
Vacation 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.

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.

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

Luxury Miami Living - Heated Pool/Spa/Gym/BBQ/Fire Pit
🎨 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

Private Backyard Oasis • 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 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.

Cozy Suite -Exterior Entrance, SelfCheckin
If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Room for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel Safe and Welcome here! -GATEWAY to the Keys and Everglades -Private Entrance -Self Check-in -Free Parking -Fast WIFI -Bathroom with 2 sinks -SWIMMING POOL -Central A/C -HBO TV -Refrigerator -Ceiling Fan -Closet Space -Ceramic Tile Floors -Iron & Board -Towels & Bath essentials -Hair dryer

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.

“Explore at Hacienda Paraíso” Suite 2 | pool |
Welcome to Room 2, the second addition at Hacienda Paraíso. This beautiful suite is conveniently located next to another Airbnb suite, offering flexibility for your stay. We are happy to offer you a much larger space with a king size bed and queen size pullout couch making it easier to accommodate up to four people. The bathroom is very spacious with double sinks. You’ll also enjoy a beautiful view of the green front of the property and pool access.

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.

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
House rentals with a pool

Kid & Pet Friendly Pool Oasis | 15 min Zoo Miami

Private Paradise between Miami & the Keys

Perfect Miami Vacation | Heated Pool | Game Room

South Miami Gem!

Private Villa • Pool & Waterfall

BellaMoon Oasis Miami

Resort Style W/ Heated Pool, Games & Lux Services!

Sunny Getaway: Relaxing Miami Home
Condo rentals with a pool

Picasso | Penthouse WorldCenter - Brickell

Lovely 1 Bedroom apartment/Pool,Heart of Wynwood

Modern Luxe at Brickell | Pool & Spa Access

Luxury Condo in Hotel, amenities Downtown/Brickell

SF Beautiful Blue & Gold Studio with Ocean View

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

CityView Balcony Pool& Hottub. Wi-Fi. Full Kitchen

Marriott Villas and Doral 2BD sleeps 8
Other vacation rentals with a pool

Modern Casita

Grace Place Miami Heated Pool Theater 12 GUEST

Faena|16PPL|Multi-Sport|HotPool|Cinema|GymPlaygrou

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

Casa Luna | Heated Pool |Private Retreat | 4BR

Waterfront Miami Villa | Pool, Kayaks, Mini Golf

Chic-ness Oasis

4BR Home with Pool, Playground & Boat/RV Parking
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.ﺇ841 | ﺩ.ﺇ823 | ﺩ.ﺇ977 | ﺩ.ﺇ867 | ﺩ.ﺇ881 | ﺩ.ﺇ944 | ﺩ.ﺇ981 | ﺩ.ﺇ951 | ﺩ.ﺇ874 | ﺩ.ﺇ892 | ﺩ.ﺇ977 | ﺩ.ﺇ1,149 |
| 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 |
Quick stats about vacation rentals with a pool in Cutler Bay

Total vacation rentals
Explore 60 vacation rentals in Cutler Bay

Nightly prices starting at
Cutler Bay vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 3,120 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Cutler Bay vacation rentals include wi-fi 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
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Havana Vacation rentals
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Kissimmee Vacation rentals
- Rentals with a fire pit Cutler Bay
- Rentals with a patio Cutler Bay
- Pet-friendly rentals Cutler Bay
- Beachfront rentals Cutler Bay
- Rentals with a washer and dryer Cutler Bay
- Family-friendly rentals Cutler Bay
- Rentals with outdoor seating Cutler Bay
- House rentals Cutler Bay
- Rentals with lake access Cutler Bay
- Rentals with pools Miami-Dade County
- Rentals with pools Florida
- Rentals with pools United States
- Miami Beach - South Beach
- Fort Lauderdale Beach
- Bayfront Park
- The Tides on Hollywood Beach
- Bayside Marketplace
- Kaseya Center
- Brickell City Centre
- Miami Beach Convention Center
- Miami Beach
- Hard Rock Stadium
- Miami Design District
- Everglades National Park
- Port Everglades
- Midtown
- Haulover Beach
- University of Miami
- Calle Ocho Plaza
- Ocean Reserve Condominium
- Sawgrass Mills
- Las Olas Beach
- LoanDepot Park
- Lauderdale-By-The-Sea Beach
- Bal Harbour Beach
- Aventura Mall




