Fleming Key Vacations from $491

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The Latest Fleming Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Iberostar Waves Miami Beach
Bay Breeze Premium Apartments By Eskape Collection
Iberostar Waves Berkeley Shore
Hawks Cay Resort
Cavalier Hotel South Beach
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Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.

Fleming Key Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $223 total per night from Dec 2 to Dec 3
$223 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (1,720 reviews)
Great room, restaurant, and shuttle!

Reviewed on Nov 26, 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $177 total per night from Dec 2 to Dec 3
$177 total
Dec 2 - Dec 3
Total with taxes and fees
7.8/10 Good! (1,730 reviews)
Everything was beautiful and it was a pleasure to stay there. Will stay again.

Reviewed on Nov 25, 2025

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $228 total per night from Dec 2 to Dec 3
$228 total
Dec 2 - Dec 3
Total with taxes and fees
8.8/10 Excellent! (1,748 reviews)
The property was beautiful. The staff was welcoming and helpful. The room and accommodations were wonderful. Enjoyed the convenience of the concierge services as well as the shuttle. Everyone from the bellmen Sam to the shuttle drivers were friendly and made the time spent on property a joy.

Reviewed on Nov 25, 2025

Oceans Edge Key West Resort, Hotel & Marina
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.

Find the Best Fleming Key Vacation Packages

Fleming Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Miami Intl. Airport (MIA)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.