
Vacation rentals with a pool in Big Pine Key
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Top-rated rentals with a pool in Big Pine Key
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Popular amenities for Big Pine Key rentals with a pool
House rentals with a pool

Pelico Palms Sunset Suites
fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!

Casa Calypso 3bed3bath sleeps 8 beautiful decorate
We had a great time at Judy’s airbnb. It was super nice, clean and had really comfortable beds. The pool was right across the parking area, very clean, private and always had chairs available. Over all our stay was great and we will definitely be back.

Catherine House: A charming Old Town Key West
We thoroughly enjoyed our stay at the Catherine house and it was a perfect location to explore Key West. Beautiful space and well thought out. Perfect for two couples! A welcome retreat when you wanted to get out of the Key West hustle and bustle. We loved our time there!

P22 - Updated 3 bedroom 2 bath duplex with private
We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.

Golf Coast Oasis
This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage
It really is the perfect place to stay. We picked this house after our last trip to FL where we rented a beach house only to have high winds and man of war jellyfish so couldn't get in the water at all. This place with its amazing hot tub and pool, tons of pool toys and floaties, books and games, would be a wonderful vacation even if you were stuck there the whole time due to bad weather, These owners have done a wonderful job thinking of so many amenities- cozy couch blankets, life jackets, tons of beach equipment, so many dishes and pans and various drink holders. The only complaint I could think of if I had to would be to have another ice tray (there were two semi broken ones but not a big deal as we just bought ice). But that's a pretty small thing in the long list of things that were superb. Even the beds were as soft and as comfortable as mine at home. I hate to let the secret out, but this house is fantastic.

Sale! Pool, Hot Tub, Dock & Putting Green!
We had an amazing time! The location is perfect with so many things to do, pool, hot tub, canal, etc. The home was overall beautiful and we loved every second of it!

Islamorada Reef Canal & Pool home off Tav Creek-
Isa was an amazing host! The house is beautiful and pristine! We loved the pool and how close the house is to everything. Our only regret is we couldn’t stay longer!!!! Thank you so much!
Condo rentals with a pool

2 Bedroom Oceanfront Complex Heated Pool KCB
We had a great time! Awesome community with walkable restaurants and bars. We loved the local beaches. The people at the complex were super nice. Our four boys loved running from the pool to the beach. Everyone we met was very nice. Great instructions and recommendations. Loved it!

Resort Condo: Pool | Beach | Marina | Pickleball
This place was great for an in between Miami and Key West! The pool was perfect for relaxing at all day! Restaurants near by were all fantastic! Doable drives for day trips to key west and Miami!

Oceanfront 3 bed condo Ocean Edge w/ optional slip
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.

1BR - Key Largo Sun & Sand Hideaway
Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.

Top floor Ocean Views, Spacious 2 Bedroom Condo, V
This was our first time in Key West. We wanted to stay a little tucked away from the downtown bustle. The complex is beautiful with great amenities. And it’s close enough to shopping, restaurants and bars! We definitely plan on booking the same place in the future!!

Tropical Escape at Sunrise
Eric’s place was lovely, well maintained, nicely appointed, and immaculate. The 3 of us enjoyed the balcony overlooking the pool. Even though the apartment is near the airport we only heard planes twice in the 4 days we were there. There is a convenient little grocery store on the site and excellent BBQ from a food truck near the pool. Eric responded to our questions promptly. Comfy beds, everything worked and we enjoyed our stay. Would stay here again.

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Kimberly was a very responsive host providing clear instructions, local recommendations and checking in on our stay to see if she could help with anything else. The unit was clean and comfortable. Wish the deck was larger was our only negative. The community pool area was great to hang out at with plenty of chairs, lounges and umbrellas. And we enjoyed the poke bowl and cocktails at the on-site grill. Would stay again if in the area.

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again
Quick stats about vacation rentals with a pool in Big Pine Key
Total rentals
130 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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