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Vacation 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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Guest favorite
A refreshing outdoor pool is framed by palm trees and a surrounding patio of laid stones. Two loungers are positioned partially submerged in the water, complemented by a large umbrella for shade. The clear sky is visible above.
Home in Cutler Bay
4.96 out of 5 average rating, 156 reviews

King Bed Home by the Bay FAST WI-FI & Coffee

Whether you are visiting the Florida Keys, the beaches of Miami, or looking for a comfortable staycation, discover what South Florida has to offer while feeling at home. You'll be located near Southland Mall, The Falls Shopping Center, Black Point Marina, Miami Metro Zoo, Deering Estates, the Dennis C. Moss Arts Center and more! ❧ 48 minutes from the Florida Keys. ❧ 37 minutes from Miami Beach. ❧ 33 minutes from the Everglades. Message us about long stay, military, & first responder discounts.

Top guest favorite
The outdoor pool area features a clear blue salt-water pool, surrounded by lounge chairs and shaded by umbrella canopies. A natural rock slide is integrated into the design, set against lush green foliage and palm trees in the background.
Apartment in Miami
4.94 out of 5 average rating, 188 reviews

Very Private 1/1 Apt w/Oasis Pool Patio Setting

Private apartment-1 bedroom w/king size bed, 1 full size bathroom, separate living and dining area. Fully equipped kitchen. Free parking, beautiful oasis setting with salt water pool, hot tub & patio. Gazebo w/fire pit, Bar-be-cue, 2 TV’s, free WiFi. This is NOT a party spot but a place to relax in the pool, hot tub or relaxing dinners at home after visiting Miami venues. Set in a quiet neighborhood, 2 miles from shopping & restaurants. This is your home away from home vacation spot!

Top guest favorite
A spacious driveway curves past vibrant tropical plants and palm trees leading to a welcoming entrance of the property. The house features a warm orange exterior with decorative elements and a large garage door, complementing the lush landscaping.
Guest suite in Miami
4.9 out of 5 average rating, 384 reviews

Guest Suite-Exterior Entrance, SelfCheckin.

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel safe and welcome here! -GATEWAY to the Keys and Everglades -Private entrance -Self Check-in -Free Parking -Fast WIFI -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

Guest favorite
Home in Miami
4.94 out of 5 average rating, 213 reviews

Miami Getaway - Heated Pool, BBQ, Washer & Dryer

Be our guest and have a wonderful stay in this beautiful Miami home designed to create great memories. 3 bedrooms 2 bathrooms with enough space to sleep 10 guests. Heated pool & seperate HotTub to enjoy even during winter season. Conveniently located within a short distance from all of Miami's main attractions. Restaurants, shopping malls, nightclubs, bar/pubs, art centers, bicycle trails, beautiful parks and bay views between 5 - 10 minutes away. Only 50 minutes away from the Florida keys.

Top guest favorite
A spacious backyard is showcased, featuring a clean saltwater pool surrounded by lounge chairs and tropical landscaping. A covered patio area is visible, with a stone countertop and decorative plants. The bright blue sky complements the serene outdoor setting.
Home in Miami
4.99 out of 5 average rating, 395 reviews

Sanctuary Salt water heated pool BBQ Grill Oasis

Come and create unforgettable memories in this modernly designed single-family home with a spacious layout and a range of comfortable bedrooms. It features two king-size beds, one queen-size bed, and a twin fold-up bed, as well as an Italian queen-size sofa bed. The house is bathed in natural light and boasts modern amenities that cater to your convenience. Located in a prime location, this house is close to all the tourist areas!! The pool is salt water with heater, Also a grill area

Guest favorite
A spacious lawn features a large shade tree with swings hanging from its branches. Nearby are colorful chairs arranged on the grass, along with a hammock tied between tree trunks. Water is visible in the background, surrounded by lush greenery.
Guest suite in Cutler Bay
4.78 out of 5 average rating, 303 reviews

Private Waterfront Studio Paradise

Casa Cocos is a private studio, with a private entrance, bathroom and kitchenette, and free and secure parking. It is nestled in Florida's tropical waterfront paradise. Come enjoy the views of the garden, go for a swim, paddle board, canoe, kayak, grill, take a nap in a hammock, and just relax. Casa Cocos is surrounded by nearby restaurants, bars, retail stores, malls all within walking distance or a short drive. 30 minutes to airport, downtown, South Beach, Keys, and Everglades.

Top guest favorite
A spacious pool area is surrounded by vibrant greenery and palm trees. Seating arrangements with cushions are positioned near the water, complemented by a shaded area under an umbrella. The pool features a rock formation and is accented by colorful lounge chairs.
Home in Miami
4.97 out of 5 average rating, 396 reviews

The Miracle Cottage & Pool on Acre Miami Florida

Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

Top guest favorite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
5 out of 5 average rating, 164 reviews

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Guest favorite
A serene waterfront view showcases several three-story buildings framed by palm trees. The calm water reflects the bright blue sky dotted with fluffy clouds, while a fountain creates gentle ripples, enhancing the tranquil atmosphere of the resort.
Condo in Miami
4.95 out of 5 average rating, 831 reviews

Marriott Villas and Doral 2BD sleeps 8

Located in one of the most prestigious areas of Miami, Marriott's Villas at Doral are a tranquil hideaway; only 13 miles from the sizzling excitement of Miami Beach, yet a world away. Sharing the 650-acre lush landscape is the celebrated Trump National Doral Miami, a Trump-managed resort. There, you have access to four championship courses, a classic European spa, a water recreation playground and several restaurants.

Guest favorite
Home in Miami
4.93 out of 5 average rating, 149 reviews

Poolside Haven 4/2, Htd pool, oudr ktch by freeway

2 King beds, 1 queen bd, 2 double beds, 2 bath, heated pool, outdoor kitchen, self check in, fire pit Free private parking, fast wifi. Surround sound systems indoors and outdoors. Master bath with spa-style rainfall shower. Fully equipped kitchen with stainless steel appliances. Family-friendly: crib, playpen, highchair, infant car seat, safety gate. Quiet, established neighborhood.

Top guest favorite
A clear blue pool is framed by a protective screen enclosure, creating a serene swimming environment. Lush greenery surrounds the pool area, and a guesthouse is visible in the background, featuring a simple facade with a centrally located door.
Guesthouse in Homestead
4.97 out of 5 average rating, 182 reviews

Charming Private Pool house for two.

Charming private back pool house on a fenced property in a quiet neighborhood close to US 1, the Turnpike, the Keys, Nascar and the Homestead Speedway, and the Everglades. You are 15-20 minutes from the Speedway, 20 minutes from the Everglades, and 30 minutes from Key Largo. For guests wishing to stay a month or more, I would require you to provide a copy of your photo ID.

Top guest favorite
Home in Miami
4.96 out of 5 average rating, 117 reviews

Miami Lux Lake Front Retreat

A destination on its own: 1. Spacious home- over 5500 sqft of living space. 2. Gym with sauna and steam shower. 3. Pool table 4. Gourmet kitchen. 5. Formal dining room. 6. Large TV room with leather sectional, all recliner. 7. Karaoke 8. Kayaks to enjoy the lake 9. Heated Pool 10. Outdoor ping pong 🏓 table 11. Gym 12. Sauna and steam Room

Popular amenities for Cutler Bay rentals with a pool

When is the best time to visit Cutler Bay?

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Avg. priceﺩ.ﺇ841ﺩ.ﺇ823ﺩ.ﺇ977ﺩ.ﺇ867ﺩ.ﺇ881ﺩ.ﺇ944ﺩ.ﺇ981ﺩ.ﺇ951ﺩ.ﺇ874ﺩ.ﺇ746ﺩ.ﺇ786ﺩ.ﺇ834
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Quick stats about vacation rentals with a pool in Cutler Bay

  • Total vacation rentals

    Explore 60 vacation rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 3,500 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Cutler Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cutler Bay rentals

  • 4.8 Average rating

    Cutler Bay stays are highly rated by guests—averaging 4.8 out of 5!