
Holiday 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.

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.

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

Private Waterfront Studio Paradise
Casa Cocos is a private studio, with a private entrance, bathroom and kitchenette, and free and secure parking. It is nestled in Florida's tropical waterfront paradise. Come enjoy the views of the garden, go for a swim, paddle board, canoe, kayak, grill, take a nap in a hammock, and just relax. Casa Cocos is surrounded by nearby restaurants, bars, retail stores, malls all within walking distance or a short drive. 30 minutes to airport, downtown, South Beach, Keys, and Everglades.

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.

Poolside Haven 4/2, Htd pool, oudr ktch by freeway
2 King beds, 1 queen bd, 2 double beds, 2 bath, heated pool, outdoor kitchen, self check in, fire pit Free private parking, fast wifi. Surround sound systems indoors and outdoors. Master bath with spa-style rainfall shower. Fully equipped kitchen with stainless steel appliances. Family-friendly: crib, playpen, highchair, infant car seat, safety gate. Quiet, established neighborhood.

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

Renaissances Ranches pool house

Heated Pool, Sleeps 11, Near Everglades

Chic-ness Oasis

Charming house with private pool & large patio

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

Luxury Oasis in Brickell - Only 3 min to Ocean

BellaMoon Oasis Miami

Private Villa • Pool & Waterfall
Condo rentals with a pool

Studio at The Ritz-Carlton Key Biscayne Miami

SF Stunning 12th Flr. Studio in the Heart of Grove

Modern Luxe at Brickell | Pool & Spa Access

NEW 1BR in Miami Beach, Walk to Beach, Resort

Luxury Condo in Hotel, amenities Downtown/Brickell

Stunning 2 bedroom+17 foot ceilings & heated pool

Luxurious One Bedroom at Brickell Arc

Luxury 5 stars ICON Brickell @46TH 2B/2B, Pool/Gym
Other holiday rentals with a pool

Family Villa w/ Heated Salt Pool • Near Key Largo

Everglades-Homestead. Tropical Retreat. Miami-Keys

Dream Miami Stay | Heated Pool | Game Room

Paradise in Palmetto Bay, with Pool-BBQ-Gazebo.

Casa Luna | Heated Pool |Private Retreat | 4BR

Quaint 3-bedroom home with a pool.

Charming villa/Large pool/BBQ/Game room/basketball

Luxury Escape: Pool, Hot Tub, Mini Golf & More!
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $324 AUD | $317 AUD | $376 AUD | $334 AUD | $340 AUD | $364 AUD | $378 AUD | $366 AUD | $337 AUD | $344 AUD | $376 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 |
Quick stats about holiday rentals with a pool in Cutler Bay

Total holiday rentals
Explore 60 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 3,120 verified reviews to help you choose

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

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Cutler Bay holiday 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
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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- The Tides on Hollywood Beach
- Bayside Marketplace
- Brickell City Centre
- Miami Beach Convention Center
- Miami Design District
- Miami Beach
- Kaseya Center
- Hard Rock Stadium
- Everglades National Park
- Midtown
- Port Everglades
- Haulover Beach
- University of Miami
- Ocean Reserve Condominium
- Calle Ocho Plaza
- Sawgrass Mills
- Las Olas Beach
- LoanDepot Park
- Lauderdale-By-The-Sea Beach
- Bal Harbour Beach
- Aventura Mall




