Deals on vacations and trips to Summerland Key

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Summerland Key flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Beach Place Hotel

Beach Place Hotel

2 out of 5
North Beach
Save 100% on your flight
Price was $570, price is now $297 per person
$297
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
An outdoor pool, free self parking, and laundry facilities are featured at this hotel. There's a garden and multilingual staff can provide around-the-clock assistance.
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was $1,030, price is now $503 per person
$503
per person
Nov 9 - Nov 14
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This historic resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.
Ridley House - Key West Historic Inns

Ridley House - Key West Historic Inns

3.5 out of 5
Key West Historic District
Price was $1,972, price is now $966 per person
$966
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and luggage storage. Enjoy the free buffet breakfast each morning. Concierge services are provided for your convenience.
RS Boutique Suites - Miami

RS Boutique Suites - Miami

4.5 out of 5
Downtown Miami
Save 100% on your flight
Price was $829, price is now $446 per person
$446
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This condo features an outdoor pool and a gym. Enjoy the hot tub and perks like free WiFi. You'll appreciate the sauna, poolside bar, and laundry facilities.
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
Price was $1,582, price is now $852 per person
$852
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Key West (EYW)
This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Self parking, a garden, and luggage storage are also offered.

Top Summerland Key hotels deals

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue, Summerland Key, FL
Free Cancellation
Reserve now, pay when you stay
$148 nightly
The price is $167 total per night
$167 total
Sep 28 - Sep 29
Total with taxes and fees
The private beach and marina are among the highlights at this motel. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Enjoy the outdoor pool and free perks like on-the-go breakfast and free self parking.
On private beach
Pool
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $111 total per night
$111 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features a marina, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free WiFi. A bar/lounge and a garden are also provided.
Pool
Parking included
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $125 total per night
$125 total
Sep 28 - Sep 29
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-in, and luggage storage are also on offer.
Pool
Pet friendly
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939, Summerland Key, FL
Get rates
The private beach and marina are among the highlights at this hotel. Enjoy the outdoor pool and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
On private beach
Pool
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Get rates
This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,

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This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
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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.

Popular places to visit

Upper Sugarloaf Sound

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

Upper Sugarloaf Sound

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

Sugarloaf Beach

Upper Sugarloaf Key

Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.

Upper Sugarloaf Key

Frequently asked questions

How much are vacation packages to Summerland Key?
With deals starting as low as $297, flight and hotel packages are a fantastic way to make your budget stretch further. Summerland Key, here you come!
Where can I get the best vacation package deals for Summerland Key?
With around 400 air carriers and 1,000,000 hotels across the world, it's hard to top Travelocity. Take advantage of our impressive range and create your dream Summerland Key package deal. Don't you love it when vacation planning is that easy?
Why should I purchase my Summerland Key vacation bundle with Travelocity?
You'll not only save lots, but you'll also have access to our 24/7 customer support, high-quality service and a Price Match Guarantee. Wander across the world, uncover lesser-known sights and make lifelong memories — we'll take care of the little details.
Can I save money on my Summerland Key car rental if I book it with a hotel or flight?
With a Summerland Key vacation package, you can combine your car, flight and hotel bookings and save a tidy sum. If you're eager to explore the best of this fantastic location, why not make tracks to PortMiami? This famous attraction is 110 mi from Summerland Key. With your own rental car, you'll be there belong long.
What is the best time of year to go to Summerland Key?
If you'd rather avoid expensive airfares, hordes of tourists and packed hotels, organize your trip outside of January, February and March. The quietest time to visit Summerland Key is August, September and October. You'll find hotel rates are the highest in and the most economical in .
Which airport is best for Summerland Key?
The top airport for Summerland Key is Key West Intl. Airport (EYW). You'll find it 20 mi east of the downtown area.
Where should I stay when visiting Summerland Key?
If you're after someplace comfortable to base yourself, check out the Tropical Island Sanctuary. It's the top choice for many travelers.

Photos of local treasures

Browse Summerland Key vacation photos for more inspiration

Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house
Sugarloaf Shores featuring a sunset and tropical scenes
Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house