Vacation rentals in Cutler Bay
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Quick stats about vacation rentals in Cutler Bay
Total vacation rentals
Explore 130 vacation rentals in Cutler Bay
Nightly prices starting at
Cutler Bay vacation rentals start at $42 CAD per night before taxes and fees
Verified guest reviews
Over 6,050 verified reviews to help you choose
Family-friendly vacation rentals
60 properties offer extra space and 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
70 properties have a dedicated workspace
Wifi availability
130 of Cutler Bay vacation 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 vacation rentals in Cutler Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.
Boutique Style House Hot-Tub Mini-Golf BBQ & Games
Come enjoy this beautiful vacation townhouse with 3 bedrooms, 2.5 bathrooms in Homestead - Miami with a large parking driveway. This is a tropical paradise close to everything needed to live the good life! Great location close to Miami Zoo, Homestead Speedway, and US1 to the Florida Keys The property sleeps up to 8 guests and is ideal for a group of friends or family looking to experience all the sunshine and fun that South Florida has to offer. Property is located in 137 Avenue and 260th Lane
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.
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
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 Big Outdoor BBQ Pool table
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.
South Miami Gem • Pool_BBQ, Mini Golf & Pool table
Discover the pinnacle of modern living in this newly remodeled 7-bedroom, 4-bath masterpiece. With sleek architecture and designer touches, this South Miami retreat offers a private heated pool and resort-style amenities for a truly unforgettable stay. Perfectly situated near stunning beaches, the Miami Zoo, Southland Mall, and top attractions, it’s your gateway to the best of South Florida. Experience unmatched comfort and sophistication—this one-of-a-kind home awaits you!
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
Luxury Backyard Escape | Heated Pool | Court | BBQ
Heated pool/ half basketball court/ pool table/ BBQ area/ playground/ sun loungers/ pergola with outdoor furniture Do not miss an incredible vacation in Miami in this beautifully renovated home with an open concept, designed for you to enjoy with family and friends. It features 5 bedrooms, 3 full bathrooms, and space for 12 guests. Enjoy comfortable rooms with memory foam mattresses, Smart TVs, and a fully equipped kitchen.
Private Villa • Pool & Waterfall
Spacious 4BR/4.5BA villa with 5,000 sq ft of fun. Enjoy a spa-style pool, BBQ with outdoor TV, ping pong, pool table, axe throwing (safe), and more. Every room has a Smart TV. Beaches and marina nearby. Private access, big driveway, and full guest access. Perfect for families or groups looking to relax, play, and enjoy Miami in comfort.
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.
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
Heated Pool Oasis • 12 Guests •Midway Keys & Miami
🌴 Casa Madrisquí | Heated Pool Oasis • Midway to Keys & Miami ✨ Your private tropical escape in South Miami 🌞 Perfect for families, groups, and wedding stays, with a HEATED pool, outdoor entertainment, and unbeatable location between the Florida Keys & Miami Beach.
Popular amenities for Cutler Bay vacation rentals
Other great vacation rentals in Cutler Bay
Rooftop Oasis 𓇼𓆉︎ near The Keys & The Everglades
Lake Of Dreams Miami House - The Perfect Place
Everglades-Homestead. Tropical Retreat. Miami-Keys
Chicness-Oasis
Waterfront Retreat•Heated Pool•Kayaks•Sleeps 11
Casa Luna | Heated Pool |Private Retreat | 4BR
Studio Private Entry close to Blackpoint Marina
Resort Style W/ Heated Pool, Games & Lux Services!
When is the best time to visit Cutler Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $249 CAD | $247 CAD | $254 CAD | $247 CAD | $225 CAD | $211 CAD | $249 CAD | $211 CAD | $211 CAD | $211 CAD | $254 CAD | $254 CAD |
| 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.
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