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Vacation rentals in Cutler Bay

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Quick stats about vacation rentals in Cutler Bay

  • Total vacation rentals

    Explore 120 vacation rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay vacation rentals start at G$6,270 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,050 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 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!

Top-rated vacation rentals in Cutler Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Princeton
5 out of 5 average rating, 22 reviews

Miami Relax | Heated Pool | Family Getaway.

Welcome to your peaceful getaway in South Miami. Our home offers comfort, relaxation, and a true feel-at-home experience. Enjoy the heated pool, unwind after a day out, and relax in a quiet, safe neighborhood. Perfect for families and couples seeking rest and quality time together. With quick access to the Turnpike and just 8 minutes from Black Point Marina, the location offers the perfect balance between convenience and tranquility. Clean, cozy, and welcoming — book with confidence. Enjoy it no

Guest favorite
An outdoor space is highlighted by a wooden picnic table and a cozy sofa underneath a large umbrella. String lights are illuminated above, creating a warm ambiance. Stepping stones set in dark rocks lead through the greenery, providing a tranquil setting for relaxation.
Villa in Homestead
4.98 out of 5 average rating, 192 reviews

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.

Top guest favorite
Guesthouse in Cutler Bay
4.96 out of 5 average rating, 25 reviews

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.

Top guest favorite
Home in Cutler Bay
5 out of 5 average rating, 28 reviews

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.

Guest favorite
The outdoor area features a heated pool surrounded by colorful murals, with a jacuzzi nearby. Poolside loungers and a basketball hoop are visible, offering a vibrant space for relaxation and fun under a clear blue sky.
Home in Miami
4.93 out of 5 average rating, 123 reviews

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.

Superhost
A screened-in pool area showcases a large pool and an attached hot tub. Lounge chairs are positioned around the pool, while a dining table with chairs is visible nearby. Lush greenery surrounds the space, creating a tranquil outdoor atmosphere.
Home in Cutler Bay
4.77 out of 5 average rating, 145 reviews

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

Superhost
Home in Cutler Bay
4.81 out of 5 average rating, 160 reviews

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.

Guest favorite
A serene waterfront view is presented, with clear water reflecting the surrounding greenery and buildings. An elegant dining area features a glass table surrounded by stylish chairs. The staircase leads to well-lit hallways, while a comfortable bedroom displays a spacious bed and decorative furnishings.
Home in Cutler Bay
4.86 out of 5 average rating, 29 reviews

Perfect 3 bedroom Home for Miami Getaway

Relax in this cozy, fully equipped home featuring a spacious living area, modern kitchen, and comfortable bedrooms ideal for families or small groups. Perfectly located just steps from Old Cutler Road, surrounded by unique dining, shopping, and top attractions like Southland Mall, The Falls, Black Point Marina, Deering Estates, Everglades National Park, and Miami Beach.

Guest favorite
A shaded cabana is positioned by the pool, featuring a wooden frame with draped fabric. Surrounding the pool are several lounge chairs arranged under large umbrellas. Lush greenery and flowering plants are visible in the background, enhancing the serene outdoor space.
Home in Cutler Bay
5 out of 5 average rating, 21 reviews

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.

Guest favorite
A modern studio apartment features an open layout with a well-equipped kitchen and seating for two at a sleek countertop. A cozy couch sits across from a queen bed, with a light rug underfoot. Natural light enters through a window framed by horizontal blinds.
Condo in Palmetto Bay
4.92 out of 5 average rating, 334 reviews

Bright Modern Studio Apartment

Find yourself at this slick Studio Apartment professionally designed, top of the art appliances with a unique modern touch. Based in a quiet and peaceful neighborhood. Located close to Downtown Miami and also to The Florida Keys. Nearby shoppings centers, restaurants and supermarkets. All you need to enjoy a charming getaway.

Top guest favorite
A modern living room is depicted, featuring a large white sofa adorned with patterned cushions. A round coffee table sits on a decorative rug featuring swirling patterns. A wall-mounted television displays an image of a serene scene, while a small plant adds a touch of greenery.
Home in Cutler Bay
4.92 out of 5 average rating, 77 reviews

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

Guest favorite
A studio apartment features a spacious bed with soft linens and a ceiling fan for comfort. A dining area with a table and chairs is positioned beside a compact kitchen that includes a refrigerator and microwave. A wardrobe is visible, providing storage options.
Guesthouse in Cutler Bay
4.88 out of 5 average rating, 64 reviews

Studio Private Entry close to Blackpoint Marina

Welcome to our cozy and convenient short-term rental studio apartment, where comfort meets functionality in every square foot. Nestled in a serene neighborhood, this charming abode offers a retreat-like ambiance perfect for solo travelers or couples seeking a home away from home.

Popular amenities for Cutler Bay vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Cutler Bay

Guest favorite
Home in Miami
4.97 out of 5 average rating, 34 reviews

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

Guesthouse in Cutler Bay
4.87 out of 5 average rating, 52 reviews

Home Sweet Home

The outdoor area features a spacious swimming pool surrounded by a tiled patio. Lounge chairs are positioned for relaxation. Lush palm trees provide shade, while a covered seating area is visible in the background. Bright blue skies enhance the inviting ambiance of the space.
Home in Cutler Bay
4.84 out of 5 average rating, 194 reviews

Tropical House Miami

Superhost
A serene outdoor space features a large, clear pool surrounded by lush greenery and palm trees. A pathway leads down to the pool area, showcasing geometric patterns in the stonework. A shaded seating area is visible in the background, enhancing the tranquil atmosphere.
Home in Miami
4.84 out of 5 average rating, 51 reviews

Lake Of Dreams Miami House - The Perfect Place

Guest favorite
Villa in Cutler Bay
4.94 out of 5 average rating, 84 reviews

Miami Oasis with Luxury Spa & Your Own Helicopter

A cozy sleeping area features a spacious bed covered with a light quilt. Soft lighting is provided by two bedside lamps on turquoise tables. A large framed artwork of a serene ocean scene hangs above the bed, complemented by a stylish black and white patterned closet door.
Guest suite in Cutler Bay
4.82 out of 5 average rating, 558 reviews

Private 1bd/1bath guest suite.

Top guest favorite
Home in Princeton
4.96 out of 5 average rating, 28 reviews

Heated Pool Oasis • 12 Guests •Midway Keys & Miami

Top guest favorite
Villa in Cutler Bay
4.96 out of 5 average rating, 56 reviews

Waterfront Retreat•Heated Pool•Kayaks•Sleeps 11

When is the best time to visit Cutler Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$36,991 GYDG$36,573 GYDG$37,617 GYDG$36,573 GYDG$33,438 GYDG$31,348 GYDG$36,991 GYDG$31,348 GYDG$31,348 GYDG$31,348 GYDG$37,617 GYDG$37,617 GYD
Avg. temp20°C22°C23°C25°C27°C28°C29°C29°C28°C27°C24°C22°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

  1. Airbnb
  2. United States
  3. Florida
  4. Miami-Dade County
  5. Cutler Bay