Grassy Key Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Grassy Key Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Creekside Inn
Price was $1,255, price is now $524 per person
$524
per person
Apr 19 - Apr 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this motel in Tavernier. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Florida Keys Dive Center and Mangrove Marina are located nearby.
President Hotel
South Beach
Save 100% on your flight
Price was $1,275, price is now $738 per person
$738
per person
Apr 22 - Apr 26
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Stay at this hotel in Miami Beach. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
The Penguin Hotel
South Beach
Save 100% on your flight
Price was $1,176, price is now $688 per person
$688
per person
Apr 22 - Apr 26
found 20 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $3,199, price is now $1,914 per person
$1,914
per person
May 2 - May 7
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $943, price is now $585 per person
$585
per person
May 28 - Jun 1
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, a beach locale, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.
Lux Retreat By Renzzi
Little Havana
Save 100% on your flight
Price was $1,536, price is now $955 per person
$955
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this apartment in Miami. Enjoy free WiFi, daily housekeeping, and rainfall showerheads. Popular attractions Brickell City Centre and Kaseya Center are located nearby.
Top Hotel Deals
Rainbow Bend Resort
57784 Overseas Hwy Marathon FL
0.97 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
58182 Overseas Hwy Marathon FL
0.37 km from city center
Stay at this hotel in Marathon. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition in our reviews. ...
Gulf View Waterfront Resort
58743 OVERSEAS HWY Marathon FL
0.54 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. ...
Isla Bella Beach Resort & Spa
1 Knights Key Boulevard Marathon FL
17.99 km from city center
Book a stay at this 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 ...
Hawks Cay Resort
61 Hawks Cay Blvd Marathon FL
4.54 km from city center
Book a stay at this 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 ...
Lime Tree Bay Resort
68500 Overseas Hwy Long Key FL
15.5 km from city center
Book a stay at this 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. ...
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
2146 Overseas Hwy Marathon FL
16.31 km from city center
Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 2 outdoor pools, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. ...
Kingsail Resort
7050 Overseas Highway Marathon FL
12.22 km from city center
Stay at this motel in Marathon. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Fairfield Inn & Suites by Marriott Marathon Florida Keys
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 ...
Coconut Cay Resort & Marina
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 ...
Floating Sea Cove Resort & Marina
12685 Overseas Highway Marathon FL
7.02 km from city center
Stay at this hotel in Marathon. Enjoy free parking and air conditioning. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions ...
Tranquility Bay Beachfront Hotel and Resort
2600 Overseas Hwy Marathon FL
15.94 km from city center
Book a stay at this 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. ...
Banana Bay Resort & Marina
4590 Overseas Highway Marathon FL
14.31 km from city center
Book a stay at this golf hotel in Marathon. Enjoy free breakfast, a marina, and free bicycles on site. Our guests praise the pool and the helpful staff in our ...
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.
Tue, May 19 - Wed, May 20
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$67 Roundtrip, found 7 hours ago
$67
Roundtrip
found 7 hours ago
Fri, Apr 17 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$70 Roundtrip, found 14 hours ago
$70
Roundtrip
found 14 hours ago
Wed, Jun 3 - Wed, Jun 10
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Fri, Apr 17 - Mon, Apr 20
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Sat, Apr 11 - Fri, Apr 17
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days ago