Holiday rentals in Cutler Bay

4.97 out of 5 average rating, 132 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.

4.99 out of 5 average rating, 148 reviews

Villa in Homestead

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.

4.93 out of 5 average rating, 132 reviews

Tiny home in Cutler Bay

Cozy Treehouse in Private Garden, Pool

Read entire listing for FAQ Contact AIRBNB for changes to your reservation We welcome all! Come reconnect with yourself and nature in this Zen garden. Surrounded by love, peace, nature in peaceful surroundings Located between Miami Beach & The Keys Beautiful & Quiet Residential Area South of Miami Close to all major roads. *this is a treehouse, so it is a small space, FULL SIZE bed (54 x 75 inches). Private bathroom adjacent to treehouse. Look at our other listings in main house.

4.97 out of 5 average rating, 235 reviews

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.

4.96 out of 5 average rating, 26 reviews

Canal front, 2 King Beds, Pool, Game Room

Indulge in a luxurious family-friendly retreat at our newly remodeled, high-end home featuring a stunning pool and canal views. This spacious 4-bedroom home is perfect for your entire family. Located on a tranquil canal, our home offers a serene ambiance with a small dock where you can unwind. Inside, you'll find a fully equipped kitchen, pool table, and multiple smart TVs. 2 king, 1 queen bed plus futon provides plenty of space. Centrally located 45m to either Miami Beach or Key Largo.

4.91 out of 5 average rating, 407 reviews

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

4.98 out of 5 average rating, 47 reviews

Flat in Homestead

Private Entry Cozy Room/Bath Homestead/Florida key

Come stay at this elegant and peaceful get away. Have your own private entrance, private bathroom, king size bed in this spacious, updated suite. It is located minutes away from Black Point Marina, Knaus Berry Farm, pharmacies, shopping centers, supermarkets, and plenty more. This place is also near the Everglades, Homestead Speedway, Schelby's Winery, and Florida Keys. Your home away from home. **Additional cleaning fees apply to guests who stay longer than 14 days**

Superhost

4.96 out of 5 average rating, 181 reviews

Miami Oasis: Heated Pool, Spa & Basketball

Heated pool/Jacuzzi/Basketball court/5BR 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.

Superhost

Guest suite in Miami

4.83 out of 5 average rating, 518 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.

Apartment in Palmetto Bay

4.91 out of 5 average rating, 281 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

4.84 out of 5 average rating, 31 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.

4.92 out of 5 average rating, 225 reviews

Guest suite in Homestead

Cozy 1BR guestroom, private entrance, free parking

This is a 1 bed 1 bath with queen bed, controllable AC, and private entrance. WiFi and Netflix included. Ideal for planning a quick trip to the keys or the Everglades. Florida Keys Outlet shops and Knauss Berry Farm are just a few minutes drive!

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Other great holiday rentals in Cutler Bay

4.9 out of 5 average rating, 51 reviews

Home in Palmetto Bay

Paradise in Palmetto Bay with Pool~BBQ~Gazebo

KcRating, 5 stars1 week ago

We loved our stay at Mikes! He was so friendly and accommodating! The pool area was beautiful.

4.89 out of 5 average rating, 38 reviews

Spacious 3BR Cutler Bay Home

BrendaRating, 5 stars1 month ago

My family and I really enjoyed to stay there. I would highly recommend if a person is looking for somewhere that's clean that's quiet even the person who you call when anything is needed. They're always available at any time.

5 out of 5 average rating, 17 reviews

Home in Miami

Escape to Miami/Heather+Pool/9pl/BBQ/pool table

KristinaRating, 5 stars1 week ago

Perfect!! From the beginning to the end of our stay, Enrique was quick to respond, kind, considerate and accommodating. The home itself was beautiful and in perfect condition for us. The pool and surroundings were as good as it gets. Relaxing with shade or sun and grilling to top it off. It was truly an amazing stay and we hope to book again soon. 10 out of 10 ⭐️ Thank you

5 out of 5 average rating, 8 reviews

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

MeredithRating, 5 stars1 week ago

Holly's home is absolutely gorgeous, I was in awe of the backyard. It is magical! This was the perfect getaway for us and I will 100% stay with her again. The house is so well equipped, clean, and feels so cozy. I highly recommend her place.

Home in Palmetto Bay

5 out of 5 average rating, 4 reviews

Beautiful Vacation Home

Johana PRating, 5 stars2 weeks ago

We really had a wonderful time with my family and I fully recommend this house Everyone enjoyed both pool and the play areas in the house. Just the 4th room had the laundry and a/c in the room. Overall, the house was spectacular, and everyone was amazed by it.

4.93 out of 5 average rating, 40 reviews

Flat in Miami

Purple Haven | Top Location | BBQ| Parking | Patio

PillyRating, 5 stars5 days ago

Loved the privacy of this place and how clean it and spacious it was. Would definitely come back!

4.95 out of 5 average rating, 43 reviews

Villa in Cutler Bay

Waterfront Miami Resort : Pool, Spa, Kayaks & more

EmmaRating, 5 stars1 week ago

One of the BEST air bnbs i’ve stayed in!!! Super clean and fun place to stay in. Andres couldn’t have been more nice and helpful. Definitely recommend!