Grassy Key Vacation Packages 2026 from $787

Grassy Key flight + hotel vacation packages

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

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$787

per person

May 7 - May 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.

Casablanca Miami Beach

North Beach

$3,685

per person

Jun 4 - Jun 11

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.

Creekside Inn

$932

per person

May 1 - May 8

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 Club Luxury Condos by Ilios Rentals

Brickell

Save 100% on your flight

$2,778

per person

Jun 19 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Miami (MIA)

An outdoor pool, valet parking, and laundry facilities are featured at this condo. There's a computer station and multilingual staff can provide around-the-clock assistance.

Top Grassy Key hotels deals

Rainbow Bend Resort

57784 Overseas Hwy Marathon FL

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$209 total

Apr 23 - Apr 24

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

$360 nightly

$405 total

Apr 30 - May 1

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.

Pool

Hot Tub

Gulf View Waterfront Resort

58743 OVERSEAS HWY Marathon FL

$215 nightly

$242 total

Apr 26 - Apr 27

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

The Nautilus on the Ocean in Grassy Key 4 bed 3 bath with private pool, Hot Tub and oceanfront, 2 kayaks included

Marathon FL

Get rates

An outdoor pool is featured at this vacation home, along with laundry facilities and barbecue grills.

Pool

Kitchen

Isla Bella Beach Resort & Spa

1 Knights Key Boulevard Marathon FL

Free Cancellation

Reserve now, pay when you stay

$417 nightly

$469 total

Apr 12 - Apr 13

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

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL

Free Cancellation

Reserve now, pay when you stay

$377 nightly

$423 total

Apr 26 - Apr 27

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

On private beach

Pool

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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(201 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(428 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(841 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 $787. 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.