Cutthroat Harbor Estates Travel Guide
Summerland Key
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Top hotels in Cutthroat Harbor Estates
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
The price is 3.471.466 ₫ per night from 16 Jul to 17 Jul
3.471.466 ₫
6.419.924 ₫ total
16 Jul - 17 Jul
includes taxes & fees
Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 2 restaurants and a private beach. Our guests praise the pool and the helpful staff in their reviews. ...
8.6/10 Excellent! (2,333 reviews)
"Our stay was truly memorable and I would recommend to everyone!!!"
Reviewed on 8 Jul 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
The price is 3.289.379 ₫ per night from 13 Jul to 14 Jul
3.289.379 ₫
5.179.590 ₫ total
13 Jul - 14 Jul
includes taxes & fees
Stay at this family-friendly hotel in Key West. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
8.4/10 Very good! (2,510 reviews)
"My favorite place I’ve stayed ever. My wife and I spent the first 3 nights of our honeymoon at the Blue Flamingo Resort. We spent most of one our days at the resort. Honestly, we could have stayed there the whole time but we booked a lot. We had the Oceanview King room. We loved the pool. We enjoyed ..."
Reviewed on 8 Jul 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
The price is 3.711.013 ₫ per night from 4 Aug to 5 Aug
3.711.013 ₫
4.914.568 ₫ total
4 Aug - 5 Aug
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge) and a free local area shuttle. Our guests praise the pool and the ...
8/10 Very good! (1,272 reviews)
"Staff super friendly, and overall it’s a nice hotel. The traffic was loud if you stayed in the front building. It was also difficult to make a left turn out of the parking lot onto Rosevelt Dr."
Reviewed on 8 Jul 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
The price is 3.407.702 ₫ per night from 28 Jul to 29 Jul
3.407.702 ₫
5.499.127 ₫ total
28 Jul - 29 Jul
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,825 reviews)
"What an amazing experience. Can't wait to visit again soon."
Reviewed on 9 Jul 2026
Hyatt Vacation Club at Windward Pointe, Key West
3675 South Roosevelt Boulevard Key West FL
The price is 8.323.787 ₫ per night from 8 Aug to 9 Aug
8.323.787 ₫
10.547.490 ₫ total
8 Aug - 9 Aug
includes taxes & fees
Stay at this hotel in Key West. Enjoy free Wi-Fi, free parking and a snack bar/deli. Our guests praise the pool and the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (1,181 reviews)
"I highly recommend this property! The place was beautiful and the pool and grounds really lovely. Can't wait to go back."
Reviewed on 8 Jul 2026
The Perry Hotel & Marina Key West
7001 Shrimp Road Key West FL
Fully refundable
The price is 4.029.030 ₫ per night from 26 Jul to 27 Jul
4.029.030 ₫
6.116.084 ₫ total
26 Jul - 27 Jul
includes taxes & fees
Stay at this business-friendly hotel in Key West. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their ...
9.4/10 Exceptional! (1,292 reviews)
"This hotel is amazing! The view, the location, the cleanliness, the staff, everything was perfect! We enjoyed a week long stay for my 40th birthday and didn’t want to leave! The shower was HUGE in the king bed room we stayed in. The bed itself was comfortable and had a pull out sofa bed for the kids. ..."
Reviewed on 8 Jul 2026
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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Where to stay in Cutthroat Harbor Estates
Find the best Cutthroat Harbor Estates areas for the activities you enjoy most.
Sugarloaf Shores
Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.
Bay Point
While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.
Cudjoe Gardens
While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Florida Keys Beaches.
Breezeswept Beach Estates
While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Cook Island and Big Pine Key Flea Market.
