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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
4.95 out of 5 average rating, 161 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.

Guest favorite
A wraparound balcony offers panoramic views of Biscayne Bay and the Miami skyline. The scenic vista is complemented by lush greenery below and various buildings in the foreground. The sky is bright with scattered clouds, enhancing the sense of openness and tranquility.
Apartment in Coconut Grove
4.9 out of 5 average rating, 223 reviews

Stunning Studio w/Bay & City View Free Park/Pool

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! in Coconut Grove, this privately owned & renovated deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

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, 191 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!

Guest favorite
Home in Goulds
4.94 out of 5 average rating, 106 reviews

Cozy house

Welcome to Your Tranquil Getaway! Discover a serene escape at our unique and tranquil retreat, perfect for families and friends seeking relaxation and adventure. This beautifully designed property features a sparkling private pool, ideal for enjoying sunny days and creating lasting memories. Nestled in a prime location, you’re just minutes away from top attractions such as Monkey Jungle, the Miami Metro Zoo, Black Point Marina, and the Florida Keys. Explore nearby gems like Gilbert’s Resort.

Guest favorite
The outdoor area features a heated pool surrounded by colorful murals, with a jacuzzi nearby. Poolside loungers and a basketball hoop are visible, offering a vibrant space for relaxation and fun under a clear blue sky.
Home in Miami
4.97 out of 5 average rating, 106 reviews

Family retreat oasis, heated pool, jacuzzi & grill

Welcome to Forget-me-not Villa, a sanctuary for your family and friends to let loose barefoot and unwind in the private backyard fully fenced, feel the breeze, stargaze at night, and savor the comfort of our exquisite vacation home. The villa features a heated pool and jacuzzi, a grill station, a love seat for romantic moments, a playground for children, an Xbox S for gamers, board games, mini golf, pool volleyball and basketball hoop, Smart TVs& high-speed Wi-Fi & electric car connection.

Guest favorite
An outdoor patio area features comfortable seating arrangements under a shaded pergola, overlooking a large swimming pool. The vibrant green lawn is bordered by palm trees, while the sunset colors softly illuminate the sky in the background.
Villa in Miami
4.89 out of 5 average rating, 181 reviews

NEW! "Villa Paradise" ~ Luxury Gem ~ Pool ~ Game Room

Bring your family to the luxurious 3BR 2Bath Villa Paradise in the tranquil and friendly neighborhood in southern Miami, FL. Visit the exciting attractions, natural landmarks, restaurants, shops, and much more, and then retreat to the lavish oasis that will leave you in awe with its stylish design, private backyard, and rich amenity list. ✔ 3 Comfortable BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Heated Pool ✔ Game Room ✔ Smart TVs ✔ Smart House ✔ High-Speed Wi-Fi ✔ Free Parking

Top guest favorite
The entrance of the property is framed by mature palm trees and lush landscaping, showcasing vibrant greenery. A large half-circle driveway leads up to the house, highlighted by a smooth, paved surface. The warm-toned exterior of the home is visible, inviting guests into a tranquil setting.
Guest suite in Miami
4.91 out of 5 average rating, 433 reviews

Cozy Suite -Exterior Entrance, SelfCheckin

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Room 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 -Bathroom with 2 sinks -SWIMMING POOL -Central A/C -HBO TV -Refrigerator -Ceiling Fan -Closet Space -Ceramic Tile Floors -Iron & Board -Towels & Bath essentials -Hair dryer

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, 307 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.

Guest favorite
A serene outdoor space includes a swimming pool surrounded by terracotta tiles and lush tropical vegetation. A tiki hut is positioned in the background, with an evening sky showcasing warm tones of orange and yellow. Soft furnishings and a relaxed seating area are visible nearby.
Tiny home in Cutler Bay
4.97 out of 5 average rating, 266 reviews

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. Enjoy the miles of nearby walking paths stretching from Coconut Grove to Black Point Marina.

Top guest favorite
Condo in Coconut Grove
4.99 out of 5 average rating, 134 reviews

Your Bay View Escape in Coconut Grove, Pool & Gym

- Enjoy breathtaking bay views & sunsets in this fully remodeled Coconut Grove condo - Private balcony perfect for relaxing and taking in the scenic surroundings - Full access to building amenities, including a gym, pool, sauna/steam room and jacuzzi -Onsite restaurant, valet/parking and 24/7 security. - Located just steps from Coconut Grove’s best restaurants, shops, and marinas -Fully equipped kitchen, luxurious oversized shower and cozy bedroom with work desk.

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, 398 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.

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, 863 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.

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.ﺇ892ﺩ.ﺇ977ﺩ.ﺇ1,149
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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 3,120 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

  • 4.7 Average rating

    Cutler Bay stays receive an average rating of 4.7 out of 5 from guests