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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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Guest favourite
The living area features a spacious blue tufted sofa complemented by a sleek glass coffee table. A modern accent chair adds contrast, while large sliding glass doors provide ample natural light and stunning views of the surrounding skyline.
Apartment in Downtown Miami
4.92 out of 5 average rating, 119 reviews

Make It Happen! Brand New with Amazing Water Views

Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Make It Happen! is the ultimate retreat, equipped with everything you could need. Enjoy views of Biscayne Bay and Margaret Pace Park that will leave you in awe. With South Miami Beach 3 miles away you can indulge in the sun of Miami Beach while still feeling the energy of downtown Miami, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

Guest favourite
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, 148 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 favourite
The treehouse stands surrounded by lush greenery and vibrant flowers. A set of stairs leads up to the entrance, which is framed by tropical plants. Decorative stones and a pathway enhance the serene garden setting, creating a tranquil environment.
Tiny home in Cutler Bay
4.93 out of 5 average rating, 131 reviews

Cozy Treehouse in Private Garden, Pool

Read entire listing for FAQ Contact AIRBNB for changes to your reservation We welcome all! Come reconnect with yourself and nature in this Zen garden. Surrounded by love, peace, nature in peaceful surroundings Located between Miami Beach & The Keys Beautiful & Quiet Residential Area South of Miami Close to all major roads. *this is a treehouse, so it is a small space, FULL SIZE bed (54 x 75 inches). Private bathroom adjacent to treehouse. Look at our other listings in main house.

Top guest favourite
The exterior of a private guesthouse is showcased, surrounded by lush greenery and tropical plants. Screened windows provide a view of the outdoors while offering a sense of openness. The building is designed with a light-colored façade, blending harmoniously with the natural setting.
Guest house in Miami
4.97 out of 5 average rating, 204 reviews

Cozy private guest studio

Welcome! This is a private guesthouse located in a quiet neighborhood. Accommodations are with a private entrance and parking space to make you feel at home. We are located near a major expressway. We have a pool; The POOL is a SWIM AT YOUR OWN RISK. It is shared with Owner. Enjoy a smoke free cottage. Ashtrays are provided outside for those guest that do smoke. We provide a queen size bed and a couch/bed. This space is perfect and comfortable for two guest.Please NO children and NO animals.

Top guest favourite
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
4.98 out of 5 average rating, 252 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. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Top guest favourite
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.
Flat in Miami
4.94 out of 5 average rating, 184 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 favourite
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, 381 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

Top guest favourite
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, 419 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

Top guest favourite
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, 392 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 favourite
A fire pit is positioned on a stone patio, featuring a modern design with blue glass accents and flickering flames. In the background, a heated pool is surrounded by lush greenery and comfortable outdoor seating, providing an inviting space for relaxation.
Home in Miami
4.92 out of 5 average rating, 145 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.

Superhost
A heated pool surrounded by lounge chairs and a colorful float can be seen. The pool area features bright blue water under a clear sky, with palm trees in the background. A textured patio provides space for relaxation and enjoyment.
Home in Cutler Bay
4.87 out of 5 average rating, 209 reviews

Miami Oasis: Heated Pool, Spa & Basketball

Heated pool/Jacuzzi/Basketball court/5BR Indulge in luxury for a relaxing vacation, basking in Miami's warm weather. Revel in our spacious heated pool and Jacuzzi adorned with umbrellas, loungers, and snack tables. Each room is tastefully decorated with meticulous care. Sports enthusiasts will adore our basketball court. Perfect for your family and friends, our space awaits.

Top guest favourite
Home in Miami
4.96 out of 5 average rating, 113 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?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$298 SGD$291 SGD$346 SGD$307 SGD$312 SGD$334 SGD$347 SGD$337 SGD$310 SGD$264 SGD$278 SGD$295 SGD
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Quick stats about holiday rentals with a pool in Cutler Bay

  • Total holiday rentals

    Explore 60 holiday rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,500 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Cutler Bay holiday rentals include wifi 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!