
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.
FamilyLocationIndoor spaces

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.
ValueLocationCheckout

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.
LocationFamilyBathroom

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.
LocationValueOutdoor spaces

Oasis&Art/ArtificialBeach/HeatedPool/MiniGolf
House in Miami, Sleeps 12 Heated Pool/Mini Golf/Kids Playground/BBQ/Cornhole game/Small beach/mini football Ned/Hammocks. Peace, nature, fun and more you will find in our house. The house is decorated with unique original art. Don't miss out on this newly remodeled cozy home, an ideal retreat for a peaceful and rejuvenating vacation. With a spacious living room, dining area, and a fully equipped kitchen, this house has everything you need. Nestled in a secure and tranquil neighborhood.
LocationFamilyBathroom

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
LocationValueNearby

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.
FamilyValueHospitality

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.
FamilyLocationParking

Family Oasis Retreat• Heated 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 heated 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.
LocationValueWalkability

Heated Pool/Jacuzzi Paradise: Cozy Miami Retreat
Welcome to our spacious 3 bedroom, 2 bathroom home located in the highly desirable Cutler Bay neighborhood! The home is perfect for families, couples, or friends looking for a comfortable getaway. Our home boasts a large pool with an attached Jacuzzi and a screened-in pool area perfect for enjoying the Florida sun. ✔ Fully Equipped Kitchen ✔ Comfortable Bedrooms with King/Queen/Full beds ✔ Open Concept Living Area ✔ Office Desk ✔ Piano ✔ High-Speed Wi-Fi
FamilyValueBarbecue

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.
LocationFamilyWalkability

Modern 5BR Oasis • Pool & BBQ | Near Redland & Zoo
Escape to your private tropical oasis in Miami. Enjoy a private pool, mini golf, BBQ nights under a tropical pergola, and hours of fun with billiards & ping pong. Start your stay with a complimentary welcome bottle of wine and the ease of self check-in. Located in a quiet central area, close to South Beach, the Florida Keys, and Miami Zoo. Perfect for families, couples, business trips, or groups seeking comfort, fun & privacy.
LocationValueSleep quality
Popular amenities for Cutler Bay rentals with a pool
House rentals with a pool

Welcome to Waltonhurst
FamilyLocationTV

Tropical Retreat Miami 5BR w/Pool, BBQ & GameRoom
LocationValueIndoor spaces

Family Villa w/ Heated Salt Pool • Near Key Largo
LocationValueGetting around

Everglades-Homestead. Tropical Retreat. Miami-Keys
FamilyValuePool

South Miami Gem!
FamilyLocationDecor

Escape to Miami/Heather+Pool/9pl/BBQ/pool table.
FamilyLocationDecor

Casa Luna | Heated Pool |Private Retreat | 4BR
ValueFamilyNearby

Chicness-Oasis
FamilyLocationKitchen
Condo rentals with a pool

Oceanfront Brickell Miami Condo 33 Pool Free Parkg
FamilyLocationAccess

Cali King 1 BedRoom: Pool Gym Balcony Jacuzzi
ValueLocationKitchen

Key Biscayne little beach place
LocationValueDecor

W HOTEL SOUTH BEACH LUXURY 1B RESIDENCE OCEAN VIEW
LocationValueParking

SF Beautiful Blue & Gold Studio with Ocean View
FamilyLocationAccuracy

Penthouse 1910 Ocean and Bay View 2BD Monte Carlo
LocationFamilyHeating

Bay Views, Pool & Gym Access in Coconut Grove
ValueFamilyLaundry

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

Family Oasis: Pool, Spa, Sauna + Kids Play Area
FamilyComfortHot tub

Lake Of Dreams Miami House - The Perfect Place
FamilyValueKitchen

3/2 Home with Pool & Bbq near Dadeland Mall
FamilyLocationHospitality

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

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

Heated Pool Oasis • 12 Guests •Midway Keys & Miami
FamilyValueDecor

Waterfront Retreat•Heated Pool•Kayaks•Sleeps 11
FamilyLocationQuiet

Luxury Escape: Pool, Hot Tub, Mini Golf & More!
LocationFamilyWalkability
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $379 AUD | $359 AUD | $412 AUD | $337 AUD | $342 AUD | $367 AUD | $381 AUD | $369 AUD | $339 AUD | $347 AUD | $379 AUD | $446 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 50 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 3,340 verified reviews to help you choose

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

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Cutler Bay holiday 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!
Destinations to explore
- Rentals with a fire pit Cutler Bay
- Rentals with a washing machine and dryer Cutler Bay
- Pet-friendly rentals Cutler Bay
- Rentals with a patio Cutler Bay
- Family-friendly rentals Cutler Bay
- Rentals with outdoor seating Cutler Bay
- Beachfront rentals Cutler Bay
- Rentals with lake access Cutler Bay
- House rentals Cutler Bay
- Rentals with pools Miami-Dade County
- Rentals with pools Florida
- Rentals with pools United States
- Fort Lauderdale Beach
- South Beach
- Hard Rock Stadium
- Port Everglades
- Bayfront Park
- Miami Beach Convention Center
- Everglades National Park
- Haulover Beach
- Brickell City Centre
- University of Miami
- Dolphin Mall
- Kaseya Center
- Las Olas Beach
- LoanDepot Park
- Sawgrass Mills
- Seminole Hard Rock Hotel and Casino
- Midtown
- Bayside Marketplace
- Bal Harbour Beach
- Florida International University
- The Tides on Hollywood Beach
- Aventura Mall
- Lauderdale-By-The-Sea Beach
- John Pennekamp Coral Reef State Park





