Cutler Bay Vacation Rentals

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Our top choices for Cutler Bay vacation rentals

Welcome to Casa Luna – Your Private Oasis with a Heated Pool!

Welcome to Casa Luna – Your Private Oasis with a Heated Pool!
Cutler Bay
9.8 out of 10, Exceptional, (8)
"Property was beautiful and safe, very clean and Elizabeth was communicative and kind."
United States
Marti M.
$701 nightly
The price is $783
Jan 12 - Jan 13, 2026
Total with taxes and fees
Welcome to Casa Luna – Your Private Oasis with a Heated Pool!

3-BR Stay in Cutler Bay w/ Fast Wi-Fi, AC, Smart Lock & Parking –Pets,near Keys

3-BR Stay in Cutler Bay w/ Fast Wi-Fi, AC, Smart Lock & Parking –Pets,near Keys
2.0 star property
Cutler Bay
$325 nightly
The price is $363
Jan 5 - Jan 6, 2026
Total with taxes and fees
3-BR Stay in Cutler Bay w/ Fast Wi-Fi, AC, Smart Lock & Parking –Pets,near Keys

Secluded Bungalow Oasis & Sanctuary garden between Miami & Keys

Secluded Bungalow Oasis & Sanctuary garden between Miami & Keys
Cutler Bay
7.8 out of 10, Good, (14)
"Easy check in, very nice host"
United States
Alex S.
$120 nightly
The price is $133
Jan 4 - Jan 5, 2026
Total with taxes and fees
Secluded Bungalow Oasis & Sanctuary garden between Miami & Keys

Villa Elena - Private Pool

Villa Elena - Private Pool
Cutler Bay
10.0 out of 10, Exceptional, (12)
"The house was gorgeous!! Relaxing and welcoming upon arrival. I would definitely recommend this home! Pool was large and warm :). "
United States
Jaydine H.
$902 nightly
The price is $1,006
Dec 26 - Dec 27
Total with taxes and fees
Villa Elena - Private Pool

Private Villa • Pool & Waterfall

Private Villa • Pool & Waterfall
Cutler Bay
10.0 out of 10, Exceptional, (4)
"Truly a fantastic residence! Owners were responsive and extremely helpful. We will be back! "
United States
Lauren N.
$1,142 nightly
The price is $1,274
Dec 26 - Dec 27
Total with taxes and fees
Private Villa • Pool & Waterfall

Beautiful Miami Pool Lake Studio

Beautiful Miami Pool Lake Studio
Cutler Bay
8.4 out of 10, Very Good, (25)
"Awesome "
United States
Rob R.
$178 nightly
The price is $199
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Miami Pool Lake Studio

Spacious Miami House/5 mins from Marina/Ocean/Pool/Tennis

Spacious Miami House/5 mins from Marina/Ocean/Pool/Tennis
Cutler Bay
8.6 out of 10, Excellent, (28)
"Stay was enjoyable for the family. Beds were comfortable. "
United States
Carla H.
$474 nightly
The price is $531
Jan 3 - Jan 4, 2026
Total with taxes and fees
Spacious Miami House/5 mins from Marina/Ocean/Pool/Tennis

Good Vibes Oasis, 2 Story Townhome in Cutler Bay

Good Vibes Oasis, 2 Story Townhome in Cutler Bay
Cutler Bay
8.0 out of 10, Very Good, (1)
"Nice spot with everything you need. Our host was very responsive. The property was clean and comfortable. Would recommend!!!"
United States
Cheryl W.
$489 nightly
The price is $543
Dec 30 - Dec 31
Total with taxes and fees
Good Vibes Oasis, 2 Story Townhome in Cutler Bay

Family Retreat Sleeps 11, Heated Pool, Mini Golf, Kayak Experience, Waterfront

Family Retreat Sleeps 11, Heated Pool, Mini Golf, Kayak Experience, Waterfront
2.0 star property
Cutler Bay
10.0 out of 10, Exceptional, (10)
"This was the perfect rental for our family of 5. The home was spacious and comfortable, and we loved being able to spend time in the pool, each evening. "
United States
Ami C.
$1,196 nightly
The price is $1,334
Dec 31 - Jan 1, 2026
Total with taxes and fees
Family Retreat Sleeps 11, Heated Pool, Mini Golf, Kayak Experience, Waterfront

Hidden Garden, Miami Escape, Parking and Spacious

Hidden Garden, Miami Escape, Parking and Spacious
Cutler Bay
6.0 out of 10, (3)
"The bed was comfortable, the air worked great, the shower water was hot, and the backyars was a great place to hang out in the mornings and evenings. Great location for going to Miami, the everglades or the upper keys."
United States
April P.
$470 nightly
The price is $518
Jan 8 - Jan 9, 2026
Total with taxes and fees
Hidden Garden, Miami Escape, Parking and Spacious

Sentral Wynwood

Sentral Wynwood
4.0 star property
Wynwood Art District
9.2 out of 10, Wonderful, (1637)
"Great Stay!"
United States
Gregory
$174 nightly
The price is $196
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sentral Wynwood

Tradewinds Apartment Hotel

Tradewinds Apartment Hotel
3.5 star property
South Beach
7.8 out of 10, Good, (2777)
"Nice room with nice price"
United States
Mo
$109 nightly
The price is $124
Jan 7 - Jan 8, 2026
Total with taxes and fees
Tradewinds Apartment Hotel

Art Gardens Wynwood

Art Gardens Wynwood
2.0 star property
Allapattah
7.0 out of 10, Good, (46)
"Loved it "
United States
Fidencio
$53 nightly
The price is $60
Dec 28 - Dec 29
Total with taxes and fees
Art Gardens Wynwood

Nine20 Collins Apartments by Lowkl

Nine20 Collins Apartments by Lowkl
3.0 star property
South Beach
8.0 out of 10, Very Good, (743)
"Great stay!"
United States
Jessie
$108 nightly
The price is $123
Jan 5 - Jan 6, 2026
Total with taxes and fees
Nine20 Collins Apartments by Lowkl

Baybreeze Apartments by Lowkl

Baybreeze Apartments by Lowkl
2.5 star property
South Beach
8.0 out of 10, Very Good, (237)
"Temperature control easily accessible. Room very clea and kit hen well stocked. Not very spacious. Neighborhood easily walkable."
United States
Brenda
$113 nightly
The price is $128
Jan 6 - Jan 7, 2026
Total with taxes and fees
Baybreeze Apartments by Lowkl

Blanc Kara - Adults Only

Blanc Kara - Adults Only
3.5 star property
South Beach
9.0 out of 10, Wonderful, (1699)
"Great stay would stay again"
United States
Moneisha
$175 nightly
The price is $199
Jan 6 - Jan 7, 2026
Total with taxes and fees
Blanc Kara - Adults Only

Smart Brickell Hotel

Smart Brickell Hotel
4.0 star property
Brickell
8.6 out of 10, Excellent, (839)
"The room was very clean and the staff was very friendly."
United States
Clarence
$170 nightly
The price is $192
Jan 5 - Jan 6, 2026
Total with taxes and fees
Smart Brickell Hotel

Aloha Fridays

Aloha Fridays
3.0 star property
South Beach
8.6 out of 10, Excellent, (68)
"It was clean and close to everywhere "
United States
Elif
$224 nightly
The price is $255
Dec 25 - Dec 26
Total with taxes and fees
Aloha Fridays

Miami Vacation Rentals - Coconut Grove

Miami Vacation Rentals - Coconut Grove
3.5 star property
Coconut Grove
8.8 out of 10, Excellent, (514)
"Easy check in & check out, great communication! Wonderful location "
United States
Madeleine
$267 nightly
The price is $302
Jan 4 - Jan 5, 2026
Total with taxes and fees
Miami Vacation Rentals - Coconut Grove

1818 Meridian House Apartments and Suites by Eskape Collection

1818 Meridian House Apartments and Suites by Eskape Collection
3.0 star property
South Beach
8.0 out of 10, Very Good, (667)
"Comfortable Room in great location"
United States
Jeff
$147 nightly
The price is $168
Jan 20 - Jan 21, 2026
Total with taxes and fees
1818 Meridian House Apartments and Suites by Eskape Collection
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

Find out more about Cutler Bay

Everything you need to know about Cutler Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cutler Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cutler Bay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cutler Bay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cutler Bay. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cutler Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $123 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cutler Bay rentals

At Expedia, we put the best Cutler Bay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cutler Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cutler Bay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cutler Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.