Package deals near Southernmost Point

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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! (1,016 reviews)

Jan 11 - Jan 14

3 night stay

Boston (BOS) to Key West (EYW)

JetBlue Airways • Coach

Key West (EYW) to Boston (BOS)

United • Coach
Save 100% on your flight
Price was $1,053, price is now $637 per person
$637
per person
found 1 day ago
Such a nice property

Reviewed on Jun 3, 2025

Winslow's Bungalows - Key West Historic Inns
4.0-star property

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
9.2/10 Wonderful! (1,021 reviews)

Jan 8 - Jan 11

3 night stay

Boston (BOS) to Key West (EYW)

Delta • Non-stop • Coach

Key West (EYW) to Boston (BOS)

Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,236, price is now $696 per person
$696
per person
found 1 day ago
Professional staff, lovely rooms

Reviewed on Oct 21, 2025

Ella's Cottages - Key West Historic Inns
3.5-star property

Ella's Cottages - Key West Historic Inns

Old Town Key West
9.4/10 Exceptional! (378 reviews)

Dec 10 - Dec 17

7 night stay

Boston (BOS) to Key West (EYW)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,099, price is now $1,191 per person
$1,191
per person
found 1 day ago
We chose this historic inn based on central location to everything we wanted in less than 15 min. Front desk staff (Dwight and others) are fantastic and always willing to listen and provide assistance. Fort Zachary Taylor Beach Park is walkable - 25 min (beach water shoes recommended due to rocks). We didn't need to rent any transportation as it was easier for us to walk it out, so I can't comment on parking since I didn't use it (it is limited at most places). We felt very safe walking around, even at night. We used a taxi to and from Key West airport (both drivers familiar with this inn). Room is clean. Both night stands have power and USB charging outlets. Excellent daily room service and Sunshine Breakfast basket hand delivered to your room. Duval Loop bus stop 14 (free) in front of inn (bus route loop is an hour long and two buses running to ensure next bus in 30 min), so this is another convenient option if walking isn't your thing.

Reviewed on Dec 17, 2024

The Key West Hotel
2.5-star property

The Key West Hotel

Key West Historic District
9.2/10 Wonderful! (498 reviews)

Jan 7 - Jan 10

3 night stay

Boston (BOS) to Key West (EYW)

JetBlue Airways • Coach

Key West (EYW) to Boston (BOS)

American Airlines • Coach
Save 100% on your flight
Price was $1,888, price is now $1,076 per person
$1,076
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

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

Oceans Edge Key West Resort, Hotel & Marina

8.8/10 Excellent! (1,732 reviews)

Dec 10 - Dec 17

7 night stay

Boston (BOS) to Key West (EYW)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,511, price is now $886 per person
$886
per person
found 1 day ago
great property, transportation to key west great, missing an additional dining option. Everything else was fantastic

Reviewed on Sep 21, 2025

Hyatt Vacation Club at Beach House, Key West
3.5-star property

Hyatt Vacation Club at Beach House, Key West

9.4/10 Exceptional! (1,010 reviews)

Jan 8 - Jan 11

3 night stay

Boston (BOS) to Key West (EYW)

Delta • Non-stop • Coach

Key West (EYW) to Boston (BOS)

Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,112, price is now $671 per person
$671
per person
found 1 day ago
The property was truly amazing. We.rented a 2 bedroom villa and it was comfortable and very well decorated and equipped. The only complaint would be the " complimentary breakfast" needs to be better. It was only a selection of cruisants with water and orange juice. For the price spent, please add eggs, meat and coffee at least. Other than that, it was very nice

Reviewed on Sep 7, 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
$242 nightly
The price is $272 total per night
$272 total
Nov 30 - Dec 1
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, luggage storage, and tours or tickets. Other amenities at this beach hotel include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street, Key West, FL
Free Cancellation
Reserve now, pay when you stay
0.46 mi from Southernmost Point
$307 nightly
The price is $346 total per night
$346 total
Dec 1 - Dec 2
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton features a private beach, a full-service spa, and 2 outdoor pools. Valet parking is offered for USD 50 per day. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, luggage storage, and dry cleaning/laundry. Other amenities at this beach resort include a gym, free WiFi in public areas, and conference space.
On private beach
Pool
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
$290 nightly
The price is $327 total per night
$327 total
Nov 20 - Nov 21
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 concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this beach resort include a gym, WiFi in public areas, and meeting rooms.
On private beach
Pool
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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.