
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$10,463 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.

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.

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.

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.

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 / 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.

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.

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

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.

“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

Welcome to Waltonhurst

Tropical Retreat Miami 5BR w/Pool, BBQ & GameRoom

Spacious MIAMI private home with pool and parking.

South Miami Gem!

Heated Pool Oasis • 12 Guests •Midway Keys & Miami

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

Chicness-Oasis

Private Villa • Pool & Waterfall
Condo rentals with a pool

Icon Brickell (W) Huge unit with bay & river views

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

Hotel Arya Apt w/Waterfront View, Free Parking

Cali King 1 BedRoom: Pool Gym Balcony Jacuzzi

Bay Views, Pool & Gym Access in Coconut Grove

Penthouse 1910 Ocean and Bay View 2BD Monte Carlo

Luxury 5 stars ICON Brickell @46TH 2B/2B, Pool/Gym

Best area of Doral with all the services!
Other vacation rentals with a pool

Family Villa w/ Heated Salt Pool • Near Key Largo

Everglades-Homestead. Tropical Retreat. Miami-Keys

Lake Of Dreams Miami House - The Perfect Place

Miami Oasis with Luxury Spa & Your Own Helicopter

3/2 Home with Pool & Bbq near Dadeland Mall

Casa Luna | Heated Pool |Private Retreat | 4BR

Waterfront Retreat•Heated Pool•Kayaks•Sleeps 11

Private Waterfront Studio Paradise
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$55,661 GYD | G$52,732 GYD | G$60,474 GYD | G$49,384 GYD | G$50,221 GYD | G$53,778 GYD | G$55,871 GYD | G$54,197 GYD | G$49,802 GYD | G$50,849 GYD | G$55,661 GYD | G$65,496 GYD |
| 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
- Hard Rock Stadium
- Port Everglades
- Bayfront Park
- Miami Beach Convention Center
- Everglades National Park
- Haulover Beach
- Brickell City Centre
- University of Miami
- Dolphin Mall
- Kaseya Center
- Sawgrass Mills
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- Seminole Hard Rock Hotel and Casino
- Midtown
- LoanDepot Park
- Bayside Marketplace
- Bal Harbour Beach
- Florida International University
- The Tides on Hollywood Beach
- John Pennekamp Coral Reef State Park
- Greater Fort Lauderdale Broward County Convention Center
- Aventura Mall





