Holiday rentals in Cutler Bay
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Quick stats about holiday rentals in Cutler Bay
Total holiday rentals
Explore 130 holiday rentals in Cutler Bay
Nightly prices starting at
Cutler Bay holiday rentals start at £22 per night before taxes and fees
Verified guest reviews
Over 6,050 verified reviews to help you choose
Family-friendly holiday rentals
60 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
70 properties have a dedicated workspace
Wifi availability
130 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.
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
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
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 House 5 Bed Mini-Golf Game-Room
Breathtaking Design: The entire private Home is equipped for up to 10 persons. It has 4 bedrooms, 6 beds, 4 bathrooms, and plenty of open natural lighting. Entertainment and family fun are guaranteed with access to a Gorgeous oversized Pool, Huge Backyard, Casino, Retro Games & Mini Golf Course Enjoy this home with its unique style and atmosphere for unforgettable vacations with your family. Ideal for large groups of friends & family looking for an excellent location without breaking the bank.
Family Spacious Guest Suite 2Bed-Fits 4 Cutler Bay
✨ Modern Private Suite in Cutler Bay ✨ Independent & fully remodeled apt for 4 guests. 🛌 Master: King Bed + In-suite Bath + TV + Huge Walk-in closet. 🛋️ Living: Queen Sofa-bed . 🍳 Kitchen: Modern & fully equipped. ❄️ Mini-split AC. ☕ Patio: Large private area for coffee. 🚗 Driveway parking. 📍 Prime Location: 🚴 2m from Old Cutler Rd (Biking/Trails) 🚤 10m from Black Point Marina & Turnpike 🌳 100m from Recreational Park & Tennis 🏞️ Area with 3 lakes ideal for walking or biking! 🌴
Spacious Home by the Bay FAST Wi-Fi & Coffee
You will be steps away from Old Cutler Road and an abundance of unique dining and recreational options. Pay a visit to nearby attractions such as Southland Mall, The Falls Shopping Center, Black Point Marina, Deering Estates, Dennis C. Moss Cultural Center, Miami Metro Zoo, and more! ❧ 48 minutes away from the Florida Keys. ❧ 37 minutes away from Miami Beach. ❧ 33 minutes away from the Everglades National Park. Message us about long stay, military, & first responder discounts.
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
Casa Luna | Heated Pool |Private Retreat | 4BR
Welcome to Casa Luna – Your Private Oasis with a Heated Pool! Unwind in this stylish 4-bedroom, 3-bathroom home featuring a private pool, perfect for relaxing swims any time of year. Located in a quiet, family-friendly neighborhood in Cutler Bay, you're perfectly positioned between the Florida Keys and Downtown Miami. Whether you're here for adventure or relaxation, Casa Luna is the ideal home base for your South Florida getaway!
Vacation QJR
Relax in a stylish and elegant home offering comfort and sophistication. Enjoy serene rooms, premium bedding, full kitchen, fast WiFi, and a peaceful ambiance. A refined stay where you’ll feel indulged and at ease.Your family-friendly home away from home. Bright, cozy, safe, and comfortable, with fully equipped kitchen and inviting spaces to relax. Perfect for families, children, and longer stays. Calm area and great location.
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.
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
Sweet Home
Perfect 3 bedroom Home for Miami Getaway
Everglades-Homestead. Tropical Retreat. Miami-Keys
South Miami Gem!
Waterfront Retreat•Heated Pool•Kayaks•Sleeps 11
Chicness-Oasis
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 | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £132 | £130 | £134 | £130 | £119 | £112 | £132 | £112 | £112 | £112 | £134 | £134 |
| 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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