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Summerland Key Vacations

Pack those stellar shades. We have Summerland Key vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Summerland Key – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Summerland Key vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Summerland Key

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Summerland Key vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Summerland Key well.

Summerland Key Flight + Hotel packages

Top Hotel Deals

See all 61 Hotels in Summerland Key
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West
4.5 out of 5.0

Located in Stock Island, this hotel is 0.2 mi (0.4 km) from Key West Harbour and within 3 mi (5 km) of Robbie's and Key West Golf Club. Ernest Hemingway Home ...

$269

$269
Geiger Key Marina RV Park

Geiger Key Marina RV Park

5 Geiger Road, Key West
2.0 out of 5.0

Situated on the waterfront, this campground is within 9 mi (15 km) of Key West Golf Club, Key West Harbour, and Robbie's. Ernest Hemingway Home and Museum and ...

Parmer's Resort

Parmer's Resort

565 Barry Avenue, Little Torch Key
2.5 out of 5.0

Situated on the waterfront, this motel is within 9 mi (15 km) of Key West Visitors Center, Bahia Honda State Park and Beach, and Coupon Bight Aquatic Preserve. ...

Little Palm Island Resort & Spa - A Noble House Resort

Little Palm Island Resort & Spa - A Noble House Resort

28500 Overseas Hwy, Little Torch Key
5.0 out of 5.0

This adults-only Florida Keys resort occupies a 5-acre island 28 miles from Key West and offers private beachfront vacations without television or ...

The Perry Hotel Key West

The Perry Hotel Key West

7001 Shrimp Road, Key West
4.5 out of 5.0

Located in Stock Island, this resort is 1.3 mi (2.2 km) from Key West Harbour and 1.8 mi (2.8 km) from Key West Golf Club. Smathers Beach and Ernest Hemingway ...

$285

$285
Looe Key Reef Resort

Looe Key Reef Resort

27340 Overseas Highway, Ramrod Key
2.5 out of 5.0

Situated on the waterfront, this hotel is 4.1 mi (6.7 km) from Key West Visitors Center and within 12 mi (20 km) of Bahia Honda State Park and Beach and Coupon ...

Key West Harbour Oceanfront Suites

Key West Harbour Oceanfront Suites

6000 Peninsular Ave., Key West
4.0 out of 5.0

Offering direct access to the beach, this Stock Island condo building is within 3 mi (5 km) of Key West Harbour, Robbie's, and Key West Golf Club. Smathers Beach ...

$499

$499
Sugar Loaf Lodge

Sugar Loaf Lodge

17001 Overseas Hwy, Sugarloaf Key
3.0 out of 5.0

Situated on the waterfront, this hotel is within 16 mi (25 km) of Key West Golf Club, Key West Art and Historical Society, and Key West Harbour. Robbie's and ...

Hemingway Hideaway

Hemingway Hideaway

7 Coral Way, Key West
4.0 out of 5.0

Located in Stock Island, this vacation home is 1.1 mi (1.8 km) from Key West Harbour and 2.5 mi (4.1 km) from Key West Art and Historical Society. Robbie's and ...

Ed & Ellen's Lodging Big Pine Key

Ed & Ellen's Lodging Big Pine Key

1547 Narcissus Ave, Big Pine Key
3.5 out of 5.0

Situated in a rural location, this apartment building is 8.5 mi (13.7 km) from Bahia Honda State Park and Beach and within 32 mi (52 km) of Key West Golf Club ...

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.