
Rockland Key Vacations from $1,412
Book a Hotel + Flight or Car together to unlock savings
The Latest Rockland Key vacation packages
Price found within the past 48 hours. Click for updated prices.

The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $2,481, price is now $1,412 per person
$1,412
per person
Feb 18 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
The hotel is wonderful and most of all free shuttle service to downtown. We really enjoyed our time there. Looking forward to visiting again!!
Reviewed on Dec 2, 2025

Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $3,664, price is now $1,956 per person
$1,956
per person
Feb 18 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The staff was courteous. The room was beautiful n spotless. But the refrigerators weren't working correctly n my food that I brought was spoiled. Ms. Gwendolyn, provided excellent service and Ms. Sophia, provided discount for my stayed. Also the showers needs to be repaired, it leaked when taking showers. Water was all over the floors, so we put towels on the floor to soak up the water. *At the restaurant Alex was an awesome server, highly recommend him*.
Reviewed on Dec 3, 2025


The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was $4,068, price is now $2,358 per person
$2,358
per person
Feb 18 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there
Reviewed on Nov 20, 2025

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $3,137, price is now $1,827 per person
$1,827
per person
Feb 18 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
Beautiful property, nice clean bungalows and great staff!
Reviewed on Dec 5, 2025
Don't see what you're looking for?
See all available trips from Singapore 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
$222 nightly
The price is $250 total per night from Dec 16 to Dec 17
$250 total
Dec 16 - Dec 17
Total with taxes and fees
8.6/10 Excellent! (1,734 reviews)
Staff very courteous! We arrived very early- hoping we could at least chk our bags before going to lunch ( 2 couples- booking two rooms). Our friends' room was already available .We were told ours would be ready soon. We had a lovely, long, leisurely lunch at Chicken Walk. Our room still wasnt ready ...
Reviewed on Dec 3, 2025

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $191 total per night from Dec 14 to Dec 15
$191 total
Dec 14 - Dec 15
Total with taxes and fees
8/10 Very Good! (1,747 reviews)
Grate stay...only thing is our room at the end of property a little far from the pool and breakfast bar. Next time will ask for a closer one.
Reviewed on Dec 3, 2025

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $227 total per night from Dec 8 to Dec 9
$227 total
Dec 8 - Dec 9
Total with taxes and fees
8.8/10 Excellent! (1,747 reviews)
Very nice clean and big room. Great view over the pools and harbor.
Reviewed on Dec 4, 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.


















