Holiday rentals in Cutler Bay

4.96 out of 5 average rating, 148 reviews

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

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.

4.98 out of 5 average rating, 250 reviews

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

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.

4.91 out of 5 average rating, 418 reviews

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

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

4.97 out of 5 average rating, 391 reviews

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

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.

4.86 out of 5 average rating, 258 reviews

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

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.

4.9 out of 5 average rating, 447 reviews

Guest suite in Homestead

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. ✨ 💝

4.96 out of 5 average rating, 227 reviews

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

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.

4.87 out of 5 average rating, 137 reviews

Guest house in Miami

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.

4.83 out of 5 average rating, 536 reviews

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

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.

Apartment in Palmetto Bay

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.

4.91 out of 5 average rating, 297 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.

Guest house in Cutler Bay

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.

4.88 out of 5 average rating, 40 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.

Guest house in Cutler Bay

A compact sleeping area features a spacious bed with a light gray quilt and two pillows. Light wood beams stretch across the ceiling. A small wooden counter with a stool is positioned nearby, while storage cabinets are seen against the wall, providing functionality.

5 out of 5 average rating, 8 reviews

Cutler bay /Private entrance guest house

Convenience access / New construction Very clean and comfortable tiny house / fully equipped , stylish , small private patio , 2 min away from turnpike Very quiet place Private parking on property close to old cutler road historical area SMOKE / VIPING AND PET FREE ROOM

Popular amenities for Cutler Bay holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Cutler Bay

5 out of 5 average rating, 4 reviews

Home in Homestead

Everglades-Homestead. Tropical Retreat. Miami-Keys

Guest house in Florida City

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.

4.99 out of 5 average rating, 99 reviews

Luxury Loft

4.75 out of 5 average rating, 32 reviews

A modern kitchen area features sleek white cabinetry and a stainless steel microwave. Natural light filters in through an open door, illuminating the countertop and tiled floor. A small trash bin is positioned beside the cabinetry, complementing the clean, minimalist look.

Home in Homestead

Apartment with 1 bedroom

Campervan/Motorhome in Homestead

An RV is positioned on a gravel surface, showcasing its sleek exterior design. Surrounding greenery includes palm trees, adding to the outdoor ambiance. A privacy fence lines the property, providing a sense of seclusion, while a residential structure is visible in the background.

4.97 out of 5 average rating, 31 reviews

Nomadic Nook! RV Nights!

5 out of 5 average rating, 6 reviews

A serene studio space is showcased, featuring a spacious bed with white bedding. A small television is positioned against the wall, and a sleek dresser stands nearby. A door opens to an outdoor area, and a mirror reflects the soft light in the room.

Flat in Miami

Cozy studio in West Kendall

4.96 out of 5 average rating, 23 reviews

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

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

4.98 out of 5 average rating, 52 reviews

A spacious sleeping area is furnished with a king-size bed and a smaller twin bed, both adorned with coordinated bedding. Two bedside tables with lamps flank the larger bed. A soft area rug in geometric patterns adds color to the light-colored tiled floor.

Flat in Homestead

Private Entry Cozy Room/Bath Homestead/Florida key