Search Deals onRobbie's Vacation Packages
Robbie's Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Ibis Bay Beach Resort
Save 100% on your flight
Price was $1,406, price is now $863 per person
$863
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
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. Popular attractions Duval Street and Smathers Beach are located nearby.

The Key West Hotel
Save 100% on your flight
Price was $4,842, price is now $2,848 per person
$2,848
per person
Oct 30 - Nov 6
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Stay at this guesthouse in Key West. Enjoy free WiFi, room service, and daily housekeeping. Popular attractions Duval Street and Mallory Square are located nearby.

Southernmost House - Adult Exclusive
Save 100% on your flight
Price was $2,701, price is now $1,907 per person
$1,907
per person
Oct 30 - Nov 6
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this beach hotel in Key West. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Duval Street and South Beach are located nearby.

The Southernmost Inn - Adults Only
Save 100% on your flight
Price was $2,078, price is now $1,477 per person
$1,477
per person
Oct 31 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Duval Street and South Beach are located nearby.

Blue Flamingo Resort Key West
Save 100% on your flight
Price was $1,371, price is now $990 per person
$990
per person
Oct 30 - Nov 6
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this family-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.

Winslow's Bungalows - Key West Historic Inns
Save 100% on your flight
Price was $1,704, price is now $1,233 per person
$1,233
per person
Oct 30 - Nov 6
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (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.

The Marker Key West Harbor Resort
Save 100% on your flight
Price was $2,893, price is now $2,092 per person
$2,092
per person
Oct 30 - Nov 6
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Mallory Square are located nearby.

Southernmost Beach Resort and Guesthouses
Save 100% on your flight
Price was $2,402, price is now $1,741 per person
$1,741
per person
Oct 30 - Nov 6
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and South Beach are located nearby.

Ella's Cottages - Key West Historic Inns
Save 100% on your flight
Price was $1,926, price is now $1,407 per person
$1,407
per person
Oct 30 - Nov 6
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this 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 Fairhaven House at Solaire Lunara Bay
Save 100% on your flight
Price was $21,130, price is now $15,441 per person
$15,441
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free breakfast, free parking, and a fitness center. Popular attractions Duval Street and Smathers Beach are located nearby.

Springtide House by Brightwild Waterfront Pool
Save 100% on your flight
Price was $11,572, price is now $8,538 per person
$8,538
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Key West (EYW)
Stay at this vacation home in Key West. Enjoy free parking and a garden. Popular attractions Duval Street and Smathers Beach are located nearby.

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $2,066, price is now $1,537 per person
$1,537
per person
Oct 30 - Nov 6
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Key West (EYW)
Book a stay at this 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.
3-4 Night Vacations in Robbie's
Price found within the past 48 hours. Click for updated prices.



5-7 Night Vacations in Robbie's
Price found within the past 48 hours. Click for updated prices.



Robbie's Last Minute Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Book a stay at this 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. ...

The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
Book a stay at this business-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...

DoubleTree Resort by Hilton Grand Key - Key West
3990 S Roosevelt Blvd Key West FL
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...

Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...

Hilton Key West Resort & Marina
5950 Peninsular Avenue Key West FL
Book a stay at this 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 ...

Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
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 ...

Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
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 ...
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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