Hot Summerland Key Cottage Rates

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Featured Cottages in Summerland Key

Canal front, dockage, 2 bedroom,  2 bath

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Florida Keys Beaches and Venture Key ...
Opens in a new windowCanal front, dockage, 2 bedroom, 2 bath
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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

Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
Opens in a new windowPrivate Oceanfront Cottage with dockage, pool just minutes to Key West!
Charming cottages, dockage, pool, just minutes to Key West

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

Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Florida Keys Beaches and Upper ...
Opens in a new windowCharming cottages, dockage, pool, just minutes to Key West
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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 FL
Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
Opens in a new windowOld Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Venture Key are located ...
Opens in a new windowWonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Waterfront Home

Waterfront Home

Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy laundry facilities, tennis courts and a pool table. Popular attractions Florida Keys Beaches and Venture Key are ...
Opens in a new windowWaterfront 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 FL
Stay at this cottage in Summerland Key. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Opens in a new windowOld Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!

SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!

Summerland Key FL
Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Crab Key and Pye Key are located ...
Opens in a new windowSEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!
Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
Opens in a new windowCottage with Pool and Dockage, just minutes to Key West
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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
59 Cottages
Lowest Price
NZ$401
Highest Price
NZ$480
Popular accommodation
Canal front, dockage, 2 bedroom, 2 bath, Private Oceanfront Cottage with dockage, pool just minutes to Key West!, Charming cottages, dockage, pool, just minutes to Key West, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West., Waterfront Home, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!, Cottage with Pool and Dockage, just minutes to Key West

Top trending hotels in Summerland Key

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSugarloaf 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 NZ$401 per night from 29 Mar to 30 Mar
NZ$401
29 Mar - 30 Mar
includes taxes & fees
Stay at this beach motel in Summerland Key. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
Opens in a new windowParmer's 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
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowLooe 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 NZ$480 per night from 23 Mar to 24 Mar
NZ$480
23 Mar - 24 Mar
includes taxes & fees
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a marina. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSugar 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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.