Cutler Bay Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Cutler Bay vacation rentals

Living area
Art Gardens Wynwood

Art Gardens Wynwood

Art Gardens Wynwood
2.0 star property
Allapattah
7.2 out of 10, Good, (47)
"Loved it "
United States
Fidencio
The price is P4,083
P4,614 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Art Gardens Wynwood
Private kitchen
Kasa Collins Park Miami Beach Convention Center

Kasa Collins Park Miami Beach Convention Center

Kasa Collins Park Miami Beach Convention Center
2.0 star property
South Beach
8.4 out of 10, Very Good, (169)
"I will come back stay next year too!"
United States
Kanako
Kasa Collins Park Miami Beach Convention Center
Room amenity
Ocean Sand Inn

Ocean Sand Inn

Ocean Sand Inn
2.0 star property
South Beach
10.0 out of 10, Exceptional, (2)
"Amazing stay! The location is perfect—close to the beach and surrounded by great restaurants, which made everything so convenient. The price was excellent for the value, and the host was extremely helpful and responsive throughout our stay. Everything went smoothly from start to finish. I would definitely recommend this place to anyone—10/10!"
United States
Daniel
The price is P7,931
P10,804 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Ocean Sand Inn
Outdoor pool, free cabanas, pool umbrellas
Tradewinds Apartment Hotel

Tradewinds Apartment Hotel

Tradewinds Apartment Hotel
3.5 star property
South Beach
7.8 out of 10, Good, (2782)
"Nice room with nice price"
United States
Mo
The price is P4,183
P6,778 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Tradewinds Apartment Hotel
Outdoor pool, open 7:00 AM to 11:00 PM, sun loungers
Sentral Wynwood

Sentral Wynwood

Sentral Wynwood
4.0 star property
Wynwood Art District
9.2 out of 10, Wonderful, (1649)
"Great Stay!"
United States
Gregory
The price is P8,418
P11,507 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Sentral Wynwood
Lobby
Smart Brickell Hotel

Smart Brickell Hotel

Smart Brickell Hotel
4.0 star property
Brickell
8.6 out of 10, Excellent, (850)
"The room was very clean and the staff was very friendly."
United States
Clarence
The price is P5,241
P8,570 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Smart Brickell Hotel
Exterior
Stay Hospitality - Downtown Miami

Stay Hospitality - Downtown Miami

Stay Hospitality - Downtown Miami
2.0 star property
Downtown Miami
9.0 out of 10, Wonderful, (6)
"Beautiful "
United States
Felix
The price is P5,594
P21,337 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Stay Hospitality - Downtown Miami
Outdoor pool
Miami Vacation Rentals - Downtown

Miami Vacation Rentals - Downtown

Miami Vacation Rentals - Downtown
5.0 star property
Downtown Miami
9.2 out of 10, Wonderful, (40)
"Room was very nice, view was amazing, the only downside is the hotel is on a very busy corner there’s no running in to check in hotel parking is $70 "
United States
Jonathan
The price is P5,640
P27,010 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Miami Vacation Rentals - Downtown
Terrace/patio
Beautiful And Comfortable Home and studios

Beautiful And Comfortable Home and studios

Beautiful And Comfortable Home and studios
3.5 star property
Flagami
9.4 out of 10, Exceptional, (6)
"The house was super clean, had everything we needed for our trip. Really enjoyed the spacious rooms and amazing bathroom. Would definitely recommend for anyone who needs a great place to stay in a pinch "
United States
Gustavo
The price is P4,182
P14,673 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Beautiful And Comfortable Home and studios
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cutler Bay Hotel Reviews

Kompose Boutique Hotel Miami Airport

Kompose Boutique Hotel Miami Airport

10/10 Excellent
"Nice hotel , very clean "
Martha 3-night trip
Posted 12 hours ago
Kompose Boutique Hotel Miami Airport

Find out more about Cutler Bay

Search for holiday rentals in Cutler Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Cutler Bay using one of the methods below:

  • View our selection of featured holiday rentals in Cutler Bay
  • Use the map to find apartments and other holiday homes in the Cutler Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cutler Bay while they last

Look no further and take a look at our great range of rental properties in Cutler Bay!

Frequently asked questions

Can I find a vacation rental in Cutler Bay?

Yes, there are vacation rentals close to well known local attractions in Cutler Bay, or you can go with a more remote option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Cutler Bay. Make sure you have time to check out the coffeehouses and entertainment choices during your trip.

What are some of the best vacation home rentals that Cutler Bay has to offer?

Art Gardens Wynwood: Visitors like this Cutler Bay vacation home rental. It comes with free WiFi so you can feel at home during your trip. Amenities like a microwave and free parking are also available for your convenience.

How many vacation rentals will I find in Cutler Bay?

Choose from 39 Expedia vacation rentals in Cutler Bay for a memorable vacation.

What’s there to see and do in Cutler Bay?

Enjoy the area's cultural attractions such as Mal-Jonal Productions, or get outdoors into nature at a spot like Biscayne National Park. Other popular places to visit in the area include Dolphin Mall and Port of Miami.

What’s a vacation rental in Cutler Bay like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Cutler Bay. Vacation rentals feature extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for families.