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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
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, 166 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
Home in Goulds
4.95 out of 5 average rating, 112 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 favourite
Home in Miami
4.94 out of 5 average rating, 225 reviews

Miami Getaway - Heated Pool, Hot tub, BBQ

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.

Guest favourite
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
4.95 out of 5 average rating, 110 reviews

Family Oasis Retreat• 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 favourite
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
4.88 out of 5 average rating, 186 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

Superhost
Villa in Miami
4.9 out of 5 average rating, 155 reviews

One Of A Kind Smart Villa - Pool/Spa/Gym/BBQ/Vibes

🎨 House of Art Miami — where design becomes the experience 🎨 This art-forward smart villa blends resort-style amenities with the comfort, privacy, and freedom of a home. Designed for groups to relax, connect, and enjoy Miami together — without feeling rushed or crowded. 🔥 Heated pool, jacuzzi, fire pit & BBQ 🏀 Mini golf, ping pong & basketball 🖼️ Curated art + immersive sound indoors & out 📍 Minutes from beaches, dining & nightlife More than a stay. An experience. @BeyondTheBNB

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
4.97 out of 5 average rating, 271 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.

Superhost
Home in Cutler Bay
4.86 out of 5 average rating, 154 reviews

South Miami Gem • Near Zoo Miami, The Falls | Pool

Discover the pinnacle of modern living in this newly remodeled 7-bedroom, 4-bath masterpiece. With sleek architecture and designer touches, this South Miami retreat offers a private heated pool and resort-style amenities for a truly unforgettable stay. Perfectly situated near stunning beaches, the Miami Zoo, Southland Mall, and top attractions, it’s your gateway to the best of South Florida. Experience unmatched comfort and sophistication—this one-of-a-kind home awaits you!

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 Kendall
4.97 out of 5 average rating, 405 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 favourite
Home in Miami
4.93 out of 5 average rating, 157 reviews

Private Miami Retreat/Htd Pool + Outdoor Kitchen

Private tropical retreat in Miami. 4BR · 2BA · sleeps 8. Heated pool, fire pit lounge, fully equipped outdoor kitchen & covered terrace. Master bath with spa rainfall shower. Surround sound indoors & outdoors. Stainless kitchen with pool views. Family-ready: crib, playpen, highchair, infant car seat & safety gate. Free parking · Fast WiFi · Self check-in. Superhost 4.93★ · 155 reviews. Quiet neighborhood.

Superhost
Home in Cutler Bay
4.87 out of 5 average rating, 220 reviews

Relax Oasis • Near Zoo Miami | Pool_Spa•BBQ•Court

Heated pool/Jacuzzi/Basketball court/5B 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.

Guest favourite
An inviting pool area features clear blue water surrounded by a privacy fence and lush greenery. Sunlight reflects off the pool’s surface, creating a serene outdoor space ideal for relaxation and enjoyment.
Home in Princeton
4.87 out of 5 average rating, 116 reviews

Tropical Paradise Between Miami and the FL Keys

Located within a quiet and desirable neighborhood is this stunning ultra-modern home offering unparalleled style and design across 2 levels of luxury living. The house features a living room, a kitchen, 3 luxurious bedrooms, an incredible games room and glamorous outdoor living with a swimming pool and outdoor dining and an incredible children's play place.

Popular amenities for Cutler Bay rentals with a pool

When is the best time to visit Cutler Bay?

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Avg. price$292 SGD$285 SGD$339 SGD$301 SGD$306 SGD$327 SGD$340 SGD$330 SGD$303 SGD$310 SGD$339 SGD$399 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 $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,120 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

  • 4.7 Average rating

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