
Rockland Key Vacations from $729
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Rockland Key vacation packages
Price found within the past 48 hours. Click for updated prices.

Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,174, price is now $729 per person
$729
per person
Feb 27 - Mar 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Room was clean, the grounds are very well kept. Only issue the front desk didn't explain housekeeping needed to be requested 24 hours in advance so we ended up with overflowing trash. Also requesting extra towels was a pain as most of the time we had to call multiple times. Overall we would stay again.
Reviewed on Jan 1, 2026

The Key West Hotel
Key West Historic District
Price was $2,589, price is now $1,419 per person
$1,419
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.
Reviewed on Dec 12, 2025

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,562, price is now $960 per person
$960
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The room was good, the staff was very helpful and very kind
Reviewed on Dec 31, 2025

The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $3,017, price is now $1,875 per person
$1,875
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
We absolutely loved the hotel! The house was classic Key west, so spotless, the staff was fantastic, the tortises and birds were definately entertaining, the pool was heavenly and being greeted with a glass of Proscuitta definately started the vacation off perfectly. We will definately be back!!
Reviewed on Dec 27, 2025

Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,871, price is now $1,204 per person
$1,204
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
Nice clean room, scenic views, accessible area
Reviewed on Dec 30, 2025
Don't see what you're looking for?
See all available trips from Columbus to Rockland Key
View all tripsRockland Key Hotel Deals

Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$309 nightly
The price is $347 total per night from Jan 8 to Jan 9
$347 total
Jan 8 - Jan 9
Total with taxes and fees
8.6/10 Excellent! (1,835 reviews)
Pool and hot tub were very nice,chicken walk was excellent! Great staff!!!!
Reviewed on Dec 26, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$292 nightly
The price is $329 total per night from Jan 4 to Jan 5
$329 total
Jan 4 - Jan 5
Total with taxes and fees
8/10 Very Good! (1,803 reviews)
The room was very clean and comfortable. The $15.00 for parking your car was a little of the top tho! You should really give discounts for Florida Residence too, we drove 350 miles to come see Key West and to have to pay all the fees & parking fee is a bit much!
Reviewed on Dec 26, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$275 nightly
The price is $309 total per night from Jan 6 to Jan 7
$309 total
Jan 6 - Jan 7
Total with taxes and fees
8.8/10 Excellent! (1,763 reviews)
So many activities and amazing staff and service. The shuttle was very convenient. I would stay here again! Perfect for families. I felt safe. Very laid back environment.
Reviewed on Dec 26, 2025
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 Rockland Key Vacation Packages
Rockland Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
More vacations you might like
Explore a world of travel with Expedia
- Key West Hotels
- All-inclusive Resorts in Key West
- Big Coppitt Key Hotels
- RV Parks in Big Coppitt Key
- Hotels near Geiger Key
- Boca Chica Key Hotels
- Beach Hotels in Boca Chica Key
- RV Parks in Boca Chica Key
- Hotels near Boca Chica Nude Beach
- Hotels near Stock Island Yacht Club & Marina
- Key Haven Hotels
- Hotels near Saddlebunch Keys
- Raccoon Key Hotels
- Cottages in Raccoon Key
- 4 Star Hotels in Raccoon Key
- B&B in Raccoon Key
- Vacation Homes in Raccoon Key
- Villas in Raccoon Key
- Resorts in Raccoon Key
- Apartments in Raccoon Key
- Stock Island Hotels
- Houseboats in Stock Island
- Fishing Resorts & in Stock Island
- Pet-friendly Hotels in Stock Island
- Condo Rentals in Stock Island
- Cottages in Stock Island
- Resorts in Stock Island
- Beach Hotels in Stock Island
- Vacation Homes in Stock Island
- 5 Star Hotels in Stock Island
- Boutique Hotels in Stock Island
- 4 Star Hotels in Stock Island
- Apartments in Stock Island
- Oceanfront Hotels in Stock Island
- RV Parks in Stock Island
- Luxury Hotels in Stock Island
- Guest Houses in Stock Island
- Hostels in Stock Island
- B&B in Stock Island
- Golf Hotels in Stock Island
- Condo Resorts in Stock Island
- Aparthotels in Stock Island
- Villas in Stock Island
- Resorts & Hotels with Spas in Stock Island
- Hotels with a Pool in Stock Island
- Hotels with an Outdoor Pool in Stock Island
- Hotels with Air Conditioning in Stock Island
- 3 Star Hotels in Stock Island
- Motels in Stock Island
- Hotels with Laundry Facilities in Stock Island
- Hotel Wedding Venues Hotels in Stock Island
- Hotels on the River in Stock Island
- Hotels & Resorts for Couples in Stock Island
- Family Hotels in Stock Island
- Hyatt Hotels in Stock Island
- Romantic Hotels in Stock Island
- Quiet Resorts & in Stock Island
- Hotels with Hot Tubs in Stock Island
- Hotels with Free Parking in Stock Island
- Hotels near Key West Golf Club
- Hotels near Robbie's
- Cow Key Hotels
- Houseboats in Cow Key
- Vacation Homes in Cow Key
- Condo Rentals in Cow Key
- Flights to Key West
- Flights to Big Coppitt Key
- Flights from Boca Chica Key
- Flights to Raccoon Key
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights to Stock Island
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Chicago to Stock Island
- Flights from Philadelphia to Stock Island
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Car rentals near Big Coppitt Key
- Car rentals near Stock Island Yacht Club & Marina
- Car rentals near Stock Island
- National Car Rental Rental Cars in Stock Island
- Enterprise Rental Cars in Stock Island
- Car rentals near Key West Golf Club
- Van Car Rentals near Key West Golf Club
- Mini Car Rentals near Key West Golf Club
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















