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Vacation rentals in Cutler Bay

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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 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, 168 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.

Guest favourite
A spacious suite featuring a king size bed with crisp white linens. Dark accent walls provide contrast against light wooden flooring. Natural light enters through large windows adorned with sheer curtains, while a small desk and tasteful decorative elements complete the stylish environment.
Apartment in Coconut Grove
4.81 out of 5 average rating, 126 reviews

Coconut Grove Stunning City View Suite Free Park

INCREDIBLE VALUE! First, a $30 gift card to our restaurant GreenStreet and a bottle of champagne will be awaiting you in your room! In Coconut Grove, this privately owned & renovated bright suite on the 15th floor of a luxurious waterfront property offers breathtaking city views, is fully equipped for 2 w/ a king size bed & full bath. Enjoy all the luxury amenities this property has to offer, pool & hot-tub with incredible bay views, penthouse gym, sauna, business center, 24-hr security, squash

Top guest favourite
A spacious driveway curves past vibrant tropical plants and palm trees leading to a welcoming entrance of the property. The house features a warm orange exterior with decorative elements and a large garage door, complementing the lush landscaping.
Guest suite in Miami
4.9 out of 5 average rating, 389 reviews

Guest Suite-Exterior Entrance, SelfCheckin.

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Place for you. We are conveniently located between Key Largo and Downtown Miami, in an upscale community. You’ll feel safe and welcome here! -GATEWAY to the Keys and Everglades -Private entrance -Self Check-in -Free Parking -Fast WIFI -Swimming Pool -Central A/C -Ceiling fan -Kitchenette -Refrigerator -Microwave -Coffee maker -Netflix-HBO TV -Ceramic Tile Floors -Full Closet -Towels/Bath essentials -Iron & Board

Top guest favourite
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
4.97 out of 5 average rating, 102 reviews

Family retreat oasis, 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 & electric car connection.

Guest favourite
An open kitchen area features gray cabinetry and a stylish marble countertop. A dining table is set for four, complete with white dishes and black placemats. Stainless steel appliances, including a refrigerator and oven, provide modern convenience, while a cozy living room is visible in the background.
Home in Cutler Bay
4.93 out of 5 average rating, 133 reviews

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.

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 homes in Cutler Bay
4.98 out of 5 average rating, 261 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.

Top guest favourite
A colorful hammock is suspended between two palm trees, inviting relaxation beside a sparkling pool. Lush tropical plants surround the outdoor area, creating a peaceful ambience. The inviting pool area is visible in the background, enhancing the serene outdoor setting.
Guest suite in Homestead
4.99 out of 5 average rating, 175 reviews

“Have Fun at Hacienda Paraíso” Suite 1 | pool |

Welcome to Room 1, the first addition at Hacienda Paraíso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

Guest favourite
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 Miami
4.83 out of 5 average rating, 103 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
A well-lit studio room features a full-size bed with light bedding topped by two pillows. A small dining area with two chairs and a round table is positioned near the window, which is covered by bright, modern shades. Storage is provided by a closet.
Guesthouse in Miami
4.96 out of 5 average rating, 235 reviews

Alma

This completely new studio has a private entrance and private outdoor space to enjoy your stay in Miami. Located at Palmetto Bay, in a very quiet area between Key Largo and Downtown Miami, perfect for travelers that planning visiting Miami, Everglades, the Keys, and our great Beaches. This cozy space is perfect for couples, solo adventures, and business travelers.

Guest favourite
Guesthouse in Miami
4.88 out of 5 average rating, 161 reviews

Modern Private Room | Super Clean and Quiet Stay

Modern, private, and cozy studio in Miami! Enjoy your own entrance, private bathroom, and a comfy Queen bed. Fully remodeled with Smart TV, microwave, coffee maker, large fridge, blender, and dishware. Just minutes from Zoo Miami and close to major highways, with free private parking. Perfect for couples, business travelers, or a weekend getaway.

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.
Condo in Palmetto Bay
4.91 out of 5 average rating, 312 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.

Superhost
The room features a spacious bed with a white headboard, adorned with blue accent pillows. On either side, white nightstands hold lamps that emit a soft glow. A plant adds a touch of greenery, complementing the muted blue walls.
Guest suite in Princeton
4.83 out of 5 average rating, 155 reviews

Modern Private Room (Not Shared )

Kick back and relax in this quite, and beautifully decorated private room. You’ll feel like you’re in a hotel room! It is cozy, clean and welcoming. Our amazing master bedroom has a private bathroom and a private entrance to give you privacy. Perfect to relax in our Queen bed after a long day 🙂

Popular amenities for Cutler Bay vacation rentals

When is the best time to visit Cutler Bay?

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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 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 $27 CAD per night before taxes and fees

  • Verified guest reviews

    Over 5,610 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    60 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

  • 4.7 Average rating

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

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  5. Cutler Bay