, Tavern N Town at the Beachside Resort, had a nightly happy hour with great cocktail service from Mr. George and delicious tapas - shrimp tacos, conch chowder, calamari, roasted cauliflower. The rental was fully stocked with all dishes & utensils needed. No issues with parking or anything else. Very enjoyable stay.
Guest favourite
Apartment in Key West
4.89 out of 5 average rating, 93 reviews

The Island Suite @ KW vacation

VirginiaRating, 5 stars1 month ago
Key West is expensive so this wasn’t exorbitant for the area. From here, we could walk to every attraction and restaurant in Old Town, including the dock to board a sailing ship to catch a magnificent sunset. The lodging is in an old house turned old hotel. It was very comfortable for 2 people. The dedicated porch overlooking the beautiful garden with gurgling fountains was a highlight. There was a nice black cat who sat with us every time we were on the porch. There is an outdoor gathering area below the porch that guests from surrounding units used. They were a bit loud; but, it’s Key West. The only real negative is a lack of nearby parking. There is supposed to be a 15 minute unloading space in front of the building but the same car stayed in it for 2 days. We found a spot on the street about 4 blocks away. I strongly recommend getting any groceries you may want (except fresh fish) before you arrive. We mostly ate out.
Top guest favourite
Apartment in Marathon
5 out of 5 average rating, 20 reviews

*NEW* Private Beach, pool & fully loaded kitchen

JamesRating, 5 stars1 month ago
Our first time visiting the Keys and Celia’s place made it wonderful! Located in a very nice, quiet, and safe community her condo is like new and so well cared for. Perfect size for our two couples. The decor and furniture is very nice, bright and clean. Had all the amenities we needed and then some. We enjoyed the heated pool everyday and the private beach was nice for a more natural experience. The furnished patio had a great view of the pool and ocean. Celia is a wonderful host! Very helpful and a great communicator.

Quick stats about holiday rentals with a pool in Stock Island

  • Total rentals

    320 properties

  • Nightly prices starting at

    ₹7,738 before taxes and fees

  • Total number of reviews

    11K reviews

  • Family-friendly rentals

    250 properties are a good fit for families

  • Pet-friendly rentals

    100 properties allow pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

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