Grassy Key Holidays from NZ$2,741

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The Latest Grassy Key Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was NZ$3,830, price is now NZ$2,741 per person
NZ$2,741
per person
24 Aug - 31 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
The staff were all helpful the building itself was incredible the food was beyond excellent the only bad thing was the valet service so if you stay please park your own car

Reviewed on 22 June 2026

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
Price was NZ$7,643, price is now NZ$4,991 per person
NZ$4,991
per person
24 Aug - 31 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
9.4/10 Exceptional! (1,558 reviews)
My favorite hotel in South Beach. The design of this hotel never gets old, the restaurants are great! The staff amazing. I will come back every time I get a chance.

Reviewed on 22 June 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Price was NZ$4,584, price is now NZ$3,261 per person
NZ$3,261
per person
24 Aug - 31 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8.4/10 Very good! (8,366 reviews)
I’ve been coming to Fountainebleu for years and have to say this one probably the most disappointed I’ve ever been. Tons of construction (which I realize they can’t help), but all of the little touches that I’ve come to love about FB were gone. Limited water stations, no change to the pool menu, and they are even getting rid of their signature scent. Just bummed out.

Reviewed on 22 June 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was NZ$4,374, price is now NZ$3,181 per person
NZ$3,181
per person
24 Aug - 31 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
8/10 Very good! (1,154 reviews)
Lo que no me gustó fue el trato en el restaurante, por política de alimentos en el desayuno, ya que no podia terminarme un cereal que además lo empacaron en plástico y pensé en llevármelo para comerlo luego en el cuarto y me hicieron botarlo junto con el de mi esposa, el trato fue desagradable, un momento feo y que me hizo no cenar en el hotel, no ver más partidos del mundial y no consumir más cerveza en su bar, realmente me sentí decepcionado de una política sin sentido, prefieren botar la comida a que luego te la puedas comer. Espero, que cambien de manera de pensar…

Reviewed on 21 June 2026

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was NZ$4,875, price is now NZ$3,574 per person
NZ$3,574
per person
24 Aug - 31 Aug
found 21 hours ago
Return flight included
Auckland (AKL) to Miami (MIA)
9.4/10 Exceptional! (917 reviews)
Large rooms, friendly staff

Reviewed on 21 June 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$262 per night from 28 June to 29 June
NZ$262
28 June - 29 June
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"This is a beautiful older hotel which has been updated. Rooms were large, clean and tastefully furnished. The staff were friendly and very accommodating. The free breakfast was provided by the restaurant (Hideaway Cafe) on site. I had delicious lemon ricotta pancakes with a side of sausage for breakfast. ..."

Reviewed on 16 June 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$434 per night from 23 June to 24 June
NZ$434
23 June - 24 June
includes taxes & fees
9.4/10 Exceptional! (460 reviews)
"When we arrived we were greeted by Mia. Such a nice young lady and very helpful! We had dinner at The Rhum House and the food and service was fantastic! Our room was very clean and spacious. We were disappointed by the beach but came to find out that is common in the Keys. Also liked how the resort ..."

Reviewed on 17 June 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$316 per night from 23 June to 24 June
NZ$316
23 June - 24 June
includes taxes & fees
8.4/10 Very good! (587 reviews)
"Did not get to stay at the accommodation due to the host never providing the “contactless” check in code as they indicated they would. I responded to their text that they stated we could communicate through in case of issues but they never communicated with us on what to do through that text platform. ..."

Reviewed on 18 June 2026

Gulf View Waterfront Resort
See all 2,377 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$204
per adult
100% of travellers recommend
Day Sailing Adventure in the Florida Marine Sanctuary
Sister snorkelers :)

Marathon: COMBO- Snorkel & Sandbar (Sombrero Reef)

NZ$262
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.