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.
Cavalier Hotel South Beach
South Beach
Price was $894, price is now $421 per person
$421
per person
Mar 23 - Mar 26
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.
Miami Downtown Condos
Downtown Miami
Price was $2,615, price is now $967 per person
$967
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Creekside Inn
Price was $2,144, price is now $881 per person
$881
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Casablanca Miami Beach
North Beach
Price was $1,067, price is now $495 per person
$495
per person
Apr 8 - Apr 14
found 13 hours ago
Roundtrip 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.
Solé Miami, A Noble House Resort
Ocean Four
Price was $1,100, price is now $518 per person
$518
per person
Mar 29 - Apr 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. 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 and an off-leash area. Enjoy the 24-hour gym and unwind at the beach bar and poolside bar.
Top Summerland Key hotels deals
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $158 total per night
$158 total
Jan 29 - Jan 30
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
Parmer's Resort
565 Barry Avenue Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$293 nightly
The price is $330 total per night
$330 total
Jan 22 - Jan 23
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
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
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $224 total per night
$224 total
Jan 22 - Jan 23
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!
Cudjoe Key FL
$286 nightly
The price is $317 total per night
$317 total
Jan 22 - Jan 23
Total with taxes and fees
This cottage features a garden, laundry facilities, and barbecue grills.
Pool
Kitchen
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 Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
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.
Frequently asked questions
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