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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Cutler Bay holiday rentals

Beach
Residence at the Four Seasons

Condo in Brickell

Residence at the Four Seasons
3.5 star property
10.0 out of 10, Exceptional, (3)
"Spacious, incredible amenities. "
United States
Ana
The price is ฿4,028
฿17,682 total
includes taxes & fees
18 Dec - 19 Dec
Residence at the Four Seasons
2 outdoor pools, free pool cabanas, pool umbrellas
Premier Condos Key Biscayne Getaway

Aparthotel in Key Biscayne

Premier Condos Key Biscayne Getaway
4.0 star property
9.4 out of 10, Exceptional, (3)
"If you’d like to stay at the Ritz and enjoy the amenities at a discount this is a great option. You will certainly be paying enough at the hotel restaurants on top of parking and the resort fee so it’s great to save money on the room. It’s a great option for the price but just be aware the room could use a deep cleaning. The main issues were the bathtub drain is clearly blocked and drains slowly, the bathroom vent is disgusting and full of dust and the floor wiped up brown when we had a spill so...
United States
Laura
The price is ฿22,715
฿38,145 total
includes taxes & fees
24 Dec - 25 Dec
Premier Condos Key Biscayne Getaway
Outdoor pool
Miami Vacation Rentals - Coconut Grove

Aparthotel in Coconut Grove

Miami Vacation Rentals - Coconut Grove
3.5 star property
8.8 out of 10, Excellent, (512)
"Easy check in & check out, great communication! Wonderful location "
United States
Madeleine
The price is ฿3,372
฿7,908 total
includes taxes & fees
22 Dec - 23 Dec
Miami Vacation Rentals - Coconut Grove
Living area
Ocean Sand Inn

Aparthotel in South Beach

Ocean Sand Inn
2.0 star property
10.0 out of 10, Exceptional, (1)
"Fabulous mattress, place was clean and bright with darkening shades. Amazing view. On the beach close to all restaurants. Oh kitchen had literally everything from wine opener to lobster or crab cracking plier things"
Canada
Jackson
The price is ฿4,259
฿5,802 total
includes taxes & fees
17 Dec - 18 Dec
Ocean Sand Inn
Panoramic Apartment, 3 Bedrooms, Kitchen, City View | Interior
17WEST Apartments by Stay Hospitality

17WEST Apartments by Stay Hospitality

17WEST Apartments by Stay Hospitality
3.5 star property
9.2 out of 10, Wonderful, (217)
"Download the Sonder app, it'll make your stay way easier. Very nice apartment but little details missing like a door handle, the app kept crashing when trying to report it. Nice coffee and so conveniently located"
United States
JOSE
The price is ฿7,193
฿14,298 total
includes taxes & fees
22 Dec - 23 Dec
17WEST Apartments by Stay Hospitality
2 outdoor pools, open 7:00 AM to 7:00 PM, pool umbrellas, pool loungers
Suites at SLS LUX Brickell managed by CE

Aparthotel in Brickell

Suites at SLS LUX Brickell managed by CE
5.0 star property
9.8 out of 10, Exceptional, (69)
"Great room with great location. David was extremely helpful."
Australia
Daniel
The price is ฿6,171
฿13,274 total
includes taxes & fees
17 Dec - 18 Dec
Suites at SLS LUX Brickell managed by CE
Outdoor pool
Stylish Apartments with Partial Ocean Views in Downtown

Apartment in Downtown Miami

Stylish Apartments with Partial Ocean Views in Downtown
3.5 star property
10.0 out of 10, Exceptional, (2)
"Beautiful apartment, we loved "
United States
Elba
The price is ฿5,131
฿11,169 total
includes taxes & fees
17 Dec - 18 Dec
Stylish Apartments with Partial Ocean Views in Downtown
Presidential Corner Apart, 2 Bedrooms, Frontal Ocean Views2510 | Egyptian cotton sheets, premium bedding, in-room safe
Miami Vacation Rentals - Brickell

Apartment in Brickell

Miami Vacation Rentals - Brickell
4.0 star property
8.8 out of 10, Excellent, (547)
"This is our second stay at this property. Looking forward to coming again"
Canada
Masood
The price is ฿3,825
฿11,389 total
includes taxes & fees
21 Dec - 22 Dec
Miami Vacation Rentals - Brickell
Studio Terrace | Terrace/patio
Blanc Kara - Adults Only

Aparthotel in South Beach

Blanc Kara - Adults Only
3.5 star property
9.0 out of 10, Wonderful, (1696)
"Rudolfo and Alex are very helpful and friendly, do recommend"
United States
Liutsiia
Blanc Kara - Adults Only
Outdoor pool
AKA Brickell 32th Free Parking by Palermo Home

Apartment in Brickell

AKA Brickell 32th Free Parking by Palermo Home
3.0 star property
10.0 out of 10, Exceptional, (3)
"This was an absolutely stunning place to stay! High end accommodations connected to the AKA hotel. Close to the water, great restaurant, the pool was fabulous. Easy to get around to everything in Miami from here. Parking included with this reservation, which was a huge plus. Highly recommend this for anyone staying in Miami whether for a couple or a family of four."
United States
Kris
The price is ฿8,216
฿14,265 total
includes taxes & fees
22 Dec - 23 Dec
AKA Brickell 32th Free Parking by Palermo Home
Family House, 3 Bedrooms, Ground Floor | Terrace/patio
Amazing & cozy Duplex near Zoo Miami

Holiday Home in South Miami Heights

Amazing & cozy Duplex near Zoo Miami
3.5 star property
10.0 out of 10, Exceptional, (2)
"Foi tudo perfeito!"
Brazil
SILVIO
The price is ฿4,533
฿10,992 total
includes taxes & fees
14 Jan - 15 Jan 2026
Amazing & cozy Duplex near Zoo Miami
Classic Studio, 1 King Bed, Non Smoking (Elser 2705) | Exterior
Stay Hospitality - Downtown Miami

Aparthotel in Downtown Miami

Stay Hospitality - Downtown Miami
2.0 star property
8.8 out of 10, Excellent, (5)
"Beautiful "
United States
Felix
The price is ฿3,673
฿12,201 total
includes taxes & fees
17 Dec - 18 Dec
Stay Hospitality - Downtown Miami
Apartment | 2 bedrooms
Luxury Sobe 2 Bedroom Apartment

Aparthotel in South Beach

Luxury Sobe 2 Bedroom Apartment
2.0 star property
8.0 out of 10, Very good, (1)
"The property is exactly as pictured. The condo is conveniently located within walking distance of the beach, Ocean Drive, grocery store, and shopping/dining. The unit is off the main street just enough where it is quiet. I used Expedia to book this unit. All communications afterwards came through a third party email travelstation or guesty. You are also required to do an online check in, again this is through another third party website. Upon arriving, security is an issue. The main front...
United States
Charles
The price is ฿6,379
฿14,962 total
includes taxes & fees
17 Dec - 18 Dec
Luxury Sobe 2 Bedroom Apartment
2 Bedroom w/ Balcony | Private kitchen | Fridge, microwave, stovetop, dishwasher
Roami at Habitat Brickell

Apartment in Brickell

Roami at Habitat Brickell
4.0 star property
8.8 out of 10, Excellent, (341)
"The environment was very clean and the staff were very friendly "
Canada
TEMITOPE
The price is ฿3,237
฿7,009 total
includes taxes & fees
18 Dec - 19 Dec
Roami at Habitat Brickell
Interior
Unique Escape GameRoom! Bar, BBQ, Spacious, and Near Beach

Residence in Coral Way

Unique Escape GameRoom! Bar, BBQ, Spacious, and Near Beach
4.5 star property
10.0 out of 10, Exceptional, (2)
"Family of 10 for birthday celebration, ages from 1 to 51 this house had something for everyone. Backyard setup is next level and beds are very comfortable. Highly recommended."
United States
Edwin
The price is ฿7,451
฿23,688 total
includes taxes & fees
17 Dec - 18 Dec
Unique Escape GameRoom! Bar, BBQ, Spacious, and Near Beach
Comfort Condo, 2 Bedrooms | Living area | 50-inch Smart TV with cable channels
Miami Apt Close to Downtown

Apartment in Midtown

Miami Apt Close to Downtown
3.0 star property
10.0 out of 10, Exceptional, (6)
"Excellent apartment great to stay. I will stay again in the future host was very attentive. five stars. Close to everything location is perfect."
United States
Daniel
The price is ฿2,392
฿8,217 total
includes taxes & fees
17 Dec - 18 Dec
Miami Apt Close to Downtown
Condo, 3 Bedrooms, Balcony, City View | City view
Modern Condos Located in Brickell

Apartment in Brickell

Modern Condos Located in Brickell
3.0 star property
10.0 out of 10, Exceptional, (7)
"Love the view!"
United States
Malgorzata
The price is ฿3,211
฿10,814 total
includes taxes & fees
17 Dec - 18 Dec
Modern Condos Located in Brickell
Exterior
Port Miami

Aparthotel in Downtown Miami

Port Miami
4.5 star property
10.0 out of 10, Exceptional, (1)
Port Miami
Design Apartment | Living room | 42-inch LCD TV with cable channels
Milla South Beach

Apartment in South Beach

Milla South Beach
4.0 star property
7.2 out of 10, Good, (11)
"Very nice place highly recommend for families. Good location, too. "
United States
Monika
Milla South Beach
Lobby sitting area
Baybreeze Apartments by Lowkl

Apartment in South Beach

Baybreeze Apartments by Lowkl
2.5 star property
8.0 out of 10, Very good, (236)
"Temperature control easily accessible. Room very clea and kit hen well stocked. Not very spacious. Neighborhood easily walkable."
United States
Brenda
The price is ฿3,691
฿4,208 total
includes taxes & fees
23 Dec - 24 Dec
Baybreeze Apartments by Lowkl
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.
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Top Cutler Bay Hotel Reviews

Loews Miami Beach Hotel – South Beach

Loews Miami Beach Hotel – South Beach

10/10 Excellent
"It was my birthday and they brought me a free charcuterie board to my room, the entire property is so beautiful, loved the easy access to the beach, the food at the restaurants was great, and my room was cleaned daily! Loved everything 🙂"
Godlyse 3-night trip
Posted 1 day ago
Loews Miami Beach Hotel – South Beach

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 holiday rental in Cutler Bay?

Yes, there are holiday rentals close to the most popular sights in Cutler Bay, or you can select a more secluded 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 coffee shops and entertainment choices during your trip.

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

Art Gardens Wynwood: This holiday home rental outside of Cutler Bay comes with free WiFi so that you can feel at home during your trip. Amenities such as a microwave and free parking are also available for your convenience.

How many holiday rentals will I find in Cutler Bay?

Choose from 40 Expedia holiday rentals in Cutler Bay for a memorable holiday.

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

Enjoy the area's cultural attractions such as Bayfront Park, 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 holiday rental in Cutler Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cutler Bay. Holiday rentals feature extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for small groups.