Package deals near Southernmost Point

Save more on your trip when booking your flight + hotel together

Top Southernmost Point vacation deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West
3.5-star property

Hyatt Vacation Club at Windward Pointe, Key West

9.6/10 Exceptional! (1,002 reviews)

Feb 27 - Mar 2

3 night stay

Boston (BOS) to Key West (EYW)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,174, price is now $729 per person
$729
per person
found 1 day ago
Pool and service was great!!! Staff always pleasant and helpful!

Reviewed on Dec 6, 2025

Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

9/10 Wonderful! (1,736 reviews)

Feb 12 - Feb 19

7 night stay

Boston (BOS) to Key West (EYW)

Spirit Airlines • Non-stop • Coach

Key West (EYW) to Boston (BOS)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $4,282, price is now $2,514 per person
$2,514
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

The Key West Hotel
2.5-star property

The Key West Hotel

Key West Historic District
9.2/10 Wonderful! (505 reviews)

Mar 12 - Mar 16

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,900, price is now $1,768 per person
$1,768
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

Southernmost Beach Resort and Guesthouses
4.0-star property

Southernmost Beach Resort and Guesthouses

Old Town Key West
8.6/10 Excellent! (2,844 reviews)

Feb 1 - Feb 7

6 night stay

Boston (BOS) to Key West (EYW)

Spirit Airlines • Non-stop • Coach

Key West (EYW) to Boston (BOS)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,666, price is now $1,693 per person
$1,693
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

The Perry Hotel & Marina Key West
4.0-star property

The Perry Hotel & Marina Key West

9.4/10 Exceptional! (1,151 reviews)

Feb 1 - Feb 7

6 night stay

Boston (BOS) to Key West (EYW)

Spirit Airlines • Non-stop • Coach

Key West (EYW) to Boston (BOS)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,516, price is now $1,620 per person
$1,620
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

Havana Cabana at Key West
4.0-star property

Havana Cabana at Key West

New Town
8.8/10 Excellent! (1,749 reviews)

Mar 20 - Mar 24

4 night stay

Minneapolis (MSP) to Key West (EYW)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,026, price is now $2,092 per person
$2,092
per person
found 1 day ago
The bartenders were wonderful.

Reviewed on Jul 2, 2025

Hotel deals near Southernmost Point

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
0.09 mi from Southernmost Point
$419 nightly
The price is $472 total per night
$472 total
Jan 26 - Jan 27
Total with taxes and fees
Guests of Southernmost Beach Resort and Guesthouses have access to a full-service spa, 3 outdoor pools, and a gym. Self parking is offered for USD 53.75 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this beach hotel include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street Key West FL
Free Cancellation
Reserve now, pay when you stay
0.2 mi from Southernmost Point
$381 nightly
The price is $428 total per night
$428 total
Jan 13 - Jan 14
Total with taxes and fees
Guests of The Reach Key West, Curio Collection by Hilton have access to a private beach, a full-service spa, and an outdoor pool. Valet parking is offered for USD 50 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and tours or tickets. Other amenities at this beach resort include a gym, WiFi in public areas, and meeting rooms.
On private beach
Pool
Southernmost House

Southernmost House

4 out of 5
1400 Duval Street Key West FL
0.07 mi from Southernmost Point
$450 nightly
The price is $506 total per night
$506 total
Jan 15 - Jan 16
Total with taxes and fees
At Southernmost House, guests have access to an outdoor pool, free WiFi in public areas, and coffee in a common area. Self parking is available for USD 25 per night. The front desk has multilingual staff that can help with concierge services, luggage storage, and securing valuables. Other amenities at this adults-only hotel include free newspapers, a terrace, and a TV in a common area.
Pool
Breakfast included
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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.

Book a Southernmost Point vacation package

Stop dreaming and start traveling. If you’ve always wanted to see Southernmost Point, now is the perfect time. Book your getaway to Key West with Orbitz and get ready to tick this attraction off your bucket list. Plus when you lock in your package with us, you’ll have plenty of cash leftover to splash out on other amazing Key West sights. Because travel is all about investing in experiences, not things!

If you’re hoping to stay close to Southernmost Point, we’ve got you covered. Choose from a great range of hotels not far from this attraction. Roll out of bed, slip on your walking shoes and you’ll be there within moments. What could be more convenient than that? You won’t just be close to all the action — you’ll save money on transportation, and a hot shower and cozy bed will be within reach after a big day of exploring. Now that’s what we call a stress- free, full-of-fun getaway.

Orbitz has your ticket to a rewarding Southernmost Point vacation. Book your Key West package with us and you’ll be able to access Orbitz Rewards. Earn Orbucks when you reserve your flights, hotels and activities with Orbitz and redeem them at over 385,000 hotels worldwide. $1 Orbuck = $1 off your next hotel. Join, earn, redeem — just like that! When you join Orbitz Rewards, you’ll also instantly unlock exclusive deals and save on thousands of properties with Insider Pricing.

We believe the best reward that you can give to yourself or others is the gift of travel. So, don’t put off exploring Southernmost Point any longer. Save a bundle and book your Key West escape with Orbitz today.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.