Holiday rentals with a pool in Summerland Key

Find and book unique homes with a pool on Airbnb

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Popular amenities for Summerland Key rentals with a pool

House rentals with a pool

Superhost
Home in Cudjoe Key
4.85 out of 5 average rating, 52 reviews

Keys getaway

JamiRating, 5 stars2 months ago
We were there to celebrate my husband's 50th birthday. The master bed, pillows and linens were very comfortable. The screened in porch with plenty of comfortable seating was our favorite amenity of the property. We hope to rent there again when we are back in the area. Very comfortable and very clean. 😁
Superhost
Home in Cudjoe Key
4.88 out of 5 average rating, 59 reviews

Cozy 2 br/2 bath home in Cudjoe

MariannRating, 5 stars1 month ago
Marcela's place was exactly as described and very clean. One master bedroom with master bath, and another bedroom with a twin/trundle bed, and sofa in living room. Kitchen had good amenities with cutlery and glasses, etc. We didn't use the washer but the dryer was very handy for drying bath towels and pool towels. We sat outside in the back yard the first night and heard a mysterious animal call, we thought it was a bird but then using google we found out it was a tokay gecko! So cool. We used the large saltwater pool which was very very nice. It's just a short drive to several great restaurants in neighboring keys, and we made a day trip to Key West which was awesome! I recommend Tonio's Seafood Shack & Tiki Bar, great key lime pie. Forks & Stix is a great little sushi place with great lemonade, Island Fish Company in Marathon had a great outdoor vibe right on the water. Best beach is Bahia Honda State Park. Note there is a $125 community fee upon check-in to the resort.
Guest favourite
Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviews

Sea Turtle Cove

ThomRating, 5 stars2 months ago
Philip's listing described the place perfectly. Zero unexpected surprises and it had absolutely everything to make our vacation super enjoyable. When it comes to location, so much to do in under 30 minutes. Smack dab in the middle when it comes to driving to Marathon or Key West. It was also great to be able to keep a boat right outside and to have a marina as part of the park. Access to great places to fish are 15-30 minutes away.
Superhost
Home in Cudjoe Key
4.63 out of 5 average rating, 166 reviews

Ocean Front Home in Great Location

HaroldRating, 5 stars2 weeks ago
This booking was great for what we needed, thank you to the responsive hosts and pet friendly house that made our vacation that much better.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars3 weeks ago
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars4 weeks ago
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.
Superhost
Home in Cudjoe Key
4.79 out of 5 average rating, 19 reviews

Tropical Island Getaway

DebraRating, 5 stars2 months ago
Place was sweet, kitchen and bathroom well stocked. We didn’t get an opportunity to try the pool or hot tub. 20 minutes to Key West!! We would stay there again.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Grand Blue Arenas/ 120'Dock/Mini golf/GameRoom

GinaRating, 5 stars1 week ago
We had an absolutely amazing stay at this beautiful home in Marathon Keys! From the moment we arrived, it was clear that this property is extremely well-maintained and spotless. The house was immaculately clean, which made settling in with kids feel effortless and comfortable.The two-story layout was perfect for our family, offering plenty of space for everyone to spread out and relax. The home is definitely kid-friendly and family-oriented, with thoughtful touches throughout. The pool was a huge hit with both the kids and adults, and we had so much fun spending our evenings enjoying it! The kitchen was gorgeous and fully equipped with high-quality appliances, which made cooking meals together easy and enjoyable. We brought both a 22-foot bay boat and a 22-foot pontoon, and docking was a breeze. Overall, this home was the perfect place for our family getaway. We made unforgettable memories here and would absolutely return. Highly recommended for families looking for a home in the Keys!

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 stars4 weeks 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
4.89 out of 5 average rating, 142 reviews

Tropical Escape at Sunrise

MalloryRating, 5 stars1 month ago
We enjoyed our stay! A little outside of the heart of Key West so it was very quiet. This place does have a unit above, luckily we were not bothered by any sort of upstairs noise. Would recommend!
Superhost
Apartment in Key West
4.85 out of 5 average rating, 156 reviews

Anchor Drop modern elegance upgrades throughout vi

MoiraRating, 5 stars6 days ago
This was a great condo for 5 of us! PROs- Everything was so nice and clean. The owners are super organized with labeling on sheets, pillows, games, pool toys, etc all clearly marked in bins. The kitchen was well equipped, even though we didn't use it much. The sitting area around the TV was perfect and plenty of room for everyone. The master shower is huge and the bathrooms were very clean. We loved the large balcony. The pool was so nice and plenty of room and chairs, very well maintained. Communication with the property management company was pretty good, although it was more than 12 hours response time on one of the questions we had. They were very helpful and available on a Friday night when we were trying to access the TV and had questions on how to connect, which was great since it was a weekend. CONS- the condo is not situated very close to the Old Town area or restaurants. We took ubers and had a car, so it didn't really bother us. I would definitely book this place again!
Guest favourite
Apartment in Key West
4.89 out of 5 average rating, 168 reviews

A Perfect Getaway

DavidRating, 5 stars3 weeks ago
We had a wonderful visit in Key west. The place was very clean, close to everything. We enjoyed this place very much and would rent it again. Thank you so very much. Sue and Dave Hopper.
Guest favourite
Apartment in Key West
4.9 out of 5 average rating, 211 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

AlexRating, 5 stars1 week ago
Jennifer’s place was exactly what we were looking for, it was a quiet corner unit with lots of space for four guests, a large kitchen (we love to cook elaborate meals even when we travel and we had everything we needed here), great views of the harbor, was squeaky clean, and ample parking. Jennifer communicated everything we needed to know well ahead of time and promptly replied to any questions we had. Would absolutely stay here again!
Top guest favourite
Apartment in Marathon
4.96 out of 5 average rating, 104 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

PaulRating, 5 stars2 weeks ago
Host was extremely helpful and communicative. Check in was a breeze and all the amenities needed for a pleasurable stay. Bonus outdoor bait freezer!
Superhost
Apartment in Marathon
4.85 out of 5 average rating, 239 reviews

Sombrero Beach Tropical Getaway

JoseRating, 5 starstoday
The room was very clean and tidy and perfectly cooled temperature. All amenities worked and were very clean. Enjoyed the security of the place. We enjoyed the stay & will book again for later trips to the area. Very recommended! Thanks Phil!
Guest favourite
Apartment in Key Colony Beach
4.81 out of 5 average rating, 138 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

RandyRating, 5 stars1 week ago
The place was exactly as described the only complaint I have is the bed is firm but it didn’t bother my wife at all . The rainfall shower head was a 10/10 after a long day in the heat ! The onsite grills were awesome we grilled 2 of our 4 nights since it was so convenient.

Quick stats about holiday rentals with a pool in Summerland Key

  • Total rentals

    200 properties

  • Nightly prices starting at

    ₹3,462 before taxes and fees

  • Total number of reviews

    4.1K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

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