
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.

Miami Villa w/ Heated Pool, Games & BBQ 5BR
5 bedrooms / 3 bathrooms 2552 interior sq. ft 11,800 sq. ft Heated pool, Pool Table, Outdoor Kitchen with BBQ, Playgroun, Half Basketball Court, Outdoor Dining Table, mini beach, Mega Chess, Mini golf, Foosball, Fire Pit Come enjoy your next vacation in this beautiful modern property. Located in a wonderful and safe area,. The house has a fully equipped kitchen, smart TV in all bedrooms and living room, heated pool for you to enjoy the eternal Florida summer,Visiting Downtown Miami,South beach

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

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 Finest Pool Jacuzzi Amenities BBQ
Vibrant style and captivating design define every corner of this elegant home. White floors and walls, glass doors, and wooden tables contrast beautifully with colorful seating in the living and dining spaces. In the fully equipped chef-style kitchen, a complimentary bottle of wine elevates hospitality to an art form. This exceptional rental is truly unique, ideal for an inspiring getaway or corporate retreat. The neighborhood offers both safety and serenity.

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.

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

Family retreat oasis, heated pool, jacuzzi & grill

Encanto Family/Heated pool/center of Miami/BBQ

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

Incredible 49th Flr Bay & Pool Views | Free Spa!

Front Facing Top Floor Penthouse with Ocean Views

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

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

Your Bay View Escape in Coconut Grove, Pool & Gym

Penthouse 1910 Ocean and Bay View 2BD Monte Carlo

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

W Icon Brickell 40th Floor High Ceiling Ocean View
Other holiday rentals with a pool

Modern Casita

Hidden Gem. Luxe 1BR w/Patio

Waterfront Miami Oasis w/ Kayaks | Heated Pool

FirePit | Beach | Basketball | LuxuryVilla

South Miami Gem!

10 PPL | Luxury Farm | 20 Min Keys | Games | Event

Oasis&Art/ArtificialBeach/HeatedPool/MiniGolf

My beautiful home
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $299 SGD | $293 SGD | $347 SGD | $308 SGD | $313 SGD | $336 SGD | $349 SGD | $338 SGD | $311 SGD | $265 SGD | $280 SGD | $296 SGD |
| 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 $65 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Cutler Bay holiday rentals include wifi 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!
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- South Beach
- Fort Lauderdale Beach
- Bayfront Park
- Miami Beach Convention Center
- Hard Rock Stadium
- Everglades National Park
- Haulover Beach
- Port Everglades
- Bal Harbour Beach
- Miami Design District
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Dania Beach
- Ocean Terrace Public Beach
- Broward Center for the Performing Arts
- Jungle Island
- Phillip and Patricia Frost Museum of Science
- Key Biscayne Beach
- Crandon Beach
- Gulfstream Park Racing and Casino
- Biscayne National Park
- Biltmore Golf Course Miami
- Miami Beach Golf Club
- Coral Castle




