Holiday rentals in Cutler Bay

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Top-rated holiday rentals in Cutler Bay

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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, 171 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 rooftop pool area is showcased, featuring a shimmering blue pool surrounded by orange lounge chairs. A white umbrella provides shade to one section. In the background, expansive views of the bay and a clear blue sky are visible, enhancing the serene atmosphere.
Flat in Coconut Grove
4.9 out of 5 average rating, 223 reviews

Stunning Studio w/Bay & City View Free Park/Pool

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 deluxe bright studio on the 15th floor of a luxurious waterfront property offers breathtaking bay & city views, is equipped for 2 guests w/king size bed, full kitchen, full bath & balcony. Enjoy all the luxury amenities we offer, pool & hot-tub w/ incredible bay views, penthouse gym, sauna, business center, squash.

Guest favourite
A bright guest room features large arched windows with sheer curtains allowing soft light to illuminate the space. A spacious bed with light bedding is centered in the room, complemented by a wooden table and a chair. A ceiling fan is visible above.
Guest suite in Coral Way
4.89 out of 5 average rating, 242 reviews

Quiet Guest Suite, Private Entrance, Patio+Parking

Take it easy at this unique and tranquil getaway in our 1930's Spanish Villa in the center of Little Havana and Coral Gables in the heart of Shenandoah. Your Guest Suite is equipped with a private entrance, private garden, and parking. Casita Amorcita is designed to give you the feeling of 'home' and 'love,' with the guest experience in mind. All linens are 100% cotton. Here you will have all that you need to rest, recover, recharge, and enjoy. We look forward to welcoming you home.

Top guest favourite
A spacious outdoor area features a heated pool surrounded by lounge chairs and potted plants. A colorful children's playground is set on lush green grass, creating an inviting space for relaxation and play. The backdrop showcases a well-maintained villa under a bright, sunny sky.
Home in Miami
4.97 out of 5 average rating, 105 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
A crystal-clear pool is surrounded by well-maintained greenery and modern high-rise buildings. Sun loungers line one side, and a shaded seating area is visible in the background. The tranquil water reflects the blue sky, creating a serene atmosphere for relaxation.
Flat in Brickell
4.95 out of 5 average rating, 244 reviews

Condo in Brickell Business District

Stunning one bedroom condo located in the best area of Brickell just minutes away from Brickell City Centre and Mary Brickell Village with restaurants, bars, shops and entertainment. About this Space -Approx.818 sqft of natural light filled space with gorgeous bay and city views and a large private balcony with dining table and large patio couch -High-speed Wi-Fi -1 free assigned parking spot -Pool, hot tub, jacuzzi, steam room, game room, state of the art gym, and business center

Guest favourite
The entrance of the property is framed by mature palm trees and lush landscaping, showcasing vibrant greenery. A large half-circle driveway leads up to the house, highlighted by a smooth, paved surface. The warm-toned exterior of the home is visible, inviting guests into a tranquil setting.
Guest suite in Miami
4.91 out of 5 average rating, 431 reviews

Cozy Suite -Exterior Entrance, SelfCheckin

If you like Clean, New, Quiet and Great Hospitality, then this is the Perfect Room 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 -Bathroom with 2 sinks -SWIMMING POOL -Central A/C -HBO TV -Refrigerator -Ceiling Fan -Closet Space -Ceramic Tile Floors -Iron & Board -Towels & Bath essentials -Hair dryer

Guest favourite
A spacious lawn features a large shade tree with swings hanging from its branches. Nearby are colorful chairs arranged on the grass, along with a hammock tied between tree trunks. Water is visible in the background, surrounded by lush greenery.
Guest suite in Cutler Bay
4.78 out of 5 average rating, 307 reviews

Private Waterfront Studio Paradise

Casa Cocos is a private studio, with a private entrance, bathroom and kitchenette, and free and secure parking. It is nestled in Florida's tropical waterfront paradise. Come enjoy the views of the garden, go for a swim, paddle board, canoe, kayak, grill, take a nap in a hammock, and just relax. Casa Cocos is surrounded by nearby restaurants, bars, retail stores, malls all within walking distance or a short drive. 30 minutes to airport, downtown, South Beach, Keys, and Everglades.

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, 135 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 home in Cutler Bay
4.97 out of 5 average rating, 265 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.

Guest favourite
A modern two-story residence is shown, featuring a neutral façade of light and dark materials. Large windows are visible on the upper level, and a sleek garage door is positioned on the right. A minimalist landscape design includes young trees and a scooter parked on the driveway.
Guest house in Florida City
4.98 out of 5 average rating, 119 reviews

Luxury Loft

Kick back and relax in this calm, stylish space. A private suite with your own entrance, your personal parking space and no shared space with others! Safe neighborhood close to the Florida Keys, Outlet mall, Miami, the Everglades and so much more. Equipped with all the essential to make your stay comfortable. Just 3 minutes away from Walmart, 25 minute drive to the Keys & 27 to Miami! Nearby Everglades (5 min ) Key Largo (30 min) Miami (20 min) Hospital ( 10 min)

Top guest favourite
Guest suite in Homestead
4.99 out of 5 average rating, 179 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
Guest house in Miami
4.96 out of 5 average rating, 237 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.

Popular amenities for Cutler Bay holiday 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 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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  2. United States
  3. Florida
  4. Miami-Dade County
  5. Cutler Bay