
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! â§ 48 minutes from the Florida Keys. â§ 37 minutes from Miami Beach. â§ 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.

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 TVâs, 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. Youâll 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.

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. â 3 Comfortable BRs â Open Design Living â Fully Equipped Kitchen â Heated Pool â Game Room â Smart TVs â Smart House â High-Speed Wi-Fi â Free Parking

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.

Perfect for Families - The White House of Miami
Welcome to the White House of Miami This Is a Stunning Mega Home with 6,500 SqFt and an Amazing 1.25 Acre Lot With a private pool Truly Spacious, Modern and Clean. Enjoy your little slice of paradise. It has 9 Spacious Bedrooms and 6 Luxurious Bathrooms Perfect to Feel Comfortable and Safe This is a Great Place for Family Vacations, Friends, Romance or Group Getaways. Wake up listening to the singing of the birds and forget about the noise of the city

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. Itâs 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

âHave Fun at Hacienda ParaĂsoâ Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda ParaĂso. 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.

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

Kendall Keys Oasis w/ HEATED Pool Theater & Arcade

Private Pool and Tropical Garden Oasis

Spanish House 3 Bedroom Pool House

Beautiful Spacious 4 Bedroom Heated Pool

Spectacular Luxury Villa in Miami w/Pool/BBQ/Games

Luxury Oasis in Brickell - Only 3 min to Ocean

Miami Luxury Escape: Heated Pool, Jacuzzi & BBQ

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

*Coconut Grove Retreat: Balcony Pool, Free Parking

Ocean View Balcony. Pool & Hot tub. Fast Wi-Fi

Fontainebleau Jr. Suite King Bed with Ocean Views.

Gorgeous Beachy Chic Condo in Key Biscayne

Stylish Studio Icon, Waterfront Building

Front Facing Top Floor Penthouse with Ocean Views

Best area of Doral with all the services!

W HOTEL South Beach Luxury Ocean View Studio
Other holiday rentals with a pool

Heated Pool, Sleeps 11, Near Everglades

Spacious MIAMI private home with pool and parking.

Family retreat oasis, heated pool, jacuzzi & grill

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

South Miami Gem!

Tropical POOL Gateway! Midway to the Keys/ Miami

Private Villa âą Pool & Waterfall

Cozy house
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $399 NZD | $390 NZD | $463 NZD | $411 NZD | $418 NZD | $447 NZD | $465 NZD | $451 NZD | $414 NZD | $353 NZD | $373 NZD | $395 NZD |
| 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 $87Â NZD 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, Wi-Fi 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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- Rentals with a patio Cutler Bay
- Beachfront rentals Cutler Bay
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- House rentals Cutler Bay
- Rentals with pools Miami-Dade County
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- Rentals with pools United States
- South Beach
- Fort Lauderdale Beach
- Miami Design District
- Bayfront Park
- The Tides on Hollywood Beach
- Sea Air Towers Condominium Association
- Brickell City Centre
- Bayside Marketplace
- Miami Beach
- Miami Beach Convention Center
- Ritz-Carlton
- Kaseya Center
- Hard Rock Stadium
- Midtown
- Everglades National Park
- Fortune House Hotel
- Port Everglades
- Lummus Park
- University of Miami
- Haulover Beach
- Ocean Reserve Condominium
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- Las Olas Beach
- Lauderdale-By-The-Sea Beach




