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
Aug 2 - Aug 6
found 1 day ago
Roundtrip flight included
New York (JFK) 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.

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Miami (MIA)
Stay at this 4.5-star luxury hotel in Miami Beach. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Key West (EYW)
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

Trump International Beach Resort

Trump International Beach Resort

4.5 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Miami (MIA)
Stay at this 4.5-star luxury hotel in Sunny Isles Beach. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Aventura Mall and Hollywood Beach are located nearby.

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Sep 4 - Sep 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Key West (EYW)
Stay at this 3.5-star 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.

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 4 - Sep 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 ...
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. ...
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 ...
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. ...
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. ...
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. ...
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 ...
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. ...
Banana Bay Resort & Marina

Banana Bay Resort & Marina

3 out of 5
4590 Overseas Highway, Marathon, FL
14.31 km from city center
Stay at this 3-star golf hotel in Marathon. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the bar in our reviews. Popular ...
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. ...
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 ...
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 ...
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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.

Delta
Tue, Nov 11 - Tue, Nov 18
BOS
Logan Intl.
MIA
Miami Intl.
$97 Roundtrip, found 6 days ago
$97
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Nov 11 from Logan Intl. to Miami Intl., returning Tue, Nov 18, priced at $97 found 6 days ago
American Airlines
Sat, Sep 13 - Sun, Sep 21
PHL
Philadelphia Intl.
MIA
Miami Intl.
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 13 from Philadelphia Intl. to Miami Intl., returning Sun, Sep 21, priced at $108 found 2 days ago
Frontier Airlines
Wed, Aug 20 - Wed, Aug 27
LGA
LaGuardia
MIA
Miami Intl.
$111 Roundtrip, found 19 hours ago
$111
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Wed, Aug 20 from LaGuardia to Miami Intl., returning Wed, Aug 27, priced at $111 found 19 hours ago
Spirit Airlines
Thu, Jul 24 - Thu, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Thu, Jul 31, priced at $118 found 3 days ago