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.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was $942, price is now $428 per person
$428
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.
Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was $2,233, price is now $609 per person
$609
per person
Jun 20 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This smoke-free condo includes 2 restaurants, an outdoor pool, and a 24-hour gym. Business travelers can take advantage of the business center. A poolside bar, a 24-hour front desk, and a coffee shop are also provided.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $4,303, price is now $1,759 per person
$1,759
per person
Jun 6 - Jun 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.
The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $15,727, price is now $8,370 per person
$8,370
per person
Jun 14 - Jun 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This aparthotel features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Save 100% on your flight
Price was $1,223, price is now $660 per person
$660
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like full breakfast and WiFi in public areas. Valet parking, a terrace, and luggage storage are also offered.

Top Summerland Key hotels deals

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
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
$238 nightly
The price is $268 total per night
$268 total
Apr 27 - Apr 28
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
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
$217 nightly
The price is $245 total per night
$245 total
May 3 - May 4
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A picnic area is also provided.
Pool
Pet friendly
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
$169 nightly
The price is $190 total per night
$190 total
May 3 - May 4
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
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key FL
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
Modern Canal-Front Home with 35' Seawall, Bikes, Grill & Community Amenities

Modern Canal-Front Home with 35' Seawall, Bikes, Grill & Community Amenities

Cudjoe Key FL
Get rates
A hot tub is featured at this vacation home, along with barbecue grills.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Summerland Key
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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

Sugarloaf Beach

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

Upper Sugarloaf Sound

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

Upper Sugarloaf Sound

Frequently asked questions

How much are vacation packages to Summerland Key?
With deals starting as low as $428, 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

View To Old Bahia Honda Bridge, Part Of The Florida Keys Overseas Heritage Trails, From West Summerland Key On A Sunny Autumn Day With A Clear Blue Sky And A Few Clouds
Aerial view of overseas highway and bridge road surrounded by blue water and the Gulf of Mexico, Summerland Key, United States.
Aerial view of road and bridge over turquoise water along the coastline, Summerland Key, Florida, United States.
Aerial view of road to Key West with turquoise water and small island, Summerland Key, Florida, United States.
Mom and baby dolphin playing in the wake of a boat

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