
Holiday rentals with a pool in Cutler Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cutler Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Cutler Bay rentals with a pool
House rentals with a pool

Kendall Keys Oasis w/ HEATED Pool Theater & Arcade
I LOVED LOVED LOVED Christopher's house!! It was beautiful! I honestly felt like i never left my house it was so cozy. Also it wasn't to far from everything we wanted to do. When i had a question to ask he responded quickly and i appreciate that. Thank you so much for sharing your lovely home with us. I definitely will be staying there again.

Family retreat oasis, heated pool, jacuzzi & grill
this Airbnb was perfecttt, the aesthetics of the home was beautiful And the host was very accommodating and responsive . Definitely recommend this Airbnb if in the Miami area.

Luxurious & Comfy Family Gem ~ Sunny Pool ~ Games!
Juan was a phenomenal host he replied right away and when we had a minor issue he addressed it right away. A beautiful home in a great neighborhood Juan is a Very very nice guy. He was responsive to a special request I made and was very clear about his expectations . All around a fantastic experience. It is a Lovely spacious home We stayed at another property a year ago for about the same amount of money and the same guests and it was the polar opposite from this stay . The A/C was non functional it was hotter inside than outside (7th layer of hell) Found out later that it had been non functional for months . It was dirty ,we do not wear shoes inside and our on feet were black. It smelled stale and the sofa was beer soaked ( hope it was just beer ) oh yes it had a broken large picture window facing the lake in the rear of the house . There was glass all inside the sunroom. We cleaned it up. But with no screen mosquitos came in. So this stay was especially great.

South Miami Gem!
Highly recommended! The place was clean and cozy, community was great.

Charming house with private pool & large patio
This place looked better in person. Than what’s on the website…… My family and I adored this home …. The host and his wife really out did my expectations. I’m coming back to Miami in October, my two sisters and I and I hope that I’m welcomed back . 🙏🏾🙏🏾🙏🏾🙏🏾🙏🏾

Resort Style Pool House Mini-Golf Game-Room Casino
Great location for the price, lots of fun amenities. Would definitely stay here again if going to Miami or Key Largo.

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ
Was looking for a getaway and found Jessica and Javier’s home so I decided to give it a try. I was NOT disappointed. It is a beautiful home from the moment you walk in, to the backyard with an amazing pool to relax in. The house was very clean and smelled very clean/good. Parking was great and the overall experience was awesome. I would definitely be back. They were great hosts! :) If you’re thinking about booking, do it.. you will not regret it!

BellaMoon Oasis Miami
Staying at this home in Miami was hands down the best decision we made. The house is spotless, spacious, super comfortable, and fully equipped with everything you could possibly need. Every detail is thoughtfully taken care of, and that made all the difference in our stay. Now, let’s talk about Glen – what an amazing host! From the very beginning, she was incredibly helpful, kind, and always available for anything we needed. She truly cares about her guests, and you can feel it in every interaction. Glen went above and beyond to make sure everything was perfect for us – and it truly was! We 100% recommend this place. There’s no better option in Miami! If you’re looking for a beautiful, welcoming home with a fantastic host, this is it. Thank you so much, Glen – we’ll definitely be back!
Apartment rentals with a pool

Feels Like Summer ~ Panoramic Water Views! 2BR
Wow! What a fabulous apartment! We had the most amazing stay to celebrate my birthday! This apartment had everything we needed, a home from home! Immaculate throughout and in such a central location with AMAZING views!! These hosts were fantastic! Thank you so much! If you’re looking to stay in Miami, this is the one to book!

Chic Studio 5 Icon Brickell Amazing View
The place was beautiful looked even better than the photos, the bed was super comfortable, view was extremely beautiful, only problem was I wish it was more towels I asked for them but nobody ever brought them. Other than that everything was great, also be prepared to pay at least $40-50 a day for parking. Great host he was there right away to help with check in and gave us a better rate for parking which was $40 a day.

Miami Design District Luxury Unit Stunning Views
Nice unit with just enough space. nice view and amenities. Design district has,a lot to do and location makes Miami easy to navigate and get around. Well priced.

Key Biscayne little beach place
Fantastic location very close to beach. Very cozy condo. Well kept. Upgraded bathroom and kitchen.

Modern DT Studio | Near Port Miami + Free Parking
Host was super helpful and communicative. Apartment was accurately described by the photos. Washer and dryer a huge plus! Convent location and great amenities. Would recommend.

Upper Penthouse Corner Unit 2B/2B | Icon Brickell
My 2 daughters and I had a wonderful stay at Alican Penthouse. The place was spotless, tastefully decorated, and had all the essentials. The view from the balcony was breathtaking, especially at night. It was a peaceful escape with restaurants, spas, gyms, hot and cold pools on site but still just a 10-minute drive from the restaurants , beaches, clubs, shops and malls. Looking forward to another visit.

Luxury Miami Studio 3013 View, Pool, Gym Amenities
While in my stay in the condominium it was nothing short of the photos on the listing. It was clean, well organized, and to top it all off has a great ocean view and of downtown Miami. Has many walkable locations and restaurants in the area as well. Also has great amenities like a gym, pool, and restaurant in the lobby. Would for sure stay here again and recommend it to others as well.

Beautiful Blue & Gold Studio with Ocean View
The efficiency was really nice. Gorgeous view, comfortable and clean. Being a native Miamian and born and raised in the Grove, it was refreshing to know that everything was right at reach. I would book again
Quick stats about holiday rentals with a pool in Cutler Bay
Total rentals
60 properties
Nightly prices starting at
$52 SGD 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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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Miami Beach Convention Center
- Haulover Beach
- Everglades National Park
- Hard Rock Stadium
- Bal Harbour Beach
- Miami Design District
- Port Everglades
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Ocean Terrace Public Beach
- Trump National Doral Miami
- Crandon Beach
- Phillip and Patricia Frost Museum of Science
- Dania Beach
- Key Biscayne Beach
- Coral Castle
- Hobie Island Beach Park North
- Jungle Island
- Cannon Beach
- Biltmore Golf Course Miami
- Fairchild Tropical Botanic Garden