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Holiday rentals in Cutler Bay

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Top-rated holiday rentals in Cutler Bay

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

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Guest favourite
A refreshing outdoor pool is framed by palm trees and a surrounding patio of laid stones. Two loungers are positioned partially submerged in the water, complemented by a large umbrella for shade. The clear sky is visible above.
Home in Cutler Bay
4.95 out of 5 average rating, 161 reviews

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.

Top guest favourite
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
4.99 out of 5 average rating, 174 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 favourite
A serene outdoor space includes a swimming pool surrounded by terracotta tiles and lush tropical vegetation. A tiki hut is positioned in the background, with an evening sky showcasing warm tones of orange and yellow. Soft furnishings and a relaxed seating area are visible nearby.
Tiny home in Cutler Bay
4.97 out of 5 average rating, 269 reviews

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.

Superhost
A private heated pool is featured within a glass-enclosed backyard. The pool area is accented with colorful pool floats and a beach ball, while lounge chairs are positioned around the edge, creating an inviting space for relaxation or play.
Home in Cutler Bay
4.85 out of 5 average rating, 151 reviews

Luxury 7BR Retreat: BBQ/Court/Heated Pool & Fun

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!

Superhost
Home in Miami
4.86 out of 5 average rating, 256 reviews

Miami Oasis: Chill | Shop | Relax | Charming Home

A spacious and private retreat designed for families and group stays, our home in Palmetto Estates comfortably hosts up to 10 guests. We offer 3 well-appointed bedrooms, 2 full bathrooms, a bright living space, a fully equipped kitchen, laundry area, garage, and a covered patio with a large grassy yard. Located in a quiet neighborhood close to shopping, dining, Miami Zoo, the Everglades, and just 30 minutes from Downtown Miami, it’s an ideal base to explore South Florida.

Guest favourite
Flat in Cutler Bay
4.93 out of 5 average rating, 14 reviews

Hidden Gem. Luxe 1BR w/Patio

Welcome to Hidden Gem, a stylish 1BR retreat in Cutler Bay! Enjoy a 120” projector screen with Netflix & Prime, fast Wi-Fi, and a dedicated workstation. Relax in the rainfall shower or unwind on the LED-lit screened patio. Cook in your private kitchen, stay active with on-site workout equipment, and enjoy the spacious outdoor terrace & garden. Private entrance, parking, and washer/dryer included. Walk to a park in minutes and explore nearby shops, dining, and highways!

Top guest favourite
Guest suite in Homestead
4.98 out of 5 average rating, 104 reviews

“Explore at Hacienda Paraíso” Suite 2 | pool |

Welcome to Room 2, the second addition at Hacienda Paraíso. This beautiful suite is conveniently located next to another Airbnb suite, offering flexibility for your stay. We are happy to offer you a much larger space with a king size bed and queen size pullout couch making it easier to accommodate up to four people. The bathroom is very spacious with double sinks. You’ll also enjoy a beautiful view of the green front of the property and pool access.

Guest favourite
Home in Miami
4.93 out of 5 average rating, 152 reviews

Poolside Haven 4/2, Htd pool, oudr ktch by freeway

2 King beds, 1 queen bd, 2 double beds, 2 bath, heated pool, outdoor kitchen, self check in, fire pit Free private parking, fast wifi. Surround sound systems indoors and outdoors. Master bath with spa-style rainfall shower. Fully equipped kitchen with stainless steel appliances. Family-friendly: crib, playpen, highchair, infant car seat, safety gate. Quiet, established neighborhood.

Superhost
An outdoor dining area features a large rectangular table surrounded by four upholstered chairs, complemented by potted greenery at each end. A kitchen area with cabinetry and a countertop is visible in the background, set against a backdrop of brick walls and lush foliage.
Home in Princeton
4.81 out of 5 average rating, 110 reviews

To the Keys

Your family will be close to all these places if you stay in this centrally located accommodation to shop in stores with more than 50% discounts on the best brands, around the Southland Mall shopping centers, near Miami Zoo, Monkey Jungle, Pintos Farm, Brothers Farms, etc. As well as restaurants and more entertainment around it, you can contact me for more details if you wish

Guest favourite
Home in Cutler Bay
4.89 out of 5 average rating, 19 reviews

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.

Guest favourite
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.
Apartment in Palmetto Bay
4.92 out of 5 average rating, 318 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.

Guest favourite
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, 63 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

Popular amenities for Cutler Bay holiday rentals

When is the best time to visit Cutler Bay?

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Avg. price£133£136£149£132£121£113£134£113£113£113£136£136
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.

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 £15 per night before taxes and fees

  • Verified guest reviews

    Over 5,610 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

    60 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

  • 4.7 Average rating

    Cutler Bay stays receive an average rating of 4.7 out of 5 from guests

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