Some info has been automatically translated. Show original language

Vacation rentals with a pool in Cutler Bay

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Cutler Bay

  • Total vacation rentals

    Explore 50 vacation rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay vacation rentals start at G$10,442 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,340 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 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!

Top-rated rentals with a pool in Cutler Bay

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
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, 170 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
Home in Miami
4.94 out of 5 average rating, 234 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.

Superhost
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
4.86 out of 5 average rating, 195 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
Home in Miami
4.98 out of 5 average rating, 103 reviews

Oasis & Art / Artificial Beach / Heated Pool / Mini Golf

House in Miami, Sleeps 12 Heated Pool/Mini Golf/Kids Playground/BBQ/Cornhole game/Small beach/mini football Ned/Hammocks. Peace, nature, fun and more you will find in our house. The house is decorated with unique original art. Don't miss out on this newly remodeled cozy home, an ideal retreat for a peaceful and rejuvenating vacation. With a spacious living room, dining area, and a fully equipped kitchen, this house has everything you need. Nestled in a secure and tranquil neighborhood.

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, 313 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 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
4.96 out of 5 average rating, 282 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.

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
4.93 out of 5 average rating, 123 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.

Top guest favorite
Apartment in Downtown Miami
4.89 out of 5 average rating, 461 reviews

Biscayne Bay Studio: Resort Pool & Beach Access

Guest verdict: "A perfect apartment, super responsive hosts, 1000% clean, and amazing amenities and location. We might not ever stay in Miami Beach proper ever again!" This modern studio features a gorgeous view overlooking Downtown Miami & Biscayne Bay. Just steps from Bayfront Park and a 4-minute walk to Bayside Marketplace, its great location provides immediate access to attractions. Ideal for April travelers seeking convenience and a vibrant Miami experience.

Superhost
A screened-in pool area showcases a large pool and an attached hot tub. Lounge chairs are positioned around the pool, while a dining table with chairs is visible nearby. Lush greenery surrounds the space, creating a tranquil outdoor atmosphere.
Home in Cutler Bay
4.77 out of 5 average rating, 145 reviews

Heated Pool/Jacuzzi Paradise: Cozy Miami Retreat

Welcome to our spacious 3 bedroom, 2 bathroom home located in the highly desirable Cutler Bay neighborhood! The home is perfect for families, couples, or friends looking for a comfortable getaway. Our home boasts a large pool with an attached Jacuzzi and a screened-in pool area perfect for enjoying the Florida sun. ✔ Fully Equipped Kitchen ✔ Comfortable Bedrooms with King/Queen/Full beds ✔ Open Concept Living Area ✔ Office Desk ✔ Piano ✔ High-Speed Wi-Fi

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 Kendall
4.97 out of 5 average rating, 419 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, 211 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
Home in Miami
4.89 out of 5 average rating, 114 reviews

Modern 5BR Oasis • Pool & BBQ | Near Redland & Zoo

Escape to your private tropical oasis in Miami. Enjoy a private pool, mini golf, BBQ nights under a tropical pergola, and hours of fun with billiards & ping pong. Start your stay with a complimentary welcome bottle of wine and the ease of self check-in. Located in a quiet central area, close to South Beach, the Florida Keys, and Miami Zoo. Perfect for families, couples, business trips, or groups seeking comfort, fun & privacy.

Popular amenities for Cutler Bay rentals with a pool

When is the best time to visit Cutler Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$55,552 GYDG$52,628 GYDG$60,355 GYDG$49,287 GYDG$50,122 GYDG$53,672 GYDG$55,761 GYDG$54,090 GYDG$49,704 GYDG$50,749 GYDG$55,552 GYDG$65,367 GYD
Avg. temp20°C22°C23°C25°C27°C28°C29°C29°C28°C27°C24°C22°C