Cottage Rentals in Upper Sugarloaf Key, FL: Compare 10+ Sites & Save

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  4.  Florida

  5.  Sugarloaf Key

  6.  Upper Sugarloaf Key

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41 Best Cottage Rentals in Upper Sugarloaf Key (Starting from $210)

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
Cottage
Cudjoe Key, FL, 33042, United States
2.6k from Upper Sugarloaf Key center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.0

Fabulous

57 reviews

$286
Average price / night
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Cottage with Pool  and Boat Dockage just minutes to Key West!
Cottage with Pool and Boat Dockage just minutes to Key West!
Cottage
Cudjoe Key, FL, 33042, United States
3.0k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
8.6

Fabulous

162 reviews

$210
Average price / night
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Cottage with Pool and Dockage, just minutes to Key West
Cottage with Pool and Dockage, just minutes to Key West
Cottage
Cudjoe Key, FL, 33042, United States
3.1k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.2

Superb

167 reviews

$383
Average price / night
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Quaint cottage, pool, dockage just minutes to Key West!
Quaint cottage, pool, dockage just minutes to Key West!
Cottage
Cudjoe Key, FL, 33042, United States
3.1k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.0

Fabulous

151 reviews

$301
Average price / night
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Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cottage
Cudjoe Key, FL, 33042, United States
3.1k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
8.6

Fabulous

166 reviews

$217
Average price / night
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Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with swimming pool and dockage, just minutes to Key West!
Cottage
Cudjoe Key, FL, 33042, United States
3.1k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
9.0

Fabulous

168 reviews

$234
Average price / night
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Charming cottages, dockage, pool, just minutes to Key West
Charming cottages, dockage, pool, just minutes to Key West
Cottage
Cudjoe Key, FL, 33042, United States
3.2k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
8.6

Fabulous

126 reviews

$290
Average price / night
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Canal front, dockage, 2 bedroom,  2 bath
Canal front, dockage, 2 bedroom, 2 bath
Cottage
Cudjoe Key, FL, 33042, United States
5.0k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
8.8

Fabulous

96 reviews

$351
Average price / night
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Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Ocean view home -Private launch & breath taking sunset views-min 28 day rentals
Cottage
Cudjoe Key, FL, 33042, United States
5.1k from Upper Sugarloaf Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

24 reviews

$215
Average price / night
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NAUTILUS...ocean front cottage retreat ~
NAUTILUS...ocean front cottage retreat ~
Cottage
Cudjoe Key, FL, 33042, United States
5.2k from Upper Sugarloaf Key center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
8.8

Fabulous

6 reviews

$600
Average price / night
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Waterfront Home
Waterfront Home
Cottage
Cudjoe Key, FL, 33042, United States
5.3k from Upper Sugarloaf Key center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
8.8

Fabulous

179 reviews

$311
Average price / night
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A slice of paradise
A slice of paradise
Cottage
Cudjoe Key, FL, 33042, United States
5.3k from Upper Sugarloaf Key center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.0

Fabulous

98 reviews

$270
Average price / night
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waterfront cottage near key west, sleeps 6
waterfront cottage near key west, sleeps 6
Cottage
Cudjoe Key, FL, 33042, United States
5.3k from Upper Sugarloaf Key center

AC, Arcade, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
9.4

Superb

28 reviews

$307
Average price / night
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water at your back door
water at your back door
Cottage
Cudjoe Key, FL, 33042, United States
5.3k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
8.8

Fabulous

34 reviews

$358
Average price / night
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Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Cottage
Cudjoe Key, FL, 33042, United States
5.3k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
10.0

Exceptional

37 reviews

$255
Average price / night
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Beautiful Cottage & Amenities in Gated Community
Beautiful Cottage & Amenities in Gated Community
Cottage
Cudjoe Key, FL, 33042, United States
5.4k from Upper Sugarloaf Key center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$788
Average price / night
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Cozy, Perfect Conch Cottage! - VO315
Cozy, Perfect Conch Cottage! - VO315
Cottage
Summerland Key, FL, 33042, United States
5.4k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.2

Superb

33 reviews

$268
Average price / night
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Canal front with open water views in Venture Out - Lot 529
Canal front with open water views in Venture Out - Lot 529
Cottage
Cudjoe Key, FL, 33042, United States
5.4k from Upper Sugarloaf Key center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$376
Average price / night
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35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Cottage
CUDJOE KEY, FL, 33042, United States
5.4k from Upper Sugarloaf Key center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms6 Guests
9.8

Exceptional

132 reviews

$420
Average price / night
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Fishermen’s Paradise
Fishermen’s Paradise
Cottage
Cudjoe Key, FL, 33042, United States
5.4k from Upper Sugarloaf Key center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.2

Superb

99 reviews

$287
Average price / night
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Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cottage
Cudjoe Key, FL, 33042, United States
5.4k from Upper Sugarloaf Key center

AC, Balcony, Barbecue, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
9.6

Exceptional

14 reviews

$362
Average price / night
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ISLE BE BACK To The Sunny Keys
ISLE BE BACK To The Sunny Keys
Cottage
Cudjoe Key, FL, 33042, United States
5.4k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.6

Exceptional

33 reviews

$236
Average price / night
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Breezy Point - Venture Out Unit 199
Breezy Point - Venture Out Unit 199
Cottage
Cudjoe Key, FL, 33042, United States
5.5k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$294
Average price / night
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**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Cottage
Cudjoe Key, FL, 33042, United States
5.5k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

217 reviews

$464
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Cottage Rentals in Upper Sugarloaf Key.

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Upper Sugarloaf Key Cottage Rentals on the Map

Frequently Asked Questions

You can explore 41 verified cottage rentals in Upper Sugarloaf Key. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Upper Sugarloaf Key vary based on the season, location, and amenities offered. Rates typically start from around $210 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Upper Sugarloaf Key feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 18 listings in Upper Sugarloaf Key welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Upper Sugarloaf Key are known for their comfort and charm, often including amenities such as Kitchen, Laundry, and Bedding/Linens. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Upper Sugarloaf Key are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.