Holiday rentals in Cutler Bay
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Quick stats about holiday rentals in Cutler Bay
Total holiday rentals
Explore 120 holiday rentals in Cutler Bay
Nightly prices starting at
Cutler Bay holiday rentals start at $39 SGD per night before taxes and fees
Verified guest reviews
Over 6,050 verified reviews to help you choose
Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 60 rentals that welcome pets
Holiday rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
120 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!
Top-rated holiday rentals in Cutler Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
The Pass Through - Brand New 2 | 1 Modern Villa
The Pass-Through is a cozy home located off of Florida’s Turnpike. Perfect if you’re looking for a pit stop when headed down to the Florida Keys or if you want to stay for a few days to explore Miami. Only a few minutes from Black Point Marina, where you can enjoy waterfront ambiance with outdoor seating, food, drinks, live band, and take your boat out for a ride to Biscayne Nat'l Park or Everglades Nat'l Park.Close to Florida’s Outlet Mall, authentic restaurants, wineries, freshfarms, and more.
Resort Style Pool • Fire Pit • PingPong • BBQ Fun!
Escape to Paradise in Cutler Bay, Florida! Experience the ultimate Florida lifestyle in our stunning getaway, perfectly situated for enjoying local events. 1-15 Min to Biscayne Bay 2-25 Min Brickell and Downtown 3- 30 Min to South Beach & Crandon Park Beach 4-Ideal for Families 5-Private Pool & Patio 6-Mediterranean Interior Design 7- Designed for 10 guests (1 King Bed, 1 Queen Bed , 2 Full bed , 1 Day Bed w/ 2 Twins)contact us 10- Fully Equipped Kitchen 11- Fast Wi-Fi 12- 24/7 Available Host
Cutler Bay Guest House
Cozy apartment in the heart of Cutler Bay. The guest house has a private entrance. Once you open the gate door you will find the door to the guest house. The kitchenette has a refrigerator, microwave, Keurig with coffee pods, and tea. The living area has a small sofa and a dinette.The room has a queen bed. The bathroom is is equipped with toiletries. It is located near Fairchild Tropical Garden, Black Point Marina, Homestead Speedway, Everglades National Park, Florida Keys, Zoo Miami and more.
Beautiful Family Villa. Large Outdoor Space & BBQ
Spacious 4BR, 2BA home in Cutler Bay with 5 comfy beds, full kitchen, washer & dryer, and a massive backyard! Enjoy the oversized outdoor space — perfect for playing sports, barbecues, or relaxing under the sun. Located in a peaceful area near shops, parks, and Black Point Marina. Ideal for families and groups seeking comfort, privacy, and a true South Florida experience. The home offers free parking, fast Wi-Fi, smart TVs, and plenty of room to unwind and make lasting memories together.
Miami Oasis with Luxury Spa & Your Own Helicopter
Spacious Miami villa perfect for families & groups! 6BR/4BA retreat sleeps 16 with heated pool, 8-seat jacuzzi & cedar sauna. Unique garden feature: a real U.S. Army Black Hawk helicopter for epic photos! Enjoy a chef’s kitchen, 75″ smart TV, gig-speed Wi-Fi, EV charger & parking. Relax on the tropical patio, fire up the BBQ grill, or sip espresso poolside. Just 20 min to Everglades, 30 min to Key Largo & South Beach. Book your private oasis today for an unforgettable Miami getaway!
Escape to Miami/Heather+Pool/9pl/BBQ/pool table.
🏡 Spacious Home with Heated Pool, BBQ & Game Room 🎉 Enjoy this perfect getaway for families and groups! 🛏 4 bedrooms: King, 2 Queen, and a bunk bed (Full + 2 Twin). 🚿 2.5 bathrooms. 🎱 Game room with pool table. 📺 TVs in all rooms, living room & patio. 👶 Crib & high chair available. 🍽 Fully equipped kitchen. 🏊♂️ Private heated pool 🔥. 🍖 BBQ & 🌿 2 hammocks in the patio. 🏠 Spacious, cozy, and perfect for relaxation. Book now for an unforgettable stay! ✨
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.
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
BayNest Cozy South Miami Suite Long Stay Friendly
Bay Nest is a peaceful, centrally-located private 1BD/1BA LUX Apartment in Miami, perfect for couples, solo travelers, and business guests. Enjoy a quiet retreat with a private entrance, fast Wi-Fi, comfortable bed, and a clean, stylish space ideal for relaxing or remote work. Conveniently located near major highways, shopping, dining, beaches, and local attractions, Bay Nest offers easy access to everything while providing a calm, home-like stay.
Family Oasis • Near Zoo & Marina | Pool_BBQ
With a prime location, this elegant 4BR/2BA home offers comfort, privacy, and a memorable stay from the moment you arrive. Its inviting atmosphere encourages relaxation, while thoughtfully designed spaces provide both comfort and practicality. Outdoors, enjoy comfortable seating areas perfect for unwinding, socializing, and experiencing Miami’s weather in a private, relaxing setting.
Chicness-Oasis
Welcome to your dream escape! A boho chic retreat blending laid-back luxury with natural charm. This haven features an open-plan living area, sunlit pool deck with plush daybeds, and a lush backyard with a whimsical tree swing. Thoughtfully designed for relaxation and style—perfect for families, couples, or creatives seeking a soulful getaway.
Paradise Home/Ideal Families /Grill / Bar
1- 3 Bedrooms (Sleeps 8 People) (1 King Bed, 1 Bunk Bed, 1 Twin Bed) 2- 25 Min to Key Largo 3- 25 Min to Miami Beach 4- 10 Min to Miami Metro Zoo 5- Homestead Speed Way 6- Private Parking 2 Cars 7- Fast Wifi 8- Laundry In Unit 9- Barbecue and Bar 10- Outdoor Dinning Area 11- Fully Equipped Kitchen 12- Ideal for Families
Popular amenities for Cutler Bay holiday rentals
Other great holiday rentals in Cutler Bay
Tropical Retreat Miami 5BR w/Pool, BBQ & GameRoom
Sweet Home
Tropical House Miami
Perfect 3 bedroom Home for Miami Getaway
Everglades-Homestead. Tropical Retreat. Miami-Keys
Lake Of Dreams Miami House - The Perfect Place
Heated Pool Oasis • 12 Guests •Midway Keys & Miami
Casa Luna | Heated Pool |Private Retreat | 4BR
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $229 SGD | $227 SGD | $233 SGD | $227 SGD | $207 SGD | $194 SGD | $229 SGD | $194 SGD | $194 SGD | $194 SGD | $233 SGD | $233 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 |
Frequently Asked Questions
What are the best places to stay in Cutler Bay?
Stays around lakeside neighborhoods, near parks, and in residential areas of Cutler Bay are frequently suggested for a peaceful experience. Many guests choose homes with easy access to outdoor spaces.
What are the best things to do in Cutler Bay with kids?
Families often explore playgrounds, splash pads, and nature trails in Cutler Bay. Black Point Park and Marina is frequently suggested for spotting birds, learning about local wildlife, and enjoying waterfront activities.
What are some of the best things to do in Cutler Bay?
Visitors explore local parks, kayak or boat in Biscayne Bay, and visit farmers markets on weekends. Many enjoy discovering neighborhood art and taking guided nature walks.
How is the weather in Cutler Bay?
Cutler Bay has warm, humid weather almost year-round, with temperatures ranging from 61–91°F (16–33°C). Rain is most frequent from late spring through early autumn, so an umbrella or rain jacket can be helpful.
When is the best time to visit Cutler Bay?
Late autumn and winter are often suggested for visiting Cutler Bay, as temperatures are milder and rainfall tends to be lower. Spring draws visitors with blooming gardens and outdoor events.
What are the best places to visit in Cutler Bay?
Cutler Bay has lush parks, community gardens, and access to Biscayne Bay for water activities. Popular spots often include Black Point Park and Marina, winding trails, and spaces for picnics or birdwatching.
What are some hiking trails in Cutler Bay?
Cutler Bay has walking and hiking paths in local parks such as Cutler Ridge Park and Black Point Park and Marina, where visitors wander through mangrove areas and scenic waterfront routes.
What are some family activities we can do in Cutler Bay?
Families explore local parks, playgrounds, and take part in community recreation programs in Cutler Bay. Visiting Black Point Park and Marina is also often recommended for wildlife spotting and waterfront fun.
What are some of the best day trip ideas from Cutler Bay?
Explore nearby nature preserves, take a trip to cultural attractions around Miami, or unwind at area beaches. The region also has gardens, wildlife centers, and local art galleries to discover.
Are there any pet friendly accommodations available in Cutler Bay?
Cutler Bay has pet-friendly accommodations, including homes with fenced yards and rentals near green spaces. Neighborhood parks around the area make visiting with pets convenient.
What are some local tips for visiting Cutler Bay?
Locals suggest exploring parks early to avoid midday heat and bringing sun protection for outdoor adventures. Sampling regional seafood and supporting area markets often adds to the experience.
What is Cutler Bay known for?
Cutler Bay is known for its coastal setting, local parks, and family-friendly neighborhoods. The area frequently draws visitors for boating, fishing, and exploring its green spaces.
What are the best hidden gems to explore in Cutler Bay?
Visitors often enjoy local nature trails, community art installations, and quiet waterfront picnic spots around Cutler Bay. Neighborhood farmers markets are a frequent weekend find.
What are the best foods to try in Cutler Bay?
Regional seafood dishes, Cuban-inspired cuisine, and tropical fruit smoothies are frequently suggested in Cutler Bay. Locally owned cafes and restaurants often serve specialties made with fresh area ingredients.
What should I bring for a trip to Cutler Bay?
Pack lightweight clothing, comfortable shoes for walking, and sun protection such as hats and sunscreen. A reusable water bottle is useful, especially during warmer months.
What is the nightlife in Cutler Bay like?
Cutler Bay has a laid-back nightlife scene with neighborhood bars, locally owned restaurants, and occasional live music. Many venues feature outdoor seating and a casual atmosphere.
What are the most popular events or festivals in Cutler Bay?
Cutler Bay’s calendar regularly features community celebrations, outdoor concerts, and neighborhood art fairs, especially during spring and early summer. Holiday parades and family-oriented festivals are also popular.
Are there family friendly vacation rentals in Cutler Bay?
Cutler Bay has many family-friendly vacation rentals, ranging from houses in quiet neighborhoods to condos near parks and playgrounds. Listings often highlight spacious layouts and amenities for children.
Destinations to explore
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- Rentals with a firepit Cutler Bay
- Rentals with pools 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
- 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
- Sawgrass Mills
- Las Olas Beach
- Seminole Hard Rock Hotel and Casino
- Midtown
- LoanDepot Park
- Bayside Marketplace
- Bal Harbour Beach
- Florida International University
- The Tides on Hollywood Beach
- John Pennekamp Coral Reef State Park
- Greater Fort Lauderdale Broward County Convention Center
- Aventura Mall