Cutler Bay Vacations from $386

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Your Cutler Bay Vacation

With one of our vacation packages to Cutler Bay, you'll find infinite opportunities for fun and excitement. There's so much to enjoy, including its relaxed vibe and coastal scenery. Fill your itinerary with visits to Zoo Miami, Monkey Jungle and The Falls, some of the top attractions you really should see during a trip to Cutler Bay. Stop daydreaming and start doing. Browse the broad range of options on Expedia today and put your Cutler Bay vacation plans into gear!

The Latest Cutler Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was $799, price is now $386 per person
$386
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (814 reviews)
Good location, very walkable. Front desk staff is very nice.

Reviewed on Aug 8, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $23,583, price is now $11,011 per person
$11,011
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,134, price is now $540 per person
$540
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.

Reviewed on Aug 16, 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was $1,784, price is now $854 per person
$854
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (294 reviews)
We loved our stay at the Bentley Hotel! The staff was so friendly and always took the initiative to help us out. It was my girlfriend's birthday and when they learned aboit it they brought champagne, snacks to the room and left us a heartfelt card. Thank you again for your hospitality. We cannot wait to be back again!

Reviewed on Aug 24, 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was $983, price is now $494 per person
$494
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,414 reviews)
The property staff is perfect, the only sad thing is about the pool. But I want to came back very soon

Reviewed on Aug 25, 2025

Don't see what you're looking for?
See all available trips from Boydton to Cutler Bay
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Discover the most popular places to visit in Cutler Bay

Toured the Port of Miami with seven cruisers docked today. Currently the largest in the world, Symphony of Seas was preparing for its next excursion.

Port of Miami

Explore the waterfront in Miami Beach with a trip to Port of Miami. Amble around this vibrant area's beautiful beaches and enjoy its top-notch restaurants.

Port of Miami
Steelers and Dolphins

Hard Rock Stadium

Catch an event at Hard Rock Stadium during your trip to Miami Gardens. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Hard Rock Stadium
Ocean Drive

Ocean Drive

Miami’s famous strip is not only a gathering point for partiers but well worth the visit for lovers of 1920s art deco architecture.

Ocean Drive

What to do in Cutler Bay

Miami: 1-hour Jetcar Rental

Miami: 1-hour Jetcar Rental

$50
per traveler
Miami: 1-hour Jetcar Rental
Miami Skyline Evening Cruise on Biscayne Bay

Miami Skyline Evening Cruise of Biscayne Bay on luxury yacht

$23
per adult
Miami Skyline Evening Cruise of Biscayne Bay on luxury yacht
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

$27
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
See all activities in Cutler Bay

Cutler Bay Hotel Deals

Mondrian South Beach

Mondrian South Beach

4.5 out of 5
1100 West Ave, Miami Beach, FL
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $278 total per night from Aug 27 to Aug 28
$278 total
Aug 27 - Aug 28
Total with taxes and fees
7.8/10 Good! (2,376 reviews)
"Love the convenience of the hotel. Every where we go was very short and easy to get to."

Reviewed on Aug 25, 2025

Mondrian South Beach
citizenM Miami Worldcenter

citizenM Miami Worldcenter

4 out of 5
700 NE 2ND AVENUE, Miami, FL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Sep 7 to Sep 8
$101 total
Sep 7 - Sep 8
Total with taxes and fees
9.2/10 Wonderful! (5,048 reviews)
Technology at its finest
"Very convenient. It's right across Kaseya Center. The check in is self-service and very smooth. The room is modern with adequate amenities. Very clean and well-thought out. My kids had fun controlling the curtains and lights through the iPad. It was a great contrast to the previous place we stayed ..."

Reviewed on Aug 25, 2025

citizenM Miami Worldcenter
InterContinental Miami by IHG

InterContinental Miami by IHG

5 out of 5
100 Chopin Plz, Miami, FL
Fully refundable
$224 nightly
The price is $253 total per night from Sep 2 to Sep 3
$253 total
Sep 2 - Sep 3
Total with taxes and fees
9.2/10 Wonderful! (2,108 reviews)
Affordable luxury!
"Great hotel, fun location, really felt special!"

Reviewed on Aug 25, 2025

InterContinental Miami by IHG
See all 8,942 properties in Cutler Bay
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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Frequently asked questions

How much does a Cutler Bay vacation package cost?
You can snap up a vacation package to this destination from $386 on Expedia. But how much your vacation to Cutler Bay costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Cutler Bay?
You can generally find reduced prices and better availability in June, July and August. Take a look at our cheap Cutler Bay vacation packages and you could get some great off-season deals.
How many days is enough for Cutler Bay?
With a well-planned schedule, you can easily tick off the main Cutler Bay sights in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Cutler Bay vacation for longer.
How to find the best Cutler Bay package deals?
Landing a cheap Cutler Bay package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a few filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Cutler Bay package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Cutler Bay vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking accommodations and flights individually. Better still, you can customize your Cutler Bay escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Cutler Bay?
If you're planning an impromptu Cutler Bay trip, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Cutler Bay vacation packages?
Set off on your dream getaway to Cutler Bay with help from Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until your next payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.