
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.

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!

Guest Suite-Exterior Entrance, SelfCheckin.
If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place 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 -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

Miami Getaway - Heated Pool, BBQ, Washer & Dryer
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 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.

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.

“Have Fun at Hacienda Paraíso” Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Marriott Villas and 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.

Charming Private Pool house for two.
Charming private back pool house on a fenced property in a quiet neighborhood close to US 1, the Turnpike, the Keys, Nascar and the Homestead Speedway, and the Everglades. You are 15-20 minutes from the Speedway, 20 minutes from the Everglades, and 30 minutes from Key Largo. For guests wishing to stay a month or more, I would require you to provide a copy of your photo ID.

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

Welcome to Waltonhurst

Kendall Keys Oasis w/ HEATED Pool Theater & Arcade

Private Pool and Tropical Garden Oasis

Lake Of Dreams Miami House - Your Favorite Place

Luxury Villa • Racket Court • Gym • Grand Garden

Hollywood Sunshine Resort Pool House w/ Hot tub

Cozy house

BellaMoon Oasis Miami
Condo rentals with a pool

Feels Like Summer ~ Panoramic Water Views! 2BR

SUNNY ISLES GORGEOUS 15A OCEAN FRONT (+hotel fees)

Luxury Beach & City View Condo 5 min walk to beach

Studio at The Ritz-Carlton Key Biscayne Miami

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

Fontainebleau Jr. Suite King Bed with Ocean Views.

Front Facing Top Floor Penthouse with Ocean Views

Penthouse 1909 Ocean and Bay View 1BD Monte Carlo
Other vacation rentals with a pool

Modern Casita

Family Fun •Huge Backyard •Heated Pool •Cinema

Hidden Gem. Luxe 1BR w/Patio

Habitat Privé The Majestic Tree

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

Casa Luna |Heated Pool |Private Retreat | 4BR

Glamping Paradise in Cutler Bay

Modern Mobile 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 | ﺩ.ﺇ841 | ﺩ.ﺇ823 | ﺩ.ﺇ977 | ﺩ.ﺇ867 | ﺩ.ﺇ881 | ﺩ.ﺇ944 | ﺩ.ﺇ981 | ﺩ.ﺇ951 | ﺩ.ﺇ874 | ﺩ.ﺇ746 | ﺩ.ﺇ786 | ﺩ.ﺇ834 |
| 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 3,500 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

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