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.
B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jun 27 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Miami (MIA)
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling on business? Take advantage of the business center, express check-out, and valet parking.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
per person
Jul 29 - Aug 3
found 19 hours ago
Roundtrip flight included
New York (JFK) to Miami (MIA)
An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A grocery/convenience store, a communal living room, and express check-out are also on offer.
Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
A full-service spa, 2 restaurants, and 3 outdoor pools are all featured at this luxury resort. Enjoy the gym and unwind at the bar/lounge and poolside bar.
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Save 100% on your flight
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this smoke-free hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and in-room childcare is an added bonus.
Sunrise in Miami Suites

Sunrise in Miami Suites

2 out of 5
South Beach
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
This hotel features free WiFi in public areas, a virtual front desk, and self parking. A communal living room and express check-out are also provided.

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
The price is $234 per night
$234
includes taxes & fees
$208 per night
May 7 - May 8
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
The price is $179 per night
$179
includes taxes & fees
$159 per night
May 7 - May 8
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
The price is $168 per night
$168
includes taxes & fees
$149 per night
Jun 1 - Jun 2
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
Cottage with Pool and Boat Dockage just minutes to Key West!

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

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

4/5(21 reviews)

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

Upper Sugarloaf Key

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