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.
Ella's Cottages - Key West Historic Inns
Old Town Key West
$992
per person
Oct 29 - Nov 3
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
We had a wonderful stay at Ella’s cottages. The staff were so wonderful. Happy hour at the pool was really fun. The only complaint I have is there was construction right behind our room, but that’s not the hotels fault.
Reviewed on Aug 11, 2026
iCoconutGrove Vacation Rentals
Coconut Grove
$1,645
per person
Nov 6 - Nov 14
found 2 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Book a stay at this golf hotel in Miami. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions LoanDepot Park and Brickell City Centre are located nearby.
location is perfect, close to restaurant and shop ,clean quiet and have everything we need.
Reviewed on Aug 14, 2026
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
$1,016
per person
Oct 29 - Nov 3
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (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.
Very private and personal. Breakfast and Bar was very nice and relaxing.
Reviewed on Aug 16, 2026
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
$1,025
per person
Oct 29 - Nov 3
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Nice property! We will be back. Super friendly staff.
Reviewed on Aug 16, 2026
Ridley House - Key West Historic Inns
Key West Historic District
$1,083
per person
Oct 29 - Nov 3
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
This is a must stay property! It is walking distance to everything. Your very cold room with the softest mattress ever is always 7 minutes away or less.
Reviewed on Aug 13, 2026
The Marker Key West Harbor Resort
Key West Historic District
$1,526
per person
Oct 29 - Nov 3
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.
Disappointed in room, we've stayed here many, many times and this was disappointing. Also, the amount of people that use the amenities that are not staying at resort OR paying resort fees.
Reviewed on Aug 14, 2026
Top Hotel Deals
Rainbow Bend Resort
57784 Overseas Hwy Marathon FL
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
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
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
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
Book a stay at this luxury hotel in Marathon. Enjoy free WiFi, 3 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
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. ...
Tranquility Bay Beachfront Hotel and Resort
2600 Overseas Hwy Marathon FL
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. ...
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton
1996 Overseas Highway Marathon FL
Book a stay at this spa resort in Marathon. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. ...
Fairfield Inn & Suites by Marriott Marathon Florida Keys
13201 Overseas Hwy Marathon FL
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 ...
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
2146 Overseas Hwy Marathon FL
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. ...
Banana Bay Resort & Marina
4590 Overseas Highway Marathon FL
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 ...
Kingsail Resort
7050 Overseas Highway Marathon FL
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 ...
Coconut Cay Resort & Marina
7196 Overseas Highway Marathon FL
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 ...
Hampton Inn Marathon - Florida Keys
13351 Overseas Highway Marathon FL
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 ...
Captain Pips Marina & Hideaway
1480 Overseas Hwy Marathon FL
Stay at this 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. ...
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.
Sat, Nov 7 - Wed, Nov 18
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$90
Roundtrip
found 1 day ago
Mon, Oct 5 - Sat, Oct 17
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$153
Roundtrip
found 2 days ago
Tue, Oct 20 - Tue, Oct 27
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$159
Roundtrip
found 10 hours ago
Tue, Sep 15 - Tue, Sep 29
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$189
Roundtrip
found 3 hours ago
Tue, Oct 6 - Sat, Oct 17
BOS
Logan Intl.
MIA
Miami Intl.
$238
Roundtrip
found 2 days ago
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