Hot Summerland Key Cottage Rates

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Featured Cottages in Summerland Key

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West

Cudjoe Key
The price is AU$663 per night from 14 Mar to 15 Mar
AU$663
includes taxes & fees
14 Mar - 15 Mar
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.
Charming cottages, dockage, pool, just minutes to Key West
Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
With a stay at this cottage in Summerland Key, you'll be by the ocean, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Cottage with Pool and Dockage, just minutes to Key West
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cudjoe Key
The price is AU$611 per night from 29 Mar to 30 Mar
AU$611
includes taxes & fees
29 Mar - 30 Mar
With a stay at this cottage in Summerland Key, you'll be by the ocean, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
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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
Cottage with Pool  and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to 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.
Cottage with Pool and Boat Dockage just minutes to Key West!
SEA SHELL COTTAGE UNIT #2

SEA SHELL COTTAGE UNIT #2

Summerland Key
With a stay at this cottage in Summerland Key, you'll be within a 5-minute drive of Florida Keys Beaches and Crab Key.
SEA SHELL COTTAGE UNIT #2
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
The price is AU$712 per night from 16 Mar to 17 Mar
AU$712
includes taxes & fees
16 Mar - 17 Mar
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 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
Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,

Little Torch Key
The price is AU$663 per night from 28 Mar to 29 Mar
AU$663
includes taxes & fees
28 Mar - 29 Mar
A stay at this cottage places you in the heart of Summerland Key, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine Key Flea ...
Direct Oceanfront Cottage-Sunrise View- #2,
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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
46 Cottages
Lowest Price
AU$224
Highest Price
AU$712
Popular accommodation
Charming cottages, dockage, pool, just minutes to Key West, Cottage with Pool and Dockage, just minutes to Key West, Private Oceanfront Cottage with dockage, pool just minutes to Key West!, Waterfront Home, Cottage with Pool and Boat Dockage just minutes to Key West!, SEA SHELL COTTAGE UNIT #2, 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, Direct Oceanfront Cottage-Sunrise View- #2,

Top trending hotels in Summerland Key

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$224 per night from 24 Mar to 25 Mar
AU$224
includes taxes & fees
24 Mar - 25 Mar
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
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
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$513 per night from 7 Apr to 8 Apr
AU$513
includes taxes & fees
7 Apr - 8 Apr
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
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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$445 per night from 13 Mar to 14 Mar
AU$445
includes taxes & fees
13 Mar - 14 Mar
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
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.