
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.

Make It Happen! Brand New with Amazing Water Views
Bluewater Realty Miami welcomes you to The Grand, located in Downtown Miami on Biscayne Bay. Our 2 bedroom Make It Happen! is the ultimate retreat, equipped with everything you could need. Enjoy views of Biscayne Bay and Margaret Pace Park that will leave you in awe. With South Miami Beach 3 miles away you can indulge in the sun of Miami Beach while still feeling the energy of downtown Miami, giving you the ultimate Miami experience. Your Airbnb Superhosts, Rachel and Mia Bluewater Realty Miami

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 private guest studio
Welcome! This is a private guesthouse located in a quiet neighborhood. Accommodations are with a private entrance and parking space to make you feel at home. We are located near a major expressway. We have a pool; The POOL is a SWIM AT YOUR OWN RISK. It is shared with Owner. Enjoy a smoke free cottage. Ashtrays are provided outside for those guest that do smoke. We provide a queen size bed and a couch/bed. This space is perfect and comfortable for two guest.Please NO children and NO animals.

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. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Luxury Villa | Spa - Pool |Top Location| Pets |BBQ
Welcome to Jessica and Javier House in Miami! We want to Be your Hosts ! Let us show you why you should book with us: - 2000 ft2 ground floor house - 3BDR Designed for 12 guests - 5 Min to Zoo - 20 Min to Coral Gables and Little Havana - 25 Min to Beach - 30 Min to Miami Airport - Residential Area - Private Pool - Spa - Fast WIFI - Fully equipped kitchen - Dedicated work space - Free Onsite parking - BBQ - Outside dining - Washer & Dryer - Kids and Pet friendly - 2 Sofa beds - Family games

Very Private 1/1 Apt w/Oasis Pool Patio Setting
Private apartment-1 bedroom w/king size bed, 1 full size bathroom, separate living and dining area. Fully equipped kitchen. Free parking, beautiful oasis setting with salt water pool, hot tub & patio. Gazebo w/fire pit, Bar-be-cue, 2 TV’s, free WiFi. This is NOT a party spot but a place to relax in the pool, hot tub or relaxing dinners at home after visiting Miami venues. Set in a quiet neighborhood, 2 miles from shopping & restaurants. This is your home away from home vacation spot!

NEW! "Villa Paradise" ~ Lux 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

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

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.

Marriott Villas at Doral 2BD sleeps 8
Located in one of the most prestigious areas of Miami, Marriott's Villas at Doral are a tranquil hideaway; only 13 miles from the sizzling excitement of Miami Beach, yet a world away. Sharing the 650-acre lush landscape is the celebrated Trump National Doral Miami, a Trump-managed resort. There, you have access to four championship courses, a classic European spa, a water recreation playground and several restaurants.

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

Casa Cascada in Coral Gables Area

Welcome to Waltonhurst

Andy Resort Inc-Flash Sale

Elegant House close to the Keys!

Private Pool and Tropical Garden Oasis

Encanto Family/Heated pool/center of Miami/BBQ

Charming house with private pool & large patio

3B/2B Tropical Oasis w Salt-Water Pool! Lake views
Condo rentals with a pool

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

Fontainebleau Jr. Suite King Bed with Ocean Views.

Modern Luxe at Brickell | Pool & Spa Access

W HOTEL SOUTH BEACH LUXURY 1B RESIDENCE OCEAN VIEW

Upper Penthouse Corner Unit 2B/2B | Icon Brickell

Stunning 2 bedroom+17 foot ceilings & heated pool

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

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

Modern Casita

Waterfront Miami Oasis w/ Kayaks | Heated Pool

FirePit | Beach | Basketball | LuxuryVilla

South Miami Gem!

Tropical Paradise Between Miami and the FL Keys

Oasis&Art/ArtificialBeach/HeatedPool/MiniGolf

Mi casa bonita

4BD 3.5BA︱Heated Pool︱Arcade︱Family Getaway
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $347 AUD | $339 AUD | $403 AUD | $357 AUD | $363 AUD | $389 AUD | $404 AUD | $392 AUD | $360 AUD | $307 AUD | $324 AUD | $344 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 $76 AUD per night before taxes and fees

Verified guest reviews
Over 3,500 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, Wi-Fi and Pool across Cutler Bay rentals

4.8 Average rating
Cutler Bay stays are highly rated by guests—averaging 4.8 out of 5!
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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Miami Beach Convention Center
- Hard Rock Stadium
- Miami Design District
- Everglades National Park
- Haulover Beach
- Port Everglades
- Bal Harbour Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
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- Broward Center for the Performing Arts
- Phillip and Patricia Frost Museum of Science
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