Search Deals onKey West Vacation Packages
Key West Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Lighthouse Hotel - Key West Historic Inns
Price was $1,163, price is now $787 per person
$787
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
We flew down to Key West for a much needed relaxing getaway. The location of the Lighthouse is perfect - centrally located and easy to navigate all the island has to offer, yet tucked just off Duval St so you feel like you’re in a quiet area at night. The pool is refreshing and the rooms are small but clean and the entire place has a very island feel. We enjoyed each day and can’t wait to return.
Reviewed on Aug 25, 2026
The Key West Hotel
Save 100% on your flight
Price was $3,321, price is now $2,034 per person
$2,034
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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
Parrot Key Hotel & Villas
Price was $1,522, price is now $1,068 per person
$1,068
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 4 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.
Kona Kai Oasis
Save 100% on your flight
Price was $1,588, price is now $1,122 per person
$1,122
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Duval Street and Southernmost Point are located nearby.
La propiedad está bien ubicada… no hay personal físico para la atención … pero todo se puede realizar vía telefónica, inmediatamente responden y dan solución a tus inquietudes… todo muy bien…
Reviewed on Aug 22, 2026
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
Save 100% on your flight
Price was $3,656, price is now $2,611 per person
$2,611
per person
Nov 8 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Save 100% on your flight
Price was $3,384, price is now $2,496 per person
$2,496
per person
Nov 16 - Nov 21
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Stay at this cottage in Key West. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Loved the closeness to Duval st and the privacy
Reviewed on Oct 17, 2025
The Gardens Hotel
Price was $1,756, price is now $1,310 per person
$1,310
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Key West (EYW)
Book a stay at this business-friendly B&B in Key West. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
We had an amazing three night stay. It was a quiet place and the rooms were amazing!
We highly recommend this place. Location is good.
Reviewed on Aug 25, 2026
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Save 100% on your flight
Price was $3,169, price is now $2,372 per person
$2,372
per person
Nov 12 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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
Key West Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Key West Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Sep 14 - Thu, Sep 17
PIE
St. Petersburg-Clearwater Intl.
EYW
Key West Intl.
$86 Roundtrip, found 12 hours ago
$86
Roundtrip
found 12 hours ago
Mon, Sep 14 - Thu, Sep 17
TPA
Tampa Intl.
EYW
Key West Intl.
$98 Roundtrip, found 12 hours ago
$98
Roundtrip
found 12 hours ago
Tue, Nov 10 - Thu, Nov 26
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$299 Roundtrip, found 6 days ago
$299
Roundtrip
found 6 days ago
Wed, Oct 7 - Wed, Oct 14
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$328 Roundtrip, just found
$328
Roundtrip
just found
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