Grassy Key Holidays from NZ$1,014

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The Latest Grassy Key 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
Save 100% on your flight
Price was NZ$1,889, price is now NZ$1,014 per person
NZ$1,014
per person
17 July - 20 July
found 10 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (1,830 reviews)
This hotel is very comfortable and welcoming, the service is excellent and the staff are very friendly. Highly recommended.

Reviewed on 7 May 2026

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 NZ$31,684, price is now NZ$15,424 per person
NZ$15,424
per person
17 July - 20 July
found 10 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8/10 Very Good! (1 review)
President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was NZ$2,068, price is now NZ$1,085 per person
NZ$1,085
per person
17 July - 20 July
found 10 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (2,302 reviews)
Location is 10/10. 1 minute walk to beach. Staff is amazing, super kind and helpful. Overall, a great stay. Highly recommend.

Reviewed on 7 May 2026

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Save 100% on your flight
Price was NZ$2,346, price is now NZ$1,359 per person
NZ$1,359
per person
17 July - 20 July
found 10 hours ago
Return flight included
New York (JFK) to Miami (MIA)
9.2/10 Wonderful! (464 reviews)
Loved the location in the middle of the art deco district. All staff were pleasant & helpful. Meals at restaurant were delicious.

Reviewed on 5 May 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Save 100% on your flight
Price was NZ$2,785, price is now NZ$1,642 per person
NZ$1,642
per person
17 July - 20 July
found 10 hours ago
Return flight included
New York (JFK) to Miami (MIA)
8/10 Very Good! (1,141 reviews)
Positives - Great food! Great amenities! Great section of the beach! Rooms were clean and modern! Negatives - Staff checking us in were not overly helpful - very transactional and seemed annoyed with any questions. - Beach had a lot of garbage - would be great if people would clean up after themselves, but if not, if there was staff to help pick up the garbage.

Reviewed on 4 May 2026

Grassy Key Holiday

Our pick of the best Grassy Key Hotel Deals

Rainbow Bend Resort

Rainbow Bend Resort

2.5 out of 5
57784 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
The price is NZ$253 per night from 14 May to 15 May
NZ$253
14 May - 15 May
includes taxes & fees
8.2/10 Very Good! (948 reviews)
Location was great, staff was professional and friendly, parking was good, room was clean.

Reviewed on 7 May 2026

Rainbow Bend Resort
Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club

4 out of 5
58182 Overseas Hwy Marathon FL
The price is NZ$576 per night from 8 June to 9 June
NZ$576
8 June - 9 June
includes taxes & fees
9.4/10 Exceptional! (441 reviews)
The room was outstanding. The view was absolutely gorgeous. We were on the same floor as the entertainment/bar, but the noise was minimal and stopped at a reasonable hour. Parking was convenient too. The staff on the front desk were always kind. The house cat, Wilma, is awesome. If there was any ...

Reviewed on 7 May 2026

Grassy Flats Resort & Beach Club
Gulf View Waterfront Resort

Gulf View Waterfront Resort

2.5 out of 5
58743 OVERSEAS HWY Marathon FL
The price is NZ$304 per night from 7 June to 8 June
NZ$304
7 June - 8 June
includes taxes & fees
8.4/10 Very Good! (570 reviews)
Nice landscaping and very quiet. Nice pool and water view. Usually in a hotel our dog barks at every thing. It was so quiet we actually slept all night.

Reviewed on 7 May 2026

Gulf View Waterfront Resort
See all 2,335 properties in Grassy Key
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 Grassy Key

Coco Plum Beach, Florida Keys

Coco Plum Beach

Why not spend a lazy afternoon at Coco Plum Beach during your trip to Marathon? Discover the area's beautiful sunsets or seek out its jogging trails.

Coco Plum Beach
Crane Point Museum and Nature Center

Crane Point Museum and Nature Center

You can spend an afternoon exploring the galleries in Crane Point Museum and Nature Center in Marathon. Discover the area's beautiful sunsets or seek out its jogging trails.

Crane Point Museum and Nature Center

What to do in Grassy Key

Marathon: Rhum Runner Aqua Park Adventure

Marathon: Rhum Runner Aqua Park Adventure

NZ$64
per adult
Marathon: Rhum Runner Aqua Park Adventure
Day Sailing Adventure in the Florida Marine Sanctuary

Day Sailing Adventure in the Florida Marine Sanctuary

NZ$203
per adult
100% of travellers recommend
Day Sailing Adventure in the Florida Marine Sanctuary
See all activities in Grassy Key

Frequently asked questions

Can I cancel my flight booking to Grassy Key due to COVID-19?
If you've yet to book your tickets, check the terms and conditions of the airfare you're considering. If you've already locked in your flight to Grassy Key, make use of our Customer Service Portal. It has information that will help you work out which COVID-19 policies apply to your reservation and provide you with the next steps.
What's the best way to find cheap flights to Grassy Key that have flexible change policies?
By using our nifty "No change fee" filter, that's how. Just type in your travel details, click "Search," then check the box underneath the "Flexible change policies" heading (to the left of your screen). Expedia makes it easy to find flexible and affordable tickets to Grassy Key.
What are some of the general tips for travellers to Grassy Key during the COVID-19 outbreak?
The COVID-19 pandemic has triggered substantial changes to the way we travel. If you're planning a trip to Grassy Key, these tips will help you navigate travel's newest challenges:
  • Investigate if any travel restrictions apply to your origin and destination before booking anything. Also check if there are any conditions you'll need to follow on arrival, such as proof of a negative COVID-19 test.
  • When you pass through airport screening, keep your face mask on. You will be required to lower it briefly to verify your identity. Anyone refusing to wear a mask may face civil penalties and may also be denied boarding.
  • Rather than handing a TSA employee your boarding pass, position it directly on the reader yourself. When that's done, hold it up for inspection.
  • You are now allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. This will need to be removed for X-ray scanning.
  • Remove items from your pockets, such as your wallet, coins and keys, and put them in your carry-on instead of the bins. This will reduce handling during the screening process.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA officer will need to open your bag for inspection.

Which airlines fly to Grassy Key?
Delta runs flights into or near Grassy Key, including 191 that land at Key West Intl. Airport (EYW) each month. Work out your holiday dates and then reserve your ticket early to score the best deal.
How can I find cheap tickets to Grassy Key?
For an amazing deal to Grassy Key, book well ahead of time. Also think about using Expedia's "flexible dates" feature above your search results. This will show you the cheapest prices for nearby days. In the last seven days, was the best price for a flight to Grassy Key.
How much is a flight to Grassy Key?
One-way flights taking off from () sold for just in the last seven days. During this time, the cost of a return ticket to Grassy Key ranged between and . If you spot a bargain ticket, book ASAP — these prices don't stick around for long.
What are the most popular airports to fly into in Grassy Key?
Pack your suitcase and fly into Key West Intl. Airport (EYW), Grassy Key's leading flight hub. Book a ticket on one of the 1119 flights that touch down at this favourite destination every month.
When is the cheapest time to fly to Grassy Key?
Try to leave earlier in the week to score the best deal to Grassy Key. Tuesday is usually the most affordable day to fly, with Monday a close second. Saturday often has the costliest ticket prices. This is because many travellers like to start their holiday on a weekend.
How much is a plane ticket to Grassy Key?
In the last seven days, plane fares to Grassy Key ranged from to .
Which airlines with flights to Grassy Key employ COVID-19 cleanliness policies?
In an effort to minimize contact between passengers and flight crew during the ongoing pandemic, many airlines have taken physical distancing and other strategies to the skies. A great example of these are:
  • 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.

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