Hot Summerland Key Cottage Rates

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Featured Cottages in Summerland Key

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
ISLE BE BACK To The Sunny Keys

ISLE BE BACK To The Sunny Keys

Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be by the sea, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
ISLE BE BACK To The Sunny Keys
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Waterfront Home

Waterfront Home

Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Waterfront Home
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Riley's Retreat - Venture Out 107

Riley's Retreat - Venture Out 107

Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Venture Key.
Riley's Retreat - Venture Out 107
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4

Summerland Key
With a stay at this cottage in Summerland Key, you'll be by the sea, within a 5-minute drive of Florida Keys Beaches and Crab Key.
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Truly sitting right on the ocean. Ocean's Edge has forever ocean views.

Truly sitting right on the ocean. Ocean's Edge has forever ocean views.

2 out of 5
Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Truly sitting right on the ocean. Ocean's Edge has forever ocean views.
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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.

Summerland Key Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Summerland Key will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Summerland Key definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Summerland Key, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Summerland Key Cottages essential information

Accommodation
39 Cottages
Lowest Price
AU$322
Highest Price
AU$540
Popular accommodation
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, ISLE BE BACK To The Sunny Keys, Waterfront Home, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Riley's Retreat - Venture Out 107, THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Truly sitting right on the ocean. Ocean's Edge has forever ocean views.

Top trending hotels in Summerland Key

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$540 per night from 4 Jan to 5 Jan
AU$540
includes taxes & fees
4 Jan - 5 Jan 2025
With a stay at Parmer's Resort in Summerland Key, you'll be on the waterfront, within a 15-minute drive of Florida Keys Beaches and National Key Deer Refuge ...
Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939, Summerland Key, FL
With a stay at Sugarloaf Key Hotel at KOA Resort in Summerland Key, you'll be 7.2 mi (11.5 km) from Florida Keys Beaches and 16.2 mi (26.1 km) from Florida Keys ...
Sugarloaf Key Hotel at KOA Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$322 per night from 23 Dec to 24 Dec
AU$322
includes taxes & fees
23 Dec - 24 Dec
With a stay at Sugar Loaf Lodge in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Sound.
Sugar Loaf Lodge
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Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is AU$385 per night from 24 Dec to 25 Dec
AU$385
includes taxes & fees
24 Dec - 25 Dec
Located in Summerland Key, Looe Key Reef Resort is by the ocean, a 4-minute drive from Florida Keys Beaches and 5 minutes from National Key Deer Refuge Visitor ...
Looe Key Reef Resort
Don't see what you're looking for?
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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.

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^Subject to availability and chosen travel dates.