Summerland Key Holidays from AU$952
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Your Summerland Key Holiday
Say bye-bye to planning worries and hello to a Summerland Key holiday package. With everything organised before you go, you can focus on discovering this city, starting with Breezeswept Beach Estates, which is good for adventure sports, fishing and watersports. Like to explore your new surroundings? Big Pine Key Flea Market, Cook Island and Blue Hole are some of the top places to visit during a trip to Summerland Key. That dream Summerland Key holiday is only clicks away. Browse accommodation, flights and more on Expedia for a trip that's tailored just for you.
The Latest Summerland Key Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
South Beach
Price was AU$1,450, price is now AU$952 per person
AU$952
per person
17 Dec - 21 Dec
found 5 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
The staff greeted us wonderfully. The room is clean. The VIP perk was pleasant. Would definitely stay here again.
Reviewed on 25 Sept 2025
President Hotel
South Beach
Price was AU$1,616, price is now AU$1,046 per person
AU$1,046
per person
17 Dec - 21 Dec
found 5 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8.4/10 Very Good! (1,825 reviews)
The room was good. Except no microwave and a lizard was in the room the first night and after calling front desk, and someone said he was coming up but my wife had to go down and get the guy. (He was asleep) after he did come in the room, my wife was the one who actually got the lizard. Mike, Henry, Kevon and the housekeeping staff were awesome ❤️❤️❤️💕
Reviewed on 8 Oct 2025
The Penguin Hotel
South Beach
Price was AU$1,472, price is now AU$980 per person
AU$980
per person
17 Dec - 21 Dec
found 5 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8.2/10 Very Good! (1,440 reviews)
Right on the beach, very vibrant area! Would stay here again.
Reviewed on 8 Oct 2025
Eden Roc Miami Beach
Mid Beach
Save 100% on your flight
Price was AU$2,126, price is now AU$1,421 per person
AU$1,421
per person
17 Dec - 21 Dec
found 5 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8.4/10 Very Good! (2,936 reviews)
Great resort! Great location. Multiple pools. Clean rooms, beautiful property. Staff always treats me so well. The concierge Joao really went above and beyond for me. He really made my trip special. Check in went very smoothly as well. Highly recommended!
Reviewed on 8 Oct 2025
Hotel Riu Plaza Miami Beach
Mid Beach
Save 100% on your flight
Price was AU$2,058, price is now AU$1,377 per person
AU$1,377
per person
17 Dec - 21 Dec
found 5 hours ago
Return direct flight included
Kansas City (MCI) to Miami (MIA)
8/10 Very Good! (1,102 reviews)
The one thing that I have to mention about this hotel is their water pressure. Almost all hotels have little water flow and little pressure. It is normal, but this only hotel got the biggest water flow. It was amazing to take a shower that was more comfortable than own home. I have never seen a hotel with the water flow. It was so comfortable
Reviewed on 4 Oct 2025
Our guide on where to stay in Summerland Key
Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about Summerland Key
Cutthroat Harbor Estates
While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Upper Sugarloaf Key.
Summerland Key Holiday
Summerland Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Max Temp Winter | 24ºC |
Max Temp Summer | 29ºC |
Top Sights | Bahia Honda State Park, Florida Keys Beaches and Calusa Beach |
Our pick of the best Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 9 Oct to 10 Oct
AU$225
9 Oct - 10 Oct
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Clean room , many options for guests to do around property. Close to key west and marathon"
Reviewed on 10 Sept 2025
Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 9 Oct to 10 Oct
AU$169
9 Oct - 10 Oct
includes taxes & fees
8/10 Very Good! (998 reviews)
"This was an excellent value for the price - the room was spacious and clean, the property was quiet. There was a beautiful view with a balcony. I could not have been happier with my experience!"
Reviewed on 6 Oct 2025
Looe Key Reef Resort
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$339 per night from 20 Oct to 21 Oct
AU$339
20 Oct - 21 Oct
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"This is a very REASONABLY priced lodging for the FL Keys so expect simple things. We had a great stay, room was clean, the young gent at the front desk was exceptionally friendly and helpful, ditto at checkout. The beds are comfortable. The shower head had great pressure and the onsite tiki bar is ..."
Reviewed on 15 Sept 2025
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.
What to do in Summerland Key
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
AU$84
per adult
86% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
AU$121
per traveller
92% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
