Name: Beachside Resort & Residences
Price range: $217 total
Rating: 8.6

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The Latest Raccoon Key vacation packages

Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$548

per person

Jan 20 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.8/10 Excellent! (1,732 reviews)

Overall the stay was nice. The “poolside bar” that really didn’t exist was one of the top reasons I booked this place. They did have a server they came out, every once in awhile, even that ended early, at 4. Once the sun set the life of the hotel went with it. Restaurant staff weren’t the friendliest, but if you have the privilege of meeting Jeffrey on the shuttle you hit the lotto. You get your own key west tour guide. He was a delight. The girls out at the Tiki Hut, Alena and Liz were very welcoming and helpful as well.

Reviewed on Nov 7, 2025

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$1,462

per person

Dec 21 - Dec 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,021 reviews)

Good breakfast. Nice pools.

Reviewed on Nov 6, 2025

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,148

per person

Jan 20 - Jan 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (498 reviews)

location was great nice bar party vibe

Reviewed on Nov 8, 2025

Hyatt Vacation Club at Beach House, Key West

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$1,198

per person

Jan 10 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,010 reviews)

The room was spotless and staff incredibly helpful. We enjoyed the pool the most and it was convenient to be a 10 minute drive away from Duval Street.

Reviewed on Nov 7, 2025

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

$647

per person

Jan 10 - Jan 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.6/10 Exceptional! (1,016 reviews)

Very friendly and helpful staff.

Reviewed on Nov 7, 2025

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Raccoon Key Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Fully refundableReserve now, pay when you stay

$208 nightly

$234 total

Nov 30 - Dec 1

Total with taxes and fees

8.8/10 Excellent! (1,733 reviews)

We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate.

Reviewed on Nov 2, 2025

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard, Key West, FL

Fully refundableReserve now, pay when you stay

$157 nightly

$177 total

Nov 17 - Nov 18

Total with taxes and fees

7.8/10 Good! (1,663 reviews)

Great staff!

Reviewed on Nov 6, 2025

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

Fully refundableReserve now, pay when you stay

$193 nightly

$217 total

Nov 17 - Nov 18

Total with taxes and fees

8.6/10 Excellent! (1,655 reviews)

Staff good but never clean our room

Reviewed on Nov 3, 2025

See all 3,220 properties in Raccoon Key

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.