Florida Keys Holidays from NZ$2,272

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The Latest Florida Keys Holiday Deals

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

The Penguin Hotel

3.5 out of 5
South Beach
Price was NZ$2,748, price is now NZ$2,272 per person
NZ$2,272
per person
19 Oct - 25 Oct
found 6 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.2/10 Very Good! (1,432 reviews)
Really great price and location.

Reviewed on 15 Sept 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was NZ$3,815, price is now NZ$2,707 per person
NZ$2,707
per person
19 Oct - 25 Oct
found 6 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.2/10 Very Good! (961 reviews)
Honestly, it’s the best place we have ever stayed on Ocean Drive! The boardwalk is across the street. About a 20 minute walk to South Pointe. Our room was spacious. Very comfortable, clean and modern. Bathroom could use a cabinet or shelves to store toiletries. Balcony facing the ocean was our favorite for people watching. We will definitely return and ask for the same room!!

Reviewed on 17 Sept 2025

Club Wyndham Palm-Aire

Club Wyndham Palm-Aire

3 out of 5
Price was NZ$2,895, price is now NZ$2,429 per person
NZ$2,429
per person
19 Oct - 25 Oct
found 6 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Our room was awesome! We were upgraded to a 2 bedroom and 2 bath which was very spacious. Rooms were very clean. We didn’t get time to enjoy the pool or arcade area - but did view it and it looked very nice, clean and spacious area. Would definitely go back if in that area again.

Reviewed on 15 Sept 2025

Hyatt Regency Miami

Hyatt Regency Miami

4 out of 5
Downtown Miami
Price was NZ$3,361, price is now NZ$2,872 per person
NZ$2,872
per person
19 Oct - 25 Oct
found 6 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.8/10 Excellent! (1,956 reviews)
Great, I’ll be back next year

Reviewed on 17 Sept 2025

Esmé Miami Beach

Esmé Miami Beach

4 out of 5
South Beach
Price was NZ$2,809, price is now NZ$2,423 per person
NZ$2,423
per person
19 Oct - 25 Oct
found 6 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
9/10 Wonderful! (1,306 reviews)
Such a great place to stay! At the center of everything, with lots of great food options and very near the beach.

Reviewed on 17 Sept 2025

Our guide on where to stay in Florida Keys

Find the best Florida Keys areas and neighborhoods for the activities you enjoy most. Learn more about Florida Keys
Default Image

Old Town Key West

3 out of top 10 points of interest in this area

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Saint Mary Star of the Sea.

Find hotels in Old Town Key West

Florida Keys Holiday

Our pick of the best Florida Keys Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$336 per night from 21 Sept to 22 Sept
NZ$336
21 Sept - 22 Sept
includes taxes & fees
9/10 Wonderful! (1,198 reviews)
Very Nice Resort and AMAZING STAFF!
"Honestly, we started with a pretty bad experience with some issues pertaining to our room. However, we mentioned it to Natalia at the concierge and she was SUPER accommodating! Needless to say that the issues were resolved immediately. Definitely recommend Cheeca Lodge & Spa to anyone looking for ..."

Reviewed on 16 Sept 2025

Cheeca Lodge & Spa
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd, Marathon, FL
Fully refundableReserve now, pay when you stay
The price is NZ$598 per night from 28 Sept to 29 Sept
NZ$598
28 Sept - 29 Sept
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"Had an amazing and relaxed time with my family! Dolphin encounter was so much fun and educational. I do recommend having a microwave in rooms. Thank you for the amazing hospitality 🙏"

Reviewed on 15 Sept 2025

Hawks Cay Resort
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4 out of 5
97000 Overseas Hwy, Key Largo, FL
Fully refundableReserve now, pay when you stay
The price is NZ$522 per night from 25 Sept to 26 Sept
NZ$522
25 Sept - 26 Sept
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"The beach it’s one of the best places in the keys,"

Reviewed on 16 Sept 2025

Baker's Cay Resort Key Largo, Curio Collection by Hilton
See all 8,335 properties in Florida Keys
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.

Discover the most popular places to visit in Florida Keys

Duval Street

Duval Street

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Duval Street
Southernmost Point

Southernmost Point

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
Mallory Square

Mallory Square

Enjoy the lively crowds, energetic performers and stunning sunset that make this city square the most popular meeting place in the evenings.

Mallory Square

What to do in Florida Keys

12 hours Day at Key West With Boat Tour and Snorkeling

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

NZ$46
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

NZ$85
per adult
92% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

NZ$46
per adult
Full Day Trip in Key West from Miami
See all activities in Florida Keys

Frequently asked questions

Can I cancel my flight booking to Florida Keys due to COVID-19?
If you've yet to book your tickets, read the terms and conditions of the airfare you're considering. If you've already reserved your flight to Florida Keys, make use of our Customer Service Portal. The information here will help determine which COVID-19 policies apply to your booking and guide you with the next steps.
What's the best way to find cheap flights to Florida Keys that have flexible change policies?
We understand that things can change from one minute to the next, so booking a flexible ticket with Expedia is a sensible idea. Just tick the "No change fee" box directly under the "Flexible change policies" filter. Your low-cost, flexible flight to Florida Keys is just a few clicks away.
What are some of the general tips for travellers to Florida Keys during the COVID-19 outbreak?
The COVID-19 pandemic has brought about dramatic changes to the way we travel. If you're planning an escape to Florida Keys, the following tips will help you navigate these new rules and challenges:
  • Research what, if any, rules or restrictions apply to both your origin and destination. It may not be possible to travel depending on local circumstances, so be sure to check before you lock something in.
  • When you pass through airport screening, keep your face mask on. You will be asked to briefly lower it for identification purposes. Anyone refusing to wear a mask may be fined and denied entry.
  • Avoid handing your boarding pass directly to a TSA employee. Instead, position the pass on the reader and then hold it up to allow the agent to visually inspect it.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag for screening.
  • Put any personal items (phone, wallet and keys) in your carry-on rather than a bin to minimize handling during screening.
  • Separate any food you have for X-ray screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Florida Keys?
Delta is a leading airline servicing Florida Keys. Search for airfares to Key West Intl. Airport (EYW) and you'll have 191 Delta flights each month to pick from.
How can I find cheap tickets to Florida Keys?
An effective strategy for scoring cheap airfares is to be flexible with your travel dates. Begin with searching for your flight to Florida Keys, then click on the "flexible dates" box to see prices for nearby days. Another helpful hint? Book well in advance. To give you an idea of fares, was the best price for a flight to Florida Keys in the last seven days.
How much is a flight to Florida Keys?
The cost of a round-trip journey to Florida Keys in the last seven days ranged between and . If you were travelling one way from (), you could have gotten a great deal from only .
What are the most popular airports to fly into in Florida Keys?
Start planning your Florida Keys escape by securing one of the 1119 flights each month to Key West Intl. Airport (EYW). This is the region's main entry point.
When is the cheapest time to fly to Florida Keys?
Jet off on a Tuesday to boost your odds of picking up the cheapest deal to Florida Keys. Mondays are usually the second most affordable day to depart. Saturday is normally the most expensive day to fly anywhere.
How much is a plane ticket to Florida Keys?
In the last seven days, ticket prices to Florida Keys varied from to .
Which airlines with flights to Florida Keys employ COVID-19 cleanliness policies?
As passengers begin travelling once again, most reputable airlines have introduced social distancing and other important measures to help lessen the spread of COVID-19. Here are some of them:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • Frontier Airlines - this airline is known for electrostatic cleaning and conducting passenger temperature checks.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.