Rockland Key Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Rockland Key vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.0-star property
The Key West Hotel
Key West Historic District
9.2/10 Wonderful! (562 reviews)
Oct 10 - Oct 12
2 night stay
Hartford (BDL) to Key West (EYW)
Breeze Airways • Coach
Key West (EYW) to Hartford (BDL)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,347, price is now $944 per person
$944
per person
found 12 hours ago
Great place to stay - highly recommend.
Reviewed on Aug 20, 2026
3.0-star property
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
9.4/10 Exceptional! (3 reviews)
Nov 11 - Nov 17
6 night stay
Hartford (BDL) to Key West (EYW)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,605, price is now $1,928 per person
$1,928
per person
found 8 hours ago
Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location .
Reviewed on Mar 26, 2026
3.5-star property
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Old Town Key West
8.8/10 Excellent! (3 reviews)
Oct 13 - Oct 18
5 night stay
New York (NYC) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,307, price is now $2,459 per person
$2,459
per person
found 1 day ago
The location to the things we wanted to do was perfect
Reviewed on May 1, 2026
2.0-star property
Bananas Foster by Brightwild Epic Guesthouse
Key West Historic District
No reviews
Dec 3 - Dec 8
5 night stay
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
American Airlines • Coach
Key West (EYW) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Coach
Save 100% on your flight
Price was $12,111, price is now $9,012 per person
$9,012
per person
found 1 day ago
3.5-star property
Paradise Inn Key West - Adults Only
Old Town Key West
9.2/10 Wonderful! (1,005 reviews)
Nov 10 - Nov 14
4 night stay
Hartford (BDL) to Key West (EYW)
American Airlines • Non-stop roundtrip • Coach
Price was $1,537, price is now $1,144 per person
$1,144
per person
found 1 day ago
Loved our stay!
Reviewed on Sep 8, 2026
Top rated hotels for your Rockland Key vacation package
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
Reserve now, pay when you stay
8.14 mi from city center
$210 nightly
The price is $237 total per night
$237 total
Sep 15 - Sep 16
Total with taxes and fees
Guests of Southernmost Beach Resort and Guesthouses have access to a full-service spa, 3 outdoor pools, and a gym. Self parking is offered for USD 53.75 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this spa hotel include conference space, coffee/tea in a common area, and a computer station.
Pool
Spa
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
5.04 mi from city center
$188 nightly
The price is $212 total per night
$212 total
Sep 10 - Sep 11
Total with taxes and fees
Guests of Beachside Resort & Residences have access to a private beach, a marina, and an outdoor pool. If you drive, self parking is USD 25.00 per night, and there's also a free area shuttle. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and concierge services. Other amenities at this beach hotel include a 24-hour gym, free WiFi in public areas, and a hot tub.
On private beach
Pool
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
5.16 mi from city center
$160 nightly
The price is $180 total per night
$180 total
Sep 10 - Sep 11
Total with taxes and fees
Blue Flamingo Resort Key West features 2 outdoor pools, karaoke, and a 24-hour gym. If you drive, self parking is USD 15.00 per night, and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Other amenities at this family-friendly hotel include free WiFi in public areas, a hot tub, and meeting rooms.
Pool
Hot Tub
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.
Explore More Ways to Travel with Travelocity
- B&B in Stock Island
- Condo Rentals in Stock Island
- Adventure Hotels in Stock Island
- Hotels with Hot Tubs in Stock Island
- Stock Island Hotels
- Houseboats in Stock Island
- Vacation Homes in Stock Island
- Rv Parks in Stock Island
- Resorts in Stock Island
- Condo Rentals in Raccoon Key
- Raccoon Key Hotels
- Houseboats in Raccoon Key
- Vacation Homes in Raccoon Key
- 5 Star Hotels in Boca Chica Key
- Cheap Hotels in Boca Chica Key
- Boca Chica Key Hotels
- Geiger Key Hotels
- 5 Star Hotels in Big Coppitt Key
- Big Coppitt Key Hotels
- Houseboats in Big Coppitt Key
- Resorts in Big Coppitt Key
- All Inclusive Resorts & in Key West
- Beach Resorts & in Key West
- Cheap Hotels in Key West
- Key West Hotels
- Houseboats in Key West
- Apartments in Key Haven
- Vacation Homes in Key Haven
- Hotels near Stock Island Yacht Club & Marina
- Flights from Boston to Stock Island
- Flights from Charlotte to Stock Island
- Flights from New York to Stock Island
- Flights from Philadelphia to Stock Island
- Flights from Raleigh to Stock Island
- Flights from Charleston to Stock Island
- Flights from Myrtle Beach to Stock Island
- Flights from Fort Lauderdale to Stock Island
- Flights from Fort Myers to Stock Island
- Flights from Huntsville to Stock Island
- Flights from Raccoon Key
- Flights from Milwaukee to Raccoon Key
- Flights from Dallas to Boca Chica Key
- Flights from New York to Boca Chica Key
- Flights from Boca Chica Key
- Flights from Newark to Boca Chica Key
- Flights from Tampa to Boca Chica Key
- Flights from Key West Intl.
- Flights from Big Coppitt Key
- Flights to Key West
- Flights from Miami to Key West
- Flights from Orlando to Key West
- Flights from Tampa to Key West
- Flights from Columbus to Key Haven
- Flights from Kansas City to Key Haven
- Flights from Nashville to Key Haven
- Flights from New Orleans to Key Haven
- Flights from St. Louis to Key Haven
- Flights from Richmond to Key Haven
- Flights from Milwaukee to Key Haven
- Flights from Rochester to Key Haven
- Flights from Grand Rapids to Key Haven
- National Key Deer Refuge Visitor Center
- Ramrod Key Vacations
- Little Torch Key Vacations
- Fleming Key Vacations
- Florida Keys Eco - Discovery Center
- Fort Zachary Taylor Historic State Park
- Stock Island Vacations
- Sugarloaf Key Vacations
- San Carlos Institute - Casa Cuba
- Crane Point Museum and Nature Center
- Raccoon Key Vacations
- Dredgers Key Vacations
- Marathon Vacations
- Mlk Community Pool & Community Center
- Coupon Bight Aquatic Preserve
- Ernest Hemingway Home and Museum
- Donkey Milk House
- Southernmost Point
- Key West Butterfly and Nature Conservatory
- Key West Tropical Forest and Botanical Garden
- Bahia Honda Key Vacations
- Sails To Rails Museum at Flagler Station
- Key West Vacations
- All inclusive Vacation Packages Key West
- Blue Hole
- The Kite House
- Smathers Beach
- Big Pine Key Vacations
- Cudjoe Key Vacations
- Fort East Martello Museum and Gallery
- Duval Street
