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
waterfront cottage near key west, sleeps 6

waterfront cottage near key west, sleeps 6

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 cottage near key west, sleeps 6
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
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Blue Mind - Venture Out Unit 225

Blue Mind - Venture Out Unit 225

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.
Blue Mind - Venture Out Unit 225
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

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.
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Waterfront Cozy Cottage with Boat Ramp & Dock!

Waterfront Cozy Cottage with Boat Ramp & Dock!

Little Torch Key
When you stay at this cottage in Summerland Key, you'll be on the waterfront, within a 5-minute drive of National Key Deer Refuge Visitor Center and Big Pine ...
Waterfront Cozy Cottage with Boat Ramp & Dock!
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
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
HIDDEN HAMMOCK RESORT Palm cottage

HIDDEN HAMMOCK RESORT Palm cottage

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.
HIDDEN HAMMOCK RESORT Palm cottage
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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
38 Cottages
Lowest Price
AU$206
Highest Price
AU$236
Popular accommodation
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, waterfront cottage near key west, sleeps 6, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Blue Mind - Venture Out Unit 225, **TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool, Waterfront Cozy Cottage with Boat Ramp & Dock!, SEA SHELL COTTAGE UNIT #2, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, HIDDEN HAMMOCK RESORT Palm cottage

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$236 per night from 3 Dec to 4 Dec
AU$236
includes taxes & fees
3 Dec - 4 Dec
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
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$209 per night from 2 Dec to 3 Dec
AU$209
includes taxes & fees
2 Dec - 3 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
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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$206 per night from 5 Dec to 6 Dec
AU$206
includes taxes & fees
5 Dec - 6 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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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.