Exclusive Southernmost Point Vacation Deals

Southernmost Point vacation package deals

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

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
Price was $1,774, price is now $1,286 per person
$1,286
per person
Jan 9 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.
The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was $7,801, price is now $4,969 per person
$4,969
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
Price was $5,121, price is now $3,620 per person
$3,620
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a 24-hour gym.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

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

3 out of 5
Old Town Key West
Price was $4,716, price is now $3,344 per person
$3,344
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.
Grand Maloney Hotel

Grand Maloney Hotel

2 out of 5
Key West Historic District
Price was $1,872, price is now $1,368 per person
$1,368
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and a terrace. Laundry facilities and wedding services are also provided.
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool

3 out of 5
Save 100% on your flight
Price was $3,932, price is now $2,883 per person
$2,883
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
An outdoor pool is featured at this cottage, along with free WiFi in public areas.

Frequently asked questions

How much are vacation packages to Southernmost Point?
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Where can I get the best vacation package deals for Southernmost Point?
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Top Southernmost Point hotel deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$279 nightly
The price is $314 total per night
$314 total
Nov 30 - Dec 1
Total with taxes and fees
A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and laundry service. 2 poolside bars and 2 bars/lounges are featured at this hotel, along with a gym.
Pool
Spa
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

3 out of 5
525 United Street Key West FL
Free Cancellation
Reserve now, pay when you stay
$204 nightly
The price is $229 total per night
$229 total
Nov 18 - Nov 19
Total with taxes and fees
This hotel's 2 outdoor pools and hot tub are among the featured amenities. Enjoy the free continental breakfast each morning. Self parking, a coffee shop, and a terrace are also offered.
Pool
Hot Tub
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
$289 nightly
The price is $325 total per night
$325 total
Dec 14 - Dec 15
Total with taxes and fees
This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. Enjoy the outdoor pool and unwind at the bar/lounge and poolside bar.
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.

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