Deals on vacations and trips to Summerland Key
Save when you book Summerland Key package deals
Summerland Key flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Pelican Hotel
South Beach
Save 100% on your flight
Price was $1,271, price is now $648 per person
$648
per person
May 19 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Valet parking, a business center, and limo/town car service are also offered.
Casablanca Miami Beach
North Beach
Price was $9,627, price is now $3,795 per person
$3,795
per person
Jun 20 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
South Beach
Price was $12,663, price is now $6,418 per person
$6,418
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
South Beach
Save 100% on your flight
Price was $1,666, price is now $894 per person
$894
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features 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 a garden are also offered.
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,648, price is now $891 per person
$891
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Valet parking, a terrace, and express check-out are also offered.
Top Summerland Key hotels deals
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
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
565 Barry Avenue Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$207 nightly
The price is $232 total per night
$232 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
27340 Overseas Highway Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$256 nightly
The price is $288 total per night
$288 total
May 13 - May 14
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
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
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
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Frequently asked questions
Photos of local treasures
Browse Summerland Key vacation photos for more inspiration
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