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The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was $1,076, price is now $514 per person
$514
per person
Nov 5 - Nov 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. WiFi in public areas is free. Valet parking, a terrace, and a garden are also offered.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

4 out of 5
Old Town Key West
Price was $2,891, price is now $958 per person
$958
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a terrace, and a picnic area are also offered.
Pantera Rosa

Pantera Rosa

4 out of 5
South Beach
Price was $1,314, price is now $572 per person
$572
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This aparthotel features valet parking and free WiFi in public areas. Express check-in and express check-out are also provided.
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 $12,418, price is now $6,026 per person
$6,026
per person
Oct 23 - Oct 26
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This aparthotel features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
Sea Glass Cove

Sea Glass Cove

3.5 out of 5
Price was $5,571, price is now $2,724 per person
$2,724
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
A private beach and an outdoor pool are featured at this vacation home. Relax with free beach cabanas, sun loungers, and beach umbrellas. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

Top Grassy Key hotels deals

Rainbow Bend Resort

Rainbow Bend Resort

2.5 out of 5
57784 Overseas Hwy Marathon FL
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $158 total per night
$158 total
Sep 8 - Sep 9
Total with taxes and fees
A private beach and an outdoor pool are featured at this hotel. A hot tub, a restaurant, and a garden are also provided.
Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club

4 out of 5
58182 Overseas Hwy Marathon FL
$184 nightly
The price is $207 total per night
$207 total
Aug 25 - Aug 26
Total with taxes and fees
This smoke-free hotel features 2 outdoor pools, a hot tub, and a restaurant. Enjoy the sauna and perks like free self parking and free WiFi. There's a bar/lounge on site, and concierge services and barbecue grills are also provided.
Gulf View Waterfront Resort

Gulf View Waterfront Resort

2.5 out of 5
58743 OVERSEAS HWY Marathon FL
$68 nightly
The price is $77 total per night
$77 total
Aug 25 - Aug 26
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. There's an outdoor pool on site, and laundry facilities and barbecue grills are also offered.
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard Marathon FL
Free Cancellation
Reserve now, pay when you stay
$262 nightly
The price is $294 total per night
$294 total
Aug 19 - Aug 20
Total with taxes and fees
This smoke-free hotel features a full-service spa, 5 outdoor pools, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Make the most of the gym and steam room, and relax with drinks at one of the 2 bars/lounges.
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd Marathon FL
Free Cancellation
Reserve now, pay when you stay
$264 nightly
The price is $295 total per night
$295 total
Aug 24 - Aug 25
Total with taxes and fees
This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with kayaking.
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy Long Key FL
Free Cancellation
Reserve now, pay when you stay
$172 nightly
The price is $194 total per night
$194 total
Aug 23 - Aug 24
Total with taxes and fees
This resort features a private beach, 3 outdoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the outdoor tennis court and perks like free self parking.
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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.

Frequently asked questions

How much are vacation packages to Grassy Key?
Your vacation dreams can come to life in Grassy Key from just $514. Vacation packages include flights and hotels, and they'll make your booking nice and easy. All you'll have to focus on is having a good time.
How long should my Grassy Key vacation be?
Most people reserve their hotel for 3 nights in Grassy Key. But that doesn't mean you have to follow in their footsteps. How long you hang around comes down to how much you want to see during your vacation. If your aim is to familiarize yourself with every square inch of this impressive place, consider booking another night or so (or even longer!).
Where can I get the best vacation package deals for Grassy Key?
You can snap up sensational Grassy Key package deals with Travelocity. Mix and match from 400 partner airlines and 1,000,000 properties worldwide and turn those vacation daydreams into reality.
Why should I purchase my Grassy Key vacation package via Travelocity?
Because you'll never roam on your own if you secure your trip with us, and we offer 24/7 customer support and top-notch service to boot. Add to that our Price Match Guarantee and a huge range of destinations to select from. We're here to make your daydreams a reality.
Can I save on my Grassy Key car rental if I combine it with a hotel or flight?
Certainly — bundle your car, flight and hotel into a Grassy Key vacation package and you'll save a handsome sum. With so much to see and do in Grassy Key, having your own set of wheels will make exploring a joy. Once you've slid into the driver's seat, crank up the tunes and make your way to PortMiami, an unmissable attraction roughly 85 mi from Grassy Key.
What is the best time of year to go to Grassy Key?
Pack your bags in and you can spend more cash on awesome experiences, not your hotel room. This is the most inexpensive month to book a stay. Prices are at their most expensive in , so avoid traveling during this time if you're on a tight budget. January, February and September are the tourist season months in Grassy Key. You'll need to book ahead of time and be prepared to pay more. August, October and November are the quietest months.
Which airport is best for Grassy Key?
The main airport is Key West Intl. Airport (EYW). Grab your bags, step out of the terminal and you'll discover yourself 50 mi from downtown Grassy Key.
Where should I stay when visiting Grassy Key?
If you're searching for a place to lay your head, check out the Gulf View Waterfront Resort. It's the top choice for many travelers.

Photos of local treasures

Browse Grassy Key vacation photos for more inspiration

A dolphin swimming near a wooden dock and a tree branch in the water.
A beach with clear turquoise water, surrounded by lush green trees and a distant shoreline with buildings.
A calm bay with clear turquoise water, surrounded by lush green vegetation and a sandy beach.
A building with a blue awning labeled "Dolphin Research Center" and a dolphin logo.
A dolphin sculpture and a sign for the Dolphin Research Center.

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