Truman Annex Vacation Packages for 2025

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Truman Annex Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this 3.5-star hotel in Key West. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this 4-star hotel in Key West. Enjoy free breakfast, free WiFi, and 3 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this 3.5-star 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.

Ella's Cottages - Key West Historic Inns

Ella's Cottages - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this 3.5-star business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
per person
Jul 11 - Jul 15
found 1 day ago
Roundtrip flight included
Washington (DCA) to Key West (EYW)
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Smathers Beach are located nearby.

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Top Hotel Deals

Weatherstation Inn

Weatherstation Inn

2.5 out of 5
57 Front St, Key West, FL
0.14 km from Truman Annex
Book a stay at this boutique B&B in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 out of 5
200 Sunset Lane, Key West, FL
0.3 km from Truman Annex
Stay at this 3.5-star apartment in Key West. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Duval Street and Mallory Square ...
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
5.82 km from Truman Annex
Stay at this 3.5-star beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
1.32 km from Truman Annex
Stay at this 4-star beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the bar in our reviews. ...
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
8.03 km from Truman Annex
Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
3.56 km from Truman Annex
Stay at this 4-star beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd, Key West, FL
4.16 km from Truman Annex
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. ...
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road, Key West, FL
6.99 km from Truman Annex
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
5.76 km from Truman Annex
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

3 out of 5
2400 N Roosevelt Blvd, Key West, FL
3.26 km from Truman Annex
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
4.97 km from Truman Annex
Stay at this 4-star business-friendly hotel in Key West. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in ...
Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
1 Duval St, Key West, FL
0.72 km from Truman Annex
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and 2 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
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
1.52 km from Truman Annex
Stay at this 4-star beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

4 out of 5
601 Front St, Key West, FL
0.86 km from Truman Annex
Book a stay at this beach resort in Key West. Enjoy free WiFi, a full-service spa, and a marina. Our guests praise the pool and the bar in our reviews. Popular ...
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

4 out of 5
430 Duval St, Key West, FL
0.47 km from Truman Annex
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Jun 24 - Wed, Jul 2
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$249 Roundtrip, found 2 days ago
$249
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jun 24 from Newark Liberty Intl. Airport to Key West Intl., returning Wed, Jul 2, priced at $249 found 2 days ago
Delta
Thu, Sep 11 - Mon, Sep 15
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$259 Roundtrip, found 4 days ago
$259
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 11 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Mon, Sep 15, priced at $259 found 4 days ago
JetBlue Airways
Mon, Aug 18 - Tue, Aug 19
LGA
LaGuardia
EYW
Key West Intl.
$262 Roundtrip, found 4 days ago
$262
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Aug 18 from LaGuardia to Key West Intl., returning Tue, Aug 19, priced at $262 found 4 days ago
JetBlue Airways
Fri, Jun 20 - Tue, Jun 24
JFK
John F. Kennedy Intl.
EYW
Key West Intl.
$312 Roundtrip, found 4 days ago
$312
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Jun 20 from John F. Kennedy Intl. to Key West Intl., returning Tue, Jun 24, priced at $312 found 4 days ago