
Holiday rentals with a pool in Cutler Bay
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Cutler Bay

Total holiday rentals
Explore 50 holiday rentals in Cutler Bay

Nightly prices starting at
Cutler Bay holiday rentals start at $71 AUD per night before taxes and fees

Verified guest reviews
Over 3,080 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Cutler Bay holiday 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.

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.

Resort Style Pool House 5 Bed Mini-Golf Game-Room
Breathtaking Design: The entire private Home is equipped for up to 10 persons. It has 4 bedrooms, 6 beds, 4 bathrooms, and plenty of open natural lighting. Entertainment and family fun are guaranteed with access to a Gorgeous oversized Pool, Huge Backyard, Casino, Retro Games & Mini Golf Course Enjoy this home with its unique style and atmosphere for unforgettable vacations with your family. Ideal for large groups of friends & family looking for an excellent location without breaking the bank.

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.

Private Paradise between Miami & the Keys
My 4/3 home is in the area known as the "Gateway to the Keys". Enjoy a comfortable stay for 10 people in 4 bed rooms. Great place for families & travelers. Very comfy home, & the back yard has the feel of a true tropical paradise. Good WIFI. NO ADDITIONAL GUESTS & NO DJs. NO PARTIES. I RESERVE THE RIGHT TO ENTER THE HOME IF I FEEL THERE IS AN UNAUTHORIZED PARTY/EVENT. FINES WILL BE APPLIED FOR NOISE VIOLATIONS. We do not allow parties. UNAUTHORIZED parties can/will result in a $500 fine.

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

Oasis&Art/ArtificialBeach/HeatedPool/MiniGolf
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.

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

Ritz Resort | Pool/Spa/Gym/BBQ/Golf/FirePit/Arcade
🎨 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

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.

South Miami Gem • Mini Golf, Pool table & Pool_BBQ
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!

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.

“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.
Popular amenities for Cutler Bay rentals with a pool
House rentals with a pool

The Miracle Cottage & Pool on Acre Miami Florida

Cozy house

Luxury Resort Oasis & Heated Pool

Garden House, Pool in Lush Peaceful Homestead

The Lux Paradise Miami “Breakfast included”

| LuxeLanding | Pool+Lounge+Chess+BBQ+Golf+Airport

Kendall Keys Oasis w/ HEATED Pool Theater & Arcade

Family Home w/Pool •Gameroom•Private Park•Sleeps12
Condo rentals with a pool

Marriott Villas at Doral 2BD sleeps 8

Luxurious 2BR 3BA Walk to Beach Pool Jacuzzi

Hotel Arya Apt w/Waterfront View, Free Parking

39th Floor 3BR · Bay & City Views · Sleeps 8

Suite at The Ritz-Carlton Key Biscayne Miami

One Bedroom Condo King Bed With City Views

Beautiful apt. 1st floor 2/2. wifi and parking

Penthouse 1910 Ocean and Bay View 2BD Monte Carlo
Other holiday rentals with a pool

Tropical MIAMI Oasis BBQ/ Pool/Games and More

Cozy Suite -Exterior Entrance, SelfCheckin

Waterfront Retreat•Heated Pool•Kayaks•Sleeps 11

Private Villa • Pool & Waterfall

Everglades-Homestead. Tropical Retreat. Miami-Keys

Chicness-Oasis

Casa Luna | Heated •Pool Outdoor Oasis • Sleeps 12

Azure House Miami | Pool • Game Room • Gym
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $377 AUD | $357 AUD | $409 AUD | $385 AUD | $418 AUD | $384 AUD | $378 AUD | $367 AUD | $337 AUD | $344 AUD | $377 AUD | $443 AUD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Destinations to explore
- Miami Holiday rentals
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- Fort Lauderdale Beach
- South Beach
- Hard Rock Stadium
- Port Everglades
- Brickell City Centre
- Everglades National Park
- Bayfront Park
- Miami Beach Convention Center
- Haulover Beach
- Dolphin Mall
- University of Miami
- Kaseya Center
- Las Olas Beach
- Midtown
- Bayside Marketplace
- Sawgrass Mills
- LoanDepot Park
- The Tides on Hollywood Beach
- Bal Harbour Beach
- Greater Fort Lauderdale Broward County Convention Center
- Aventura Mall
- John Pennekamp Coral Reef State Park
- CG Cosmetic Surgery
- Amerant Bank Arena





