Grassy Key Holidays from NZ$3,512

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The Latest Grassy Key Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Landon Bay Harbor - Miami Beach

The Landon Bay Harbor - Miami Beach

3.5 out of 5
Price was NZ$4,638, price is now NZ$3,512 per person
NZ$3,512
per person
30 Apr - 5 May
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.2/10 Very Good! (1,003 reviews)
The room was very clean and a comfortable homey feel

Reviewed on 16 Mar 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was NZ$25,115, price is now NZ$15,440 per person
NZ$15,440
per person
30 Apr - 5 May
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
9.4/10 Exceptional! (1,464 reviews)
This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again!

Reviewed on 7 Mar 2026

Andaz Miami Beach Resort & Spa

Andaz Miami Beach Resort & Spa

5 out of 5
Mid Beach
Save 100% on your flight
Price was NZ$14,766, price is now NZ$9,176 per person
NZ$9,176
per person
30 Apr - 5 May
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
9.4/10 Exceptional! (198 reviews)
Housekeeping was inconsistent. Didnt clean our room 1 day. My husband and I paid for 3 rooms for our family and they gave one of our children a huge suite and we had a tiny room with very small bathroom. They wouldn’t move us.

Reviewed on 22 Mar 2026

JW Marriott Turnberry Resort & Spa

JW Marriott Turnberry Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was NZ$13,086, price is now NZ$9,010 per person
NZ$9,010
per person
30 Apr - 5 May
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.6/10 Excellent! (1,500 reviews)
Fantastic! Best Hotel I ever stayed at.

Reviewed on 12 Mar 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was NZ$5,871, price is now NZ$4,196 per person
NZ$4,196
per person
30 Apr - 5 May
found 1 day ago
Return flight included
Auckland (AKL) to Miami (MIA)
8/10 Very Good! (1,165 reviews)
Check in was easy, staff really friendly, room was clean. Gym has good equipment. Great breakfast. Pool heated, warm. Lot of sun beds on the beach. Easy to transport to the North and South Beach and Ocean drive. We liked the hotel position, the food, the ocean view from our balcony.

Reviewed on 22 Mar 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$374 per night from 19 Apr to 20 Apr
NZ$374
19 Apr - 20 Apr
includes taxes & fees
8.2/10 Very Good! (892 reviews)
Small resort with its own private beach. Beach loungers are available but there are only eight of them. Onsite restaurant but we never ate there. Older property but in reasonably good shape. The rooms could have been cleaner. The floors did not look dirty but our socks were filthy after just a short ...

Reviewed on 22 Mar 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$618 per night from 21 Apr to 22 Apr
NZ$618
21 Apr - 22 Apr
includes taxes & fees
9.4/10 Exceptional! (419 reviews)
Relaxed location on the keys, not too busy and plenty of restaurants nearby and on location to have a different experience each night. Resort had friendly and helpful staff with plenty of activities on site to take advantage of. 2 beautiful pool areas, beach area with various activities available ...

Reviewed on 19 Mar 2026

Grassy Flats Resort & Beach Club
Gulf View Waterfront Resort

Gulf View Waterfront Resort

2.5 out of 5
58743 OVERSEAS HWY Marathon FL
8.4/10 Very Good! (562 reviews)
It is a cute little place to stay. We enjoyed the pool, outdoor games and relaxed on the little beach area

Reviewed on 19 Mar 2026

Get rates
Gulf View Waterfront Resort
See all 2,289 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 featuring general coastal views

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$63
per adult
Marathon: Rhum Runner Aqua Park Adventure
Our sailboat is named Chao Lay. The boat has completed one complete circumnavigation of the globe crossing the Atlantic, Pacific, and Indian Oceans.

Day Sailing Adventure in the Florida Marine Sanctuary

NZ$200
per adult
100% of travellers recommend
Day Sailing Adventure in the Florida Marine Sanctuary
Sister snorkelers :)

Marathon: COMBO- Snorkel & Sandbar (Sombrero Reef)

NZ$257
per adult
Marathon: COMBO- Snorkel & Sandbar (Sombrero Reef)
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.