Grassy Key Vacation Packages 2026 from $339

Grassy Key flight + hotel vacation packages

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

Bay Breeze Premium Apartments By Eskape Collection

$339

per person

Feb 28 - Mar 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This aparthotel features an outdoor pool and a rooftop terrace. WiFi in public areas is free. Self parking, a garden, and luggage storage are also offered.

Creekside Inn

$568

per person

Jan 30 - Feb 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.

The Shelborne By Proper, a Member of Design Hotels

South Beach

$1,247

per person

Feb 27 - Mar 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Hawks Cay Resort

$1,030

per person

Mar 17 - Mar 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

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. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$6,938

per person

Mar 5 - Mar 8

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

This condo resort 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.

Top Grassy Key hotels deals

Rainbow Bend Resort

57784 Overseas Hwy Marathon FL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$172 total

Jan 4 - Jan 5, 2026

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.

On private beach

Pool

Grassy Flats Resort & Beach Club

58182 Overseas Hwy Marathon FL

$391 nightly

$440 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

This smoke-free hotel features 2 outdoor pools, a restaurant, and a bar/lounge. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. Concierge services are provided for your convenience.

Pool

Pet friendly

Gulf View Waterfront Resort

58743 OVERSEAS HWY Marathon FL

$179 nightly

$201 total

Jan 6 - Jan 7, 2026

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.

Pool

Pet friendly

Beachfront Explorer!

Marathon FL

Get rates

Enjoy laundry facilities and air conditioning. Popular attractions Keys Cable Park and Crawl Key are located nearby.

Pet friendly

Air conditioning

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL

Free Cancellation

Reserve now, pay when you stay

$310 nightly

$348 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

On private beach

Pool

Isla Bella Beach Resort & Spa

1 Knights Key Boulevard Marathon FL

Free Cancellation

Reserve now, pay when you stay

$407 nightly

$458 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

This smoke-free hotel features a full-service spa, 5 outdoor pools, and a restaurant. Spend a day at the beach scuba diving, or relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Spa

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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.

Popular places to visit

Dolphin Research Center

4.5/5(194 reviews)

Learn about the playful nature of dolphins before swimming alongside these clever marine mammals at this entertaining research facility.

Sombrero Beach

4.5/5(417 reviews)

Play beach games; go swimming, kayaking or snorkeling; and lounge in the sun at one of Marathon’s most visited beaches.

Seven Mile Bridge

4.5/5(830 reviews)

Walk, jog, cycle or drive across one of the longest bridges in North America to take in the scenic ocean views it provides.

Frequently asked questions

How much are vacation packages to Grassy Key?

Your vacation dreams can come to life in Grassy Key from just $339. 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.