Cutthroat Harbor Estates Vacation Packages for 2025

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Cutthroat Harbor Estates Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Solé Miami, A Noble House Resort

Solé Miami, A Noble House Resort

4 out of 5
Save 100% on your flight
per person
Jun 26 - Jun 30
found 8 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Stay at this 4-star beach hotel in Sunny Isles Beach. Enjoy a beach locale, breakfast (surcharge), and room service. Our guests praise the pool and the restaurant in our reviews. Popular attractions Aventura Mall and Gulfstream Park Racing and Casino are located nearby.

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jun 26 - Jun 30
found 8 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Stay at this 4.5-star luxury hotel in Miami Beach. 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 Collins Avenue Shopping Area and Ocean Drive are located nearby.

B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jun 26 - Jun 30
found 8 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Stay at this 4-star beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Las Olas Beach and Port Everglades are located nearby.

Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jun 26 - Jun 30
found 8 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Book a stay at this luxury resort in Miami Beach. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

Trump International Beach Resort

Trump International Beach Resort

4.5 out of 5
Save 100% on your flight
per person
Jun 26 - Jun 30
found 8 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Stay at this 4.5-star luxury hotel in Sunny Isles Beach. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Aventura Mall and Hollywood Beach are located nearby.

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Jun 26 - Jun 30
found 8 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
Book a stay at this beach hotel in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Little Conch Key and Walkers Island are located nearby.

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Top Hotel Deals

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
27.43 km from Cutthroat Harbor Estates
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 ...
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
29.43 km from Cutthroat Harbor Estates
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. ...
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road, Key West, FL
28.35 km from Cutthroat Harbor Estates
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 ...
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
30.29 km from Cutthroat Harbor Estates
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 ...
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
29.48 km from Cutthroat Harbor Estates
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 ...
The Gates Hotel Key West Newly Renovated

The Gates Hotel Key West Newly Renovated

4 out of 5
3824 N Roosevelt Blvd, Key West, FL
29.54 km from Cutthroat Harbor Estates
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
Fairfield Inn & Suites by Marriott Key West at the Keys Collection

Fairfield Inn & Suites by Marriott Key West at the Keys Collection

3.5 out of 5
3852 North Roosevelt Boulevard, Key West, FL
29.49 km from Cutthroat Harbor Estates
Book a stay at this eco-certified hotel in Key West. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in ...
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd, Key West, FL
29.76 km from Cutthroat Harbor Estates
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard, Key West, FL
29.97 km from Cutthroat Harbor Estates
Stay at this 3.5-star 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. ...
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd, Key West, FL
29.6 km from Cutthroat Harbor Estates
Stay at this 4-star 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

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
29.61 km from Cutthroat Harbor Estates
Stay at this 4-star eco-certified hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
5051 Overseas Highway, Key West, FL
29.21 km from Cutthroat Harbor Estates
Stay at this 3.5-star hotel in Key West. Enjoy free WiFi, free parking, and concierge services. Our guests praise the helpful staff and the clean rooms in our ...
Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

2 out of 5
5130 Overseas Hwy, Key West, FL
28.86 km from Cutthroat Harbor Estates
Stay at this houseboat in Key West. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Duval ...
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
7.2 km from Cutthroat Harbor Estates
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the bar and the helpful staff in our reviews. ...
Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 out of 5
1791 Bogie Drive, Big Pine Key, FL
13.82 km from Cutthroat Harbor Estates
Stay at this cottage in Big Pine Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Blue ...
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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.

Silver Airways
Tue, Oct 7 - Mon, Oct 13
TPA
Tampa Intl.
EYW
Key West Intl.
$77 Roundtrip, found 3 days ago
$77
Roundtrip
found 3 days ago
Select Silver Airways flight, departing Tue, Oct 7 from Tampa Intl. to Key West Intl., returning Mon, Oct 13, priced at $77 found 3 days ago
Delta
Tue, Jun 10 - Mon, Jun 16
BOS
Logan Intl.
EYW
Key West Intl.
$247 Roundtrip, found 5 days ago
$247
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jun 10 from Logan Intl. to Key West Intl., returning Mon, Jun 16, priced at $247 found 5 days ago
Delta
Mon, Aug 25 - Wed, Sep 3
ORD
O'Hare Intl.
EYW
Key West Intl.
$269 Roundtrip, just found
$269
Roundtrip
just found
Select Delta flight, departing Mon, Aug 25 from O'Hare Intl. to Key West Intl., returning Wed, Sep 3, priced at $269 just found
JetBlue Airways
Wed, Nov 12 - Mon, Nov 17
PHL
Philadelphia Intl.
EYW
Key West Intl.
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Nov 12 from Philadelphia Intl. to Key West Intl., returning Mon, Nov 17, priced at $326 found 1 day ago