
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

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 • Near Zoo, The Falls | 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.

“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.

Private Miami Retreat/Htd Pool + Outdoor Kitchen
Private tropical retreat in Miami. 4BR · 2BA · sleeps 8. Heated pool, fire pit lounge, fully equipped outdoor kitchen & covered terrace. Master bath with spa rainfall shower. Surround sound indoors & outdoors. Stainless kitchen with pool views. Family-ready: crib, playpen, highchair, infant car seat & safety gate. Free parking · Fast WiFi · Self check-in. Superhost 4.93★ · 155 reviews. Quiet neighborhood.

Miami Lux Lake Front Retreat
A destination on its own: 1. Spacious home- over 5500 sqft of living space. 2. Gym with sauna and steam shower. 3. Pool table 4. Gourmet kitchen. 5. Formal dining room. 6. Large TV room with leather sectional, all recliner. 7. Karaoke 8. Kayaks to enjoy the lake 9. Heated Pool 10. Outdoor ping pong 🏓 table 11. Gym 12. Sauna and steam Room
Popular amenities for Cutler Bay rentals with a pool
House rentals with a pool

Family Paradise/11 ppl/HOT Pool/Soccer/Basketball

Heated Pool/Jacuzzi Paradise: Cozy Miami Retreat

3/2 Home with Pool & Bbq near Dadeland Mall

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

Casa Luna | Heated Pool |Private Retreat | 4BR

4BR Home with Pool, Playground & Boat/RV Parking

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

Backyard Escape | Heated Pool, Court & BBQ
Condo rentals with a pool

Modern Luxe at Brickell | Pool & Spa Access

Hotel Arya Apt w/Waterfront View, Free Parking

Oceanfront Brickell Miami Condo 33 Pool Free Parkg

Cali King 1 BedRoom: Pool Gym Balcony Jacuzzi

Guest Favorite Coconut Grove,pool, sauna,park free

Penthouse 1910 Ocean and Bay View 2BD Monte Carlo

Bay Views, Pool & Gym Access in Coconut Grove

Luxurious 2BR 3BA Walk to Beach Pool Jacuzzi
Other vacation rentals with a pool

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

Elegant House close to the Keys!

Family Villa w/ Heated Salt Pool • Near Key Largo

The Sunflower Inn

Hidden Gem. Luxe 1BR w/Patio

Luxury Villa • Racket Court • Gym • Grand Garden

Wanderlust Villa /Saltwater Heated Pool/pet/bbq

Maresma | 14PPL | Pool | Cinema |Sports Field |Gym
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$55,577 GYD | G$52,652 GYD | G$60,382 GYD | G$49,309 GYD | G$50,144 GYD | G$53,696 GYD | G$55,786 GYD | G$54,114 GYD | G$49,727 GYD | G$50,771 GYD | G$55,577 GYD | G$65,397 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 |
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$10,447 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!
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 washer and dryer Cutler Bay
- Beachfront rentals Cutler Bay
- Rentals with a fire pit Cutler Bay
- House rentals Cutler Bay
- Family-friendly rentals Cutler Bay
- Rentals with a patio Cutler Bay
- Rentals with outdoor seating Cutler Bay
- Rentals with lake access Cutler Bay
- Pet-friendly rentals 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
- Bayside Marketplace
- Kaseya Center
- The Tides on Hollywood Beach
- Brickell City Centre
- Miami Beach Convention Center
- Hard Rock Stadium
- Port Everglades
- Midtown
- Everglades National Park
- Haulover Beach
- University of Miami
- Ocean Reserve Condominium
- LoanDepot Park
- Las Olas Beach
- Lauderdale-By-The-Sea Beach
- Dolphin Mall
- Seminole Hard Rock Hotel and Casino
- Bal Harbour Beach
- Fort Lauderdale Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park





