Grassy Key Vacation Packages for 2025

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Grassy Key Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Stay at this 4-star beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Las Olas Beach and Port Everglades are located nearby.

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Stay at this 4-star luxury hotel in Fort Lauderdale. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fort Lauderdale Beach and Las Olas Beach are located nearby.

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Akron (CAK) to Key West (EYW)
Stay at this 3.5-star eco-certified hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

The Seagate

The Seagate

4.5 out of 5
Downtown Delray Beach
Save 100% on your flight
per person
Sep 14 - Sep 20
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Stay at this 4.5-star luxury hotel in Delray Beach. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Atlantic Avenue and Veterans Park are located nearby.

The Ray Hotel Delray Beach, Curio Collection by Hilton

The Ray Hotel Delray Beach, Curio Collection by Hilton

4 out of 5
Downtown Delray Beach
Save 100% on your flight
per person
Sep 14 - Sep 20
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Stay at this 4-star beach hotel in Delray Beach. Enjoy free WiFi, 2 restaurants, and a free beach shuttle. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Atlantic Avenue and Puppetry Arts Center of the Palm Beaches are located nearby.

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Akron (CAK) to Key West (EYW)
Stay at this 3.5-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

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Top Hotel Deals

Rainbow Bend Resort

Rainbow Bend Resort

2.5 out of 5
57784 Overseas Hwy, Marathon, FL
0.92 km from city center
Book a stay at this beach hotel in Marathon. Enjoy a private beach, daily housekeeping, and a garden. Our guests praise the breakfast and the helpful staff in ...
Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club

2.5 out of 5
58182 Overseas Hwy, Marathon, FL
0.37 km from city center
Book a stay at this beach hotel in Marathon. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...
Gulf View Waterfront Resort

Gulf View Waterfront Resort

2.5 out of 5
58743 OVERSEAS HWY, Marathon, FL
0.57 km from city center
Stay at this hotel in Marathon. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd, Marathon, FL
4.54 km from city center
Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard, MM 47, Marathon, FL
17.99 km from city center
Stay at this 5-star luxury hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

2.5 out of 5
13201 Overseas Hwy, Marathon, FL
7.54 km from city center
Book a stay at this business-friendly hotel in Marathon. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the restaurant ...
Lime Tree Bay Resort

Lime Tree Bay Resort

3.5 out of 5
68500 Overseas Hwy, Long Key, FL
15.42 km from city center
Stay at this 3.5-star beach resort in Long Key. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

4 out of 5
1996 Overseas Highway, Marathon, FL
16.43 km from city center
Stay at this 4-star beach resort in Marathon. Enjoy free WiFi, 2 outdoor pools, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
Courtyard by Marriott Faro Blanco Resort

Courtyard by Marriott Faro Blanco Resort

3 out of 5
2146 Overseas Hwy, Marathon, FL
16.31 km from city center
Stay at this 3-star beach hotel in Marathon. Enjoy free WiFi, 2 outdoor pools, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. ...
Tranquility Bay Beachfront Hotel and Resort

Tranquility Bay Beachfront Hotel and Resort

4 out of 5
2600 Overseas Hwy, Marathon, FL
15.99 km from city center
Stay at this 4-star beach hotel in Marathon. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Coconut Cay Resort & Marina

Coconut Cay Resort & Marina

2 out of 5
7196 Overseas Highway, Marathon, FL
12.14 km from city center
Stay at this hotel in Marathon. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Yacht Haven Marina

Yacht Haven Marina

3.5 out of 5
5 Sombrero Blvd, Marathon, FL
13.66 km from city center
Stay at this 3.5-star houseboat in Marathon. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hampton Inn Marathon - Florida Keys

Hampton Inn Marathon - Florida Keys

2.5 out of 5
13351 Overseas Highway, Marathon, FL
7.33 km from city center
Book a stay at this business-friendly hotel in Marathon. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool ...
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
61 Hawks Cay Boulevard, Villas, Marathon, FL
4.55 km from city center
Stay at this 4-star luxury resort in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Popular attractions Little Conch Key and Walkers Island ...
Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway

3 out of 5
1480 Overseas Hwy, Marathon, FL
16.84 km from city center
Stay at this 3-star hotel in Marathon. Enjoy free WiFi, a marina, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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See all available properties in Grassy Key
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Oct 20 - Mon, Nov 3
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$70 Roundtrip, found 5 days ago
$70
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Mon, Nov 3, priced at $70 found 5 days ago
Spirit Airlines
Mon, Nov 17 - Thu, Nov 27
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$89 Roundtrip, found 3 days ago
$89
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Nov 17 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Thu, Nov 27, priced at $89 found 3 days ago
Delta
Tue, Oct 28 - Tue, Nov 4
BOS
Logan Intl.
MIA
Miami Intl.
$117 Roundtrip, found 23 hours ago
$117
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Oct 28 from Logan Intl. to Miami Intl., returning Tue, Nov 4, priced at $117 found 23 hours ago
United
Sat, Aug 30 - Wed, Sep 3
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select United flight, departing Sat, Aug 30 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Sep 3, priced at $127 found 2 days ago
JetBlue Airways
Sun, Nov 30 - Thu, Dec 4
BOS
Logan Intl.
EYW
Key West Intl.
$312 Roundtrip, found 5 days ago
$312
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Nov 30 from Logan Intl. to Key West Intl., returning Thu, Dec 4, priced at $312 found 5 days ago