
Lower Florida Keys Vacation Packages
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Price found within the past 48 hours. Click for updated prices.

3.5-star property
Hyatt Vacation Club at Windward Pointe, Key West
9.6/10 Exceptional! (1,002 reviews)
Mar 13 - Mar 16
3 night stay
Boston (BOS) to Key West (EYW)
JetBlue Airways • Coach
Key West (EYW) to Boston (BOS)
Spirit Airlines • Coach
Price was $1,447, price is now $998 per person
$998
per person
found 1 day ago
Pool and service was great!!! Staff always pleasant and helpful!
Reviewed on Dec 6, 2025

2.5-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (505 reviews)
Mar 21 - Mar 28
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,929, price is now $2,304 per person
$2,304
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025

4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,736 reviews)
Mar 21 - Mar 28
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,001, price is now $1,845 per person
$1,845
per person
found 1 day ago
We LOVED the setting and the surrounding area! Absolutely beautiful!
Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy.
Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you.
The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was.
Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor!
Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am.
Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side.
Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.
Reviewed on Dec 28, 2025

4.0-star property
Southernmost Beach Resort and Guesthouses
Old Town Key West
8.6/10 Excellent! (2,844 reviews)
Mar 21 - Mar 28
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,014, price is now $1,982 per person
$1,982
per person
found 1 day ago
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.
Reviewed on Nov 1, 2025

4.0-star property
The Perry Hotel & Marina Key West
9.4/10 Exceptional! (1,151 reviews)
Mar 21 - Mar 28
7 night stay
Boston (BOS) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,791, price is now $1,882 per person
$1,882
per person
found 1 day ago
Check-in was as smooth as could be. Reps made sure we had access to a luggage cart right away. Property very clean. Room staff could not have been nicer. Would certainly book again
Reviewed on Aug 12, 2025
Top rated hotels for your Lower Florida Keys vacation package

Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
14.08 mi from city center
$140 nightly
The price is $158 total per night
$158 total
Jan 19 - Jan 20
Total with taxes and fees
Guests staying at Looe Key Reef Resort enjoy karaoke, an outdoor pool, and free WiFi in public areas. If you drive, put free parking to good use. Front-desk staff can assist with tours/tickets and luggage storage. Additional amenities include express check-in, a picnic area, and a vending machine.
Pool
Pet friendly

Parmer's Resort
565 Barry Avenue Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
15.31 mi from city center
$258 nightly
The price is $290 total per night
$290 total
Jan 12 - Jan 13
Total with taxes and fees
Guests of Parmer's Resort have access to a private beach, a marina, and an outdoor pool. A stay here includes free parking. The front desk has multilingual staff that can help with luggage storage and concierge services. Other amenities at this beach motel include free WiFi in public areas, coffee/tea in a common area, and a microwave in a common area.
On private beach
Pool

Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
4.06 mi from city center
$169 nightly
The price is $190 total per night
$190 total
Jan 12 - Jan 13
Total with taxes and fees
Guests staying at Sugar Loaf Lodge enjoy access to a marina, an outdoor pool, and outdoor tennis courts. If you drive, take advantage of free parking. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include free WiFi in public areas, a garden, and a vending machine.
Pool
Parking included
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