Cutler Bay Holidays

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  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Top hotels in Cutler Bay

Hyatt Regency Miami

Hyatt Regency Miami

4 out of 5
400 Se 2nd Ave Miami FL
The price is S$269 per night from 23 Nov to 24 Nov
S$269
23 Nov - 24 Nov
includes taxes & fees
8.8/10 Excellent! (2,818 reviews)
"Amazing staff and clean rooms. Lovely stay"

Reviewed on 27 Oct, 2026

Hyatt Regency Miami
Kompose Boutique Hotel Miami Airport

Kompose Boutique Hotel Miami Airport

3 out of 5
3401 NW 25th St Miami FL
The price is S$139 per night from 2 Nov to 3 Nov
S$139
2 Nov - 3 Nov
includes taxes & fees
Kompose Boutique Hotel Miami Airport
Loews Miami Beach Hotel – South Beach

Loews Miami Beach Hotel – South Beach

4.5 out of 5
1601 Collins Ave Miami Beach FL
Fully refundableReserve now, pay when you stay
The price is S$510 per night from 30 Oct to 31 Oct
S$510
30 Oct - 31 Oct
includes taxes & fees
Loews Miami Beach Hotel – South Beach
See all 10,604 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.

Stay near popular Cutler Bay attractions

Regal Southland Mall

This 16-screen theatre offers comfortable stadium seating and the latest blockbusters within Southland Mall. Combine your film experience with shopping and dining options for a complete entertainment outing.
See properties

What to do in Cutler Bay

12 hours Day at Key West With Boat Tour and Snorkeling

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

S$42
per adult
82% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

S$42
per adult
Full Day Trip in Key West from Miami
Bimini Bahamas Day Cruise!!

Bahamas Day Cruise with Hotel Pickup

S$316
per adult
82% of travellers recommend
Bahamas Day Cruise with Hotel Pickup
See all activities in Cutler Bay

Frequently asked questions

How much does a Cutler Bay holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday 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?
If you'd like to book a cheap Cutler Bay holiday package, consider travelling in June, August and September. You'll generally find lower prices on flights and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Cutler Bay?
With a well-organised itinerary, you can easily tick off the most popular Cutler Bay attractions in a few days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Cutler Bay holiday 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 personalise 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking accommodation and flights individually. Better still, you can customise 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 holiday 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.
How to plan a trip to Cutler Bay?

  1. Choose your dates: The things you'd like to do in Cutler Bay and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in expenses such as flights, transportation and food when calculating how much to set aside for your trip to Cutler Bay. Then, choose a hotel that suits your budget, whether that's an affordable option or a more upscale retreat.
  3. Set the duration of your trip: Start by listing all the activities and attractions you'd like to experience in Cutler Bay. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Cutler Bay holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.