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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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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, 175 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
An outdoor patio area features comfortable seating arrangements under a shaded pergola, overlooking a large swimming pool. The vibrant green lawn is bordered by palm trees, while the sunset colors softly illuminate the sky in the background.
Villa in Miami
4.89 out of 5 average rating, 181 reviews

NEW! "Villa Paradise" ~ Luxury Gem ~ Pool ~ Game Room

Bring your family to the luxurious 3BR 2Bath Villa Paradise in the tranquil and friendly neighborhood in southern Miami, FL. Visit the exciting attractions, natural landmarks, restaurants, shops, and much more, and then retreat to the lavish oasis that will leave you in awe with its stylish design, private backyard, and rich amenity list. ✔ 3 Comfortable BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Heated Pool ✔ Game Room ✔ Smart TVs ✔ Smart House ✔ High-Speed Wi-Fi ✔ Free Parking

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, 138 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, 270 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
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.

Top guest favourite
Villa in Cutler Bay
4.96 out of 5 average rating, 47 reviews

Waterfront Miami Villa | Pool, Kayaks, Mini Golf

Escape to this stunning waterfront villa, perfect for families and groups up to 11. Set along a peaceful canal, this private retreat blends relaxation and adventure with direct water access and resort-style amenities. Resort-Style Highlights: • Heated private pool • Complimentary kayaks & life jackets • Mini golf & outdoor lounging • Smart TVs, fast WiFi, and modern interiors Minutes from Black Point Marina, Miami, and the Florida Keys.

Guest favourite
A pool area is featured, surrounded by lush greenery and palm trees. Sun loungers are positioned next to the inviting pool, with a shaded seating area under an umbrella visible in the background. The structure has large glass doors that provide access to the interior.
Home in Cutler Bay
4.92 out of 5 average rating, 37 reviews

4BR Home with Pool, Playground & Boat/RV Parking

Beautiful Cutler Bay pool home with large backyard, boat/rv parking, and playground. Whether you're planning a getaway to the Florida Keys, soaking up the sun on the beaches of Miami, or just looking for a cozy staycation, this home is your perfect launchpad for everything South Florida has to offer. • The Florida Keys – 48 minutes • Miami Beach – 37 minutes • Everglades National Park – 33 minutes

Superhost
Home in Cutler Bay
4.87 out of 5 average rating, 216 reviews

Miami Relax Oasis: w/ Heated Pool_Spa & Basketball

Heated pool/Jacuzzi/Basketball court/5B Indulge in luxury for a relaxing vacation, basking in Miami's warm weather. Revel in our spacious heated pool and Jacuzzi adorned with umbrellas, loungers, and snack tables. Each room is tastefully decorated with meticulous care. Sports enthusiasts will adore our basketball court. Perfect for your family and friends, our space awaits.

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.
Guest house in Miami
4.96 out of 5 average rating, 240 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
An inviting pool area features clear blue water surrounded by a privacy fence and lush greenery. Sunlight reflects off the pool’s surface, creating a serene outdoor space ideal for relaxation and enjoyment.
Home in Princeton
4.87 out of 5 average rating, 112 reviews

Tropical Paradise Between Miami and the FL Keys

Located within a quiet and desirable neighborhood is this stunning ultra-modern home offering unparalleled style and design across 2 levels of luxury living. The house features a living room, a kitchen, 3 luxurious bedrooms, an incredible games room and glamorous outdoor living with a swimming pool and outdoor dining and an incredible children's play place.

Guest favourite
Guest house in Miami
4.85 out of 5 average rating, 173 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.
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.

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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