Vacation rentals with a pool in Cutler Bay

Find and book unique homes with a pool on Airbnb

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Popular amenities for Cutler Bay rentals with a pool

House rentals with a pool

Guest favorite
Home in Hollywood
4.94 out of 5 average rating, 148 reviews

LUXURIOUS SUPER HOST HOLLYWOOD HOUSE, POOL HEATER

StephanieRating, 5 stars1 day ago
Stay was perfect. Had issues with Tesla charger and she had someone on site within an hour fixing and troubleshooting the issue, fixing it and going above and beyond with any help, questions, concerns etc. I stayed with my family and although the pool is not gated the house itself had perfect child lock on the back door to prevent any accidents etc. kids loved the PS5 and arcade machine. Pool is warm and perfect to cool off, grill and entertainment like pool table, ping pong table etc kept everyone entertained.
Guest favorite
Home in North Miami
4.95 out of 5 average rating, 156 reviews

Bright and fun saltwater POOL home - 5 bedrooms

DesmondRating, 5 stars2 days ago
We had a great stay! The house was very clean, the pool was a nice, and the location was perfect close to everything we needed. Would definitely recommend to others and stay again!
Top guest favorite
Home in Coral Way
4.95 out of 5 average rating, 148 reviews

Modern 4BR/4B - Monthly Rental - Summer Sale

ErinRating, 5 stars3 weeks ago
I would give six stars if i could! What a wonderful experience. Location is was great, house was spectacular, host was such a wonderful communicator!
Guest favorite
Home in Hollywood
4.92 out of 5 average rating, 163 reviews

Hard Rock Villa - House With Pool & Selfie Walls

ThomasRating, 5 stars2 weeks ago
Had a great time location was perfect and pool was a nice touch. Very spacious and private super close to the casino
Superhost
Home in Allapattah
4.86 out of 5 average rating, 156 reviews

Urban Oasis With Pool at West Wynwood/Allapattah

AndrewRating, 5 stars1 week ago
Good value for what we paid and had all the amenities we needed! Close to the airport and within walking distance to McDonald's as well. Note that shampoo/body wash are not provided in the bathrooms. Host was proactive and easily reachable.
Guest favorite
Home in Miami
4.86 out of 5 average rating, 169 reviews

6-BR Vacation Home for Bachelorettes & families

MatthewRating, 5 stars2 weeks ago
This house was Wonderful, I booked for my Wife’s birthday and everything was PERFECT. Our host was very accommodating and responsive, the overall experience was just fantastic.
Superhost
Home in Rio Vista
4.83 out of 5 average rating, 162 reviews

Large Waterfront House with Pool 4bd/2ba

YolandaRating, 5 stars1 week ago
We had a perfect family getaway right here in Las Olas! The place was super clean, cozy, and just minutes from the beach, shops, and restaurants. Loved the relaxing vibe , it felt like a mini staycation with all the perks. Host was responsive and made everything easy. Definitely recommend for anyone looking for a escape! 🏖️🌴
Guest favorite
Home in Fort Lauderdale
4.95 out of 5 average rating, 186 reviews

Downtown Ft Lauderdale 3 bedroom HEATED Pool Home

AnnaRating, 5 stars1 week ago
Host was very responsive and accommodating! Allowed us to check-in a little early, everything was very clean, kitchen had plenty of items for us to cook with, beach towels, board games, etc. definitely would stay here again 😇

Condo rentals with a pool

Guest favorite
Condo in Brickell Business District
4.9 out of 5 average rating, 206 reviews

Luxury Deal!40th Floor*Miami*Sleeps9*RENOVATED!

PreedmanRating, 5 stars1 week ago
Excellent accommodation with stunning balcony views. The space was clean and spacious. Although we didn't plan to use the building much, the pool and gym amenities were a great addition. We particularly enjoyed the pool.
Guest favorite
Condo in Sunny Isles Beach
4.89 out of 5 average rating, 104 reviews

Luxury Beach & City View Condo 5 min walk to beach

GlenRating, 5 stars4 days ago
This place is very clean. Host was very responsive and helpful for any questions of my needs. Beautiful location and the pictures match 1000%. Thanks again Joe and Cindy. Next time I’m In the area will be staying here again.
Guest favorite
Condo in Sunny Isles Beach
4.88 out of 5 average rating, 107 reviews

Golden Bay Club Beautiful Condo! -STR-02901.

JimRating, 5 stars1 month ago
The apartment is exactly as described. This is a tremendous place to relax, recover and enjoy the sunny isles of Florida. Fernando and team were incredibly gracious and responsive. Would definitely stay there again (hopefully very soon)
Superhost
Condo in Hollywood Beach
4.83 out of 5 average rating, 36 reviews

Luxurious 3/3 Resort Condo by the Beach

WinfieldRating, 5 stars7 months ago
Anthony has a great property in a prime location. The view is amazing. Friendly and responsive host. We would stay here again!
Guest favorite
Condo in Miami
4.9 out of 5 average rating, 21 reviews

Modern Spacious 2 Bed In Aventura/ FREE Parking

RekuckiRating, 5 stars2 months ago
Fully equipped, nicely decorated, clean and spacious apartment in good location . Thank you Dmitry!
Superhost
Condo in Miami Design District
4.69 out of 5 average rating, 36 reviews

Modern 1BR +Free Parking Pool Gym @Miami Design

PumRating, 5 stars7 months ago
The best a vacation Airbnb so far in my life
Top guest favorite
Condo in Sunny Isles Beach
5 out of 5 average rating, 30 reviews

Oceanfront Remodeled Beautiful Condo

UljanaRating, 5 stars2 months ago
We had a wonderful stay at this condo! The space was clean, well-maintained, and had everything we needed for a comfortable stay. The beautiful ocean view from the spacious balcony was a highlight, and the location couldn't have been better - perfect for easy access to everything nearby. The owner was incredibly helpful and made sure we had all the information we needed. Highly recommend this place for anyone looking for a relaxing getaway!
Guest favorite
Condo in Sunny Isles Beach
4.87 out of 5 average rating, 63 reviews

Beautiful modern 2 bedroom condo across the beach.

ShamaraRating, 5 stars2 weeks ago
Daniel’s place was exactly as pictured—clean, comfortable, and very relaxing. I had a beautiful view of the pool, and the ocean was just a short walk away. There was also a supermarket nearby, which made everything super convenient. The check-in process was smooth and simple, and Daniel was very responsive throughout my stay. I really appreciated the little touches—like the beach chairs he provided. I was able to carry one on my back and walk to the beach instead of paying $10 to rent one. That made a big difference and really added to the experience. I also used the barbecue area and ended up meeting some great people while grilling—such a fun bonus. Overall, I had a wonderful time and would definitely stay here again. Highly recommend!

Quick stats about vacation rentals with a pool in Cutler Bay

  • Total rentals

    60 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    3.5K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

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