
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.

The Landon Bay Harbor - Miami Beach
$756
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Book a stay at this business-friendly hotel in Bay Harbor Islands. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Miami Beach Boardwalk and Aventura Mall are located nearby.
I booked by mistake but glad I did. The staff is very nice. The receptionist greeted my beautifully . I asked if my room had a safe because I am a federal employee and need to secure federal equipments. He wasn’t to sure and checked on it when I went to retrieve my luggage, thankfully there was one. On my departure the same receptionist checked me out asked how was my stay. I told him it was my birthday weekend getaway and I had a great time. He shared with me that he also celebrated his birthday a few days ago. So we was both excited being the same sign. He then offered me a bottle of wine complementary on behalf of the hotel on my birthday. I give this hotel a ⭐️⭐️⭐️⭐️⭐️ and will differently booked again.
Reviewed on Aug 19, 2026

The Key West Hotel
Key West Historic District
$6,210
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026

Southernmost House - Adult Exclusive
Old Town Key West
$2,916
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
We had a great time at the Southernmost House. The staff was extremely kind, helpful, and friendly. The food at the bar that we had for breakfast and lunch was fantastic. The house was charming, and while it needs some updating, the staff is actively working to improve the property. We always had a place to park our golf cart and any issue we had was solved quickly. The location was great and we would definitely stay there again.
Reviewed on Aug 20, 2026

Riviere South Beach Hotel
South Beach
$807
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Book a stay at this beach hotel in Miami Beach. Enjoy free WiFi, daily housekeeping, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Lincoln Road Mall are located nearby.
Great place and great location. Very close to the beach and restaurants also stores and shopping. You won't miss out on anything. Staff are very friendly and helpful. It is a decent place to stay clean and all the basics that you need
Reviewed on Aug 21, 2026

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
$2,455
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy a beach locale, balconies, and in-room washers/dryers. Popular attractions Duval Street and Smathers Beach are located nearby.
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .
Reviewed on Mar 26, 2026

Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
Beachside
$2,495
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Key West (EYW)
Book a stay at this beach cottage in Key West. Enjoy free parking, a beach locale, and balconies. Popular attractions Duval Street and Smathers Beach are located nearby.
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 ...

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. ...

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 ...
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, Sep 12 - Thu, Oct 1
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$90
Roundtrip
found 22 hours ago

Mon, Nov 2 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$159
Roundtrip
found 1 day ago

Sat, Jan 30 - Wed, Feb 17
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$159
Roundtrip
found 1 day ago

Tue, Sep 15 - Wed, Sep 16
ORD
O'Hare Intl.
MIA
Miami Intl.
$171
Roundtrip
found 1 hour ago

Tue, Dec 1 - Thu, Dec 3
JFK
John F. Kennedy Intl.
EYW
Key West Intl.
$295
Roundtrip
found 4 days ago
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All accommodation types in Grassy Key
More Types of Hotels
- Hotels with a Pool in Grassy Key
- Oceanfront Hotels in Grassy Key
- Beach Hotels in Grassy Key
- Hotels with WiFi in Grassy Key
- Hotel with wifi in Grassy Key
- Hotels with Air Conditioning in Grassy Key
- Hotels with Bars in Grassy Key
- Family Hotels in Grassy Key
- Hotels with Balconies in Grassy Key
- Smoke Free Hotels in Grassy Key
- Hotels on the River in Grassy Key
- Cheap Hotels in Grassy Key
- Hotel with a Concierge in Grassy Key
- Hotels with Hot Tubs in Grassy Key
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- Luxury Hotels in Grassy Key