Summerland Key Holidays from AU$2,580
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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.
Ridley House - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was AU$4,446, price is now AU$2,580 per person
AU$2,580
per person
15 Feb - 21 Feb
found 1 day ago
Return flight included
Louisville (SDF) to Key West (EYW)
9.2/10 Wonderful! (845 reviews)
Room was clean, staff were awesome.
Reviewed on 27 Nov 2025
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was AU$5,746, price is now AU$3,030 per person
AU$3,030
per person
15 Feb - 21 Feb
found 1 day ago
Return flight included
Louisville (SDF) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Nice resort. Good food. Nice pool. Friendly staff.
Reviewed on 27 Nov 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was AU$5,657, price is now AU$2,987 per person
AU$2,987
per person
15 Feb - 21 Feb
found 1 day ago
Return flight included
Louisville (SDF) to Key West (EYW)
9.4/10 Exceptional! (390 reviews)
Everything was great. Staff were all super helpful.
Location fantastic.
Breakfast served outside the room on the verander we loved (the health shots were a lovely touch).
We had a great stay.
Would definitely recommend.
Reviewed on 22 Nov 2025
The Gardens Hotel
Old Town Key West
Save 100% on your flight
Price was AU$6,292, price is now AU$3,691 per person
AU$3,691
per person
15 Feb - 21 Feb
found 1 day ago
Return flight included
Louisville (SDF) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
Great breakfast, convenient location. Staff is very friendly. Rooms are nice and the garden area is pretty. I read all of the reviews and the hype around the place so it fell short of my expectations. If I had just gone there and not read the reviews I may have enjoyed it more. I would go back but I had stayed at places as nice or nice for my needs for what I believe to be better value. That being said I am glad I stayed there
Reviewed on 20 Nov 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$236 per night from 30 Nov to 1 Dec
AU$236
30 Nov - 1 Dec
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
We had a wonderful stay at Parmer's Resort. It was quiet and comfortable. We especially loved all the outdoor areas to sit and enjoy the views.
Reviewed on 23 Nov 2025
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 11 Dec to 12 Dec
AU$170
11 Dec - 12 Dec
includes taxes & fees
8/10 Very Good! (1,002 reviews)
View from the room was good. Close to key west too.
Reviewed on 21 Nov 2025
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
7.4/10 Good! (1,003 reviews)
Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect
Reviewed on 9 Nov 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$89
per adult
86% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
AU$185
per adult
98% 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.
