Hot Summerland Key Cottage Rates

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Featured Cottages in Summerland Key

Cottage with Pool  and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key
Stay at this cottage in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Cottage with Pool and Boat 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 NZ$499 per night from 19 Apr to 20 Apr
NZ$499
includes taxes & fees
19 Apr - 20 Apr
Stay at this cottage in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Private Oceanfront Cottage with 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
The price is NZ$585 per night from 1 May to 2 May
NZ$585
includes taxes & fees
1 May - 2 May
Stay at this cottage in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Cottage with Pool and Dockage, just minutes to Key West
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$604 per night from 20 Apr to 21 Apr
NZ$604
includes taxes & fees
20 Apr - 21 Apr
Stay at this cottage in Summerland Key. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
SEA SHELL COTTAGE UNIT #2 Sleeps 2

SEA SHELL COTTAGE UNIT #2 Sleeps 2

Summerland Key
Stay at this cottage in Summerland Key. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Crab Key and Pye Key are located ...
SEA SHELL COTTAGE UNIT #2 Sleeps 2
Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,

Little Torch Key
The price is NZ$691 per night from 21 Apr to 22 Apr
NZ$691
includes taxes & fees
21 Apr - 22 Apr
Book a stay at this beach cottage in Summerland Key. Enjoy a beach locale, a garden, and patios. Popular attractions Big Pine Key Flea Market and Blue Hole are ...
Direct Oceanfront Cottage-Sunrise View- #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
Stay at this cottage in Summerland Key. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Florida Keys Beaches and Upper ...
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
The price is NZ$614 per night from 27 Apr to 28 Apr
NZ$614
includes taxes & fees
27 Apr - 28 Apr
Stay at this cottage in Summerland Key. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Florida Keys Beaches and ...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Charming cottages, dockage, pool, just minutes to Key West

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

Cudjoe Key
The price is NZ$560 per night from 26 Apr to 27 Apr
NZ$560
includes taxes & fees
26 Apr - 27 Apr
Stay at this cottage in Summerland Key. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Florida Keys Beaches ...
Charming cottages, dockage, pool, 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
55 Cottages
Lowest Price
NZ$275
Highest Price
NZ$691
Popular accommodation
Cottage with Pool and Boat Dockage just minutes to Key West!, Private Oceanfront Cottage with dockage, pool just minutes to Key West!, Cottage with Pool and Dockage, just minutes to Key West, Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West, SEA SHELL COTTAGE UNIT #2 Sleeps 2, Direct Oceanfront Cottage-Sunrise View- #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, Charming cottages, dockage, pool, just minutes to Key West

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 NZ$275 per night from 13 May to 14 May
NZ$275
includes taxes & fees
13 May - 14 May
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the bar and the helpful staff in our reviews. ...
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
Stay at this 3-star hotel in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our ...
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 NZ$392 per night from 5 May to 6 May
NZ$392
includes taxes & fees
5 May - 6 May
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
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 NZ$300 per night from 1 May to 2 May
NZ$300
includes taxes & fees
1 May - 2 May
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Sugar Loaf Lodge
Don't see what you're looking for?
See all available properties in Summerland Key
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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.