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, 157 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
4.98 out of 5 average rating, 254 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. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

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, 421 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

Top 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
4.99 out of 5 average rating, 102 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)

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
4.96 out of 5 average rating, 26 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

Guest favourite
Guest suite in Homestead
4.89 out of 5 average rating, 449 reviews

Tranquil Retreat with Vintage Charm

🌴 Retreat to a private guest suite in one of the area’s safest communities, just north of Key Largo. With a plush bed, upscale amenities, and a Smart TV, you’ll enjoy boutique comfort in a prime location—minutes from Everglades and Biscayne National Parks, and a short drive to Miami or the Florida Keys. Perfect for travelers who want both style and convenience. ✨ 💝

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, 227 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
Guest house in Miami
4.87 out of 5 average rating, 141 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.

Superhost
A cozy sleeping area features a spacious bed covered with a light quilt. Soft lighting is provided by two bedside lamps on turquoise tables. A large framed artwork of a serene ocean scene hangs above the bed, complemented by a stylish black and white patterned closet door.
Guest suite in Miami
4.83 out of 5 average rating, 539 reviews

Private 1bd/1bath guest suite.

We are a great location for day trips to Key Largo and the rest of the Keys as well as the Everglades. Cozy 1 bedroom studio apartment with a private entrance, bathroom, and kitchen. It is located in a very quiet area of Cutler Bay, between Key Largo and Downtown Miami. This space is perfect for travelers that prefer a peaceful retreat.

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
4.91 out of 5 average rating, 299 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, 138 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 🙂

Guest favourite
A studio apartment features a spacious bed with soft linens and a ceiling fan for comfort. A dining area with a table and chairs is positioned beside a compact kitchen that includes a refrigerator and microwave. A wardrobe is visible, providing storage options.
Guest house in Cutler Bay
4.88 out of 5 average rating, 41 reviews

Studio Private Entry close to Blackpoint Marina

Welcome to our cozy and convenient short-term rental studio apartment, where comfort meets functionality in every square foot. Nestled in a serene neighborhood, this charming abode offers a retreat-like ambiance perfect for solo travelers or couples seeking a home away from home.

Popular amenities for Cutler Bay holiday rentals

When is the best time to visit Cutler Bay?

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Avg. price$229 SGD$234 SGD$257 SGD$227 SGD$208 SGD$195 SGD$230 SGD$195 SGD$195 SGD$212 SGD$204 SGD$234 SGD
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Frequently Asked Questions

  • Are there pet-friendly house rentals in Cutler Bay?

    Four-legged friends are welcome in Cutler Bay. Choose from more than 40 house rentals for guests traveling with pets.

  • Are there family-friendly house rentals in Cutler Bay?

    Cutler Bay has more than 60 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Cutler Bay have wifi?

    Absolutely! We offer over 90 house rentals with wifi in Cutler Bay. Enjoy a tailored experience with all the comforts you desire.

  • Are there house rentals with a dedicated workspace in Cutler Bay?

    Yes! Work meets play with ease at over 50 house rentals in Cutler Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Cutler Bay have air conditioning?

    Absolutely! We offer over 90 house rentals with air conditioning in Cutler Bay. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Cutler Bay?

    Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with wifi, over 80 homes with a kitchen, over 90 homes with air conditioning, over 90 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in house rentals in Cutler Bay?

    Experience the best of Cutler Bay with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Cutler Bay house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Cutler Bay, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Cutler Bay have a kitchen?

    Absolutely! We offer over 80 house rentals with a kitchen in Cutler Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cutler Bay have free parking?

    Absolutely! We offer over 90 house rentals with free parking in Cutler Bay. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Cutler Bay

  • Total holiday rentals

    Explore 140 holiday rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,910 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 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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