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Key West Vacation Packages

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A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Key West
Florida
United States of America
North America
Hotwire.com

Key West Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Ibis Bay Beach Resort

2.5 out of 5

Price was $993, price is now $736 per person

$736

per person

Sep 28 - Oct 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

Book a stay at this beach hotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

The Key West Hotel

3 out of 5

Save 100% on your flight

Price was $1,770, price is now $1,190 per person

$1,190

per person

Sep 28 - Oct 2

found 1 day 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.

This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Pier House Resort & Spa

4 out of 5

Price was $1,093, price is now $826 per person

$826

per person

Sep 28 - Oct 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Key West (EYW)

Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.

The Gardens Hotel

4 out of 5

Price was $1,182, price is now $896 per person

$896

per person

Sep 20 - Sep 25

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Wonderfully romantic place to celebrate an anniversary. So many special touches.

Reviewed on Aug 9, 2026

Amelia Home by Avantstay In Historic Old Town w/ Pool

3 out of 5

Save 100% on your flight

Price was $3,027, price is now $2,309 per person

$2,309

per person

Sep 19 - Sep 25

found 1 day ago

Roundtrip non-stop flight included

New York (LGA) 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 it

Reviewed on Mar 20, 2026

Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front

3 out of 5

Save 100% on your flight

Price was $2,042, price is now $1,564 per person

$1,564

per person

Sep 20 - Sep 25

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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

Almond Tree Inn Hotel - Adults Only

3.5 out of 5

Price was $1,494, price is now $1,146 per person

$1,146

per person

Sep 20 - Sep 25

found 1 day 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 pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5

Price was $5,393, price is now $4,149 per person

$4,149

per person

Oct 26 - Nov 2

found 11 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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