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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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
4.96 out of 5 average rating, 148 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
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, 250 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.

Top 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, 418 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 spacious pool area is surrounded by vibrant greenery and palm trees. Seating arrangements with cushions are positioned near the water, complemented by a shaded area under an umbrella. The pool features a rock formation and is accented by colorful lounge chairs.
Home in Miami
4.97 out of 5 average rating, 391 reviews

The Miracle Cottage & Pool on Acre Miami Florida

Beautiful, brand new PRIVATE cottage on an acre property situated in million dollar neighborhood. Perfect place to relax and enjoy the Miami sun. This is a little piece of heaven in the heart of a magical city. Come & enjoy your best vacation. Charming , peaceful & comfortable . Cottage is a completely separate building from the main house. It’s 900 sf of living area. Cleaning & Decontamination as per CDC guidelines before every check in.

Superhost
A private patio area features a large hot tub surrounded by white fencing and small plants. Soft lighting enhances the ambiance, while a decorative rug adds a touch of comfort beneath a wooden step. The space invites relaxation in a serene outdoor setting.
Guest suite in Miami
4.86 out of 5 average rating, 258 reviews

Miami Vibes -Large HOT TUB, Privacy, Clean

Comfortable 1 bedroom guest suite. Full bathroom with toiletries, full kitchen with amenities, walk-in closet. Perfect for up to 3 guests. Private entrance, private patio with large hot tub. Short distance from all of Miami's best attractions. Shopping malls, restaurants, nightclubs, bars/pubs, art centers, bicycle trails, beautiful parks, and bay views under 5-10 minutes away. Midpoint between Miami Beach 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
4.96 out of 5 average rating, 23 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
4.9 out of 5 average rating, 445 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.
Guesthouse 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
Guesthouse in Miami
4.87 out of 5 average rating, 135 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, 536 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.
Condo in Palmetto Bay
4.91 out of 5 average rating, 296 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
4.82 out of 5 average rating, 135 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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Avg. price$246 CAD$252 CAD$277 CAD$245 CAD$224 CAD$210 CAD$252 CAD$210 CAD$217 CAD$229 CAD$220 CAD$252 CAD
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Quick stats about vacation rentals in Cutler Bay

  • Total vacation rentals

    Explore 140 vacation rentals in Cutler Bay

  • Nightly prices starting at

    Cutler Bay vacation rentals start at $28 CAD per night before taxes and fees

  • Verified guest reviews

    Over 5,910 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 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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