
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 ﺩ.ﺇ 184 per night before taxes and fees

Verified guest reviews
Over 3,080 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.

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.

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.

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.

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.

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

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

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 • Pool_BBQ, Mini Golf & Pool table
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.

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.

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

Welcome to Waltonhurst

Escape to Miami/Heather+Pool/9pl/BBQ/pool table.

Luxury Stay w/ Heated Pool, Golf & Chess Yard

Casa Luna | Heated Pool |Private Retreat | 4BR

Private Villa • Pool & Waterfall

Garden House, Pool in Lush Peaceful Homestead

The Lux Paradise Miami

Luxury Resort | Gym, Cold Plunge, Jacuzzi & Sauna
Condo rentals with a pool

Studio at The Ritz-Carlton Key Biscayne Miami

Hotel Arya Apt w/Waterfront View, Free Parking

Oceanfront Brickell Miami Condo 33 Pool Free Parkg

Cali King 1 BedRoom: Pool Gym Balcony Jacuzzi

Lux 2BR • Water View • Pool • Spa • FREE Parking

Penthouse W/Bayviews! 2 Bdrm Condo In Miami Design

Bay Views, Pool & Gym Access in Coconut Grove

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

Villa Gaviota

Lake Of Dreams Miami House - The Perfect Place

Everglades-Homestead. Tropical Retreat. Miami-Keys

Luxury Villa • Racket Court • Gym • Grand Garden

3/2 Home with Pool & Bbq near Dadeland Mall

The Luxe Villa Miami Area/Private Pool/BBQ /Games

South Miami Gem!

Heated Pool Oasis • 12 Guests •Midway Keys & Miami
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 977 | ﺩ.ﺇ 925 | ﺩ.ﺇ 1,061 | ﺩ.ﺇ 867 | ﺩ.ﺇ 881 | ﺩ.ﺇ 944 | ﺩ.ﺇ 981 | ﺩ.ﺇ 951 | ﺩ.ﺇ 874 | ﺩ.ﺇ 892 | ﺩ.ﺇ 977 | ﺩ.ﺇ 1,149 |
| 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 |
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- Fort Lauderdale Beach
- Miami Beach - South Beach
- Port Everglades
- Hard Rock Stadium
- Bayfront Park
- Miami Beach Convention Center
- Everglades National Park
- Brickell City Centre
- Haulover Beach
- University of Miami
- Dolphin Mall
- Kaseya Center
- Sawgrass Mills
- Las Olas Beach
- Midtown
- Bayside Marketplace
- LoanDepot Park
- Bal Harbour Beach
- The Tides on Hollywood Beach
- John Pennekamp Coral Reef State Park
- Greater Fort Lauderdale Broward County Convention Center
- Aventura Mall
- Zoo Miami
- Dania Beach





