Rockland Key Vacation Packages 2026 from $749

Rockland Key flight + hotel 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

$749

per person

Feb 27 - Mar 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli, concierge services, and barbecue grills are also on offer.

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,625

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a garden. Luggage storage and concierge services are also provided.

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$1,333

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. The restaurant provides options for dining, while the bar/lounge and poolside bar are great spots to unwind.

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight

$971

per person

Mar 5 - Mar 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit box and concierge services are also provided.

Pier House Resort & Spa

Key West Historic District

Save 100% on your flight

$2,023

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-in.

Top Rockland Key hotels deals

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$322 nightly

$363 total

Jan 19 - Jan 20

Total with taxes and fees

This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.

On private beach

Pool

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Free Cancellation

Reserve now, pay when you stay

$292 nightly

$329 total

Jan 4 - Jan 5

Total with taxes and fees

This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate the picnic area. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

Pool

Hot Tub

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue Key West FL

Free Cancellation

Reserve now, pay when you stay

$273 nightly

$307 total

Jan 11 - Jan 12

Total with taxes and fees

Pool

Pet friendly

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

$301 nightly

$338 total

Jan 4 - Jan 5

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd Key West FL

Free Cancellation

Reserve now, pay when you stay

$289 nightly

$325 total

Jan 4 - Jan 5

Total with taxes and fees

This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free beach shuttle.

Pool

Free airport shuttle

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Free Cancellation

$419 nightly

$472 total

Jan 26 - Jan 27

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.

Pool

Spa

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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.

Frequently asked questions

How much are vacation packages to Rockland Key?

If you like the idea of stress-free planning and big savings, our $749 Rockland Key vacation package will be just the ticket. With your flights and hotels sorted, organizing your getaway around this famous attraction is easier than ever.

Where can I get the best vacation package deals for Rockland Key?

You'll find an amazing range of Rockland Key package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties worldwide, crafting your ultimate vacation will be simple.

Why should I book my Rockland Key vacation bundle with Travelocity?

Because life is one incredible journey, and we have everything you could hope for to help you along the way. With our superb service and Price Match Guarantee, you can book with confidence. And you can sleep easy while you're away knowing we're always available to chat via our 24/7 support.