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

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  3.  USA

  4.  Florida

  5.  Sugarloaf Key
  6.  Upper Sugarloaf Key

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31 Beach Home Rentals in Upper Sugarloaf Key (Starting from $156)

Villa of the Setting Sun
Villa of the Setting Sun
House
Upper Sugarloaf Key, Sugarloaf Key, Florida, USA
1.3k from Upper Sugarloaf Key center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

4 Bedrooms8 Guests
8.0

Good

1 reviews

$2804
Average price / night
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Villa and Bungalow of Pelico Palms
Villa and Bungalow of Pelico Palms
Villa
Monroe County, FL, 33042, United States
1.0k from Upper Sugarloaf Key center

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

6 Bedrooms14 Guests
New to Booking
$1751
Average price / night
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Newly built home in Cudjoe Key
Newly built home in Cudjoe Key
House
Cudjoe Key, FL, USA
2.2k from Upper Sugarloaf Key center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms7 Guests
New to Booking
$583
Average price / night
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Pelico Palms Estate.
Pelico Palms Estate.
House
Monroe County, FL, 33042, United States
1.0k from Upper Sugarloaf Key center

AC, Arcade, Balcony, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area

9 Bedrooms20 Guests
9.8

Exceptional

7 reviews

$3053
Average price / night
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Tranquility in Paradise - Cudjoe
Tranquility in Paradise - Cudjoe
House
Summerland Key, FL, USA
2.3k from Upper Sugarloaf Key center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
New to Booking
$156
Average price / night
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Private Pool Oasis — 3 King Suites | 30 Min to Key West
Private Pool Oasis — 3 King Suites | 30 Min to Key West
House
Monroe County, FL, 33042, United States
1.1k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
7.6

Good

5 reviews

$945
Average price / night
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Ocean View with Pool, 4 bedroom Vila Near Key West
Ocean View with Pool, 4 bedroom Vila Near Key West
Villa
Cudjoe Key, FL, USA
2.7k from Upper Sugarloaf Key center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$810
Average price / night
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Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning Views
House
Summerland Key, FL, 33042, United States
1.2k from Upper Sugarloaf Key center

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

1 Bedroom4 Guests
New to Booking
$692
Average price / night
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Waterfront, Pet Friendly - Loggerhead Lagoon
Waterfront, Pet Friendly - Loggerhead Lagoon
House
Sugarloaf Key, FL, 33042, United States
1.5k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
New to Booking
$336
Average price / night
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CUDJOE GARDENS SANCTUARY- 3 BED/ 2 BATH- POOL, SPA, RV HOOK UP, BRING YOUR BOAT
CUDJOE GARDENS SANCTUARY- 3 BED/ 2 BATH- POOL, SPA, RV HOOK UP, BRING YOUR BOAT
House
Cudjoe Key, FL, 33042, United States
1.7k from Upper Sugarloaf Key center

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

3 Bedrooms6 Guests
New to Booking
$486
Average price / night
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3 Bedroom/2 Bath Canal Home w/ Private Pool and Large Concrete Dock- Cudjoe Key
3 Bedroom/2 Bath Canal Home w/ Private Pool and Large Concrete Dock- Cudjoe Key
House
Cudjoe Key, FL, 33042, United States
1.8k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
New to Booking
$424
Average price / night
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Waterfront home with a large dock, pool, and deck area. Can accommodate pets.
Waterfront home with a large dock, pool, and deck area. Can accommodate pets.
House
Summerland, FL, 33042, United States
1.8k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$412
Average price / night
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Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
House
Upper Sugarloaf Key, FL, 33042, United States
1.9k from Upper Sugarloaf Key center

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

4 Bedrooms12 Guests
9.2

Superb

7 reviews

$534
Average price / night
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Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe
Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe
House
Summerland Key, FL, 33042, United States
2.0k from Upper Sugarloaf Key center

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

3 Bedrooms6 Guests
9.6

Exceptional

24 reviews

$336
Average price / night
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Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool
Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool
House
Cudjoe Key, FL, 33042, United States
2.2k from Upper Sugarloaf Key center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fireplace, Free Parking, Heater

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$499
Average price / night
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Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool
Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool
House
Cudjoe Key, FL, 33042, United States
2.3k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$393
Average price / night
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Oceanside, pet friendly, smart home with plenty of paddle equipment
Oceanside, pet friendly, smart home with plenty of paddle equipment
House
Cudjoe Key, FL, 33042, United States
2.3k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
9.6

Exceptional

29 reviews

$214
Average price / night
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Private Secluded Ocean View & Pool Near Key West
Private Secluded Ocean View & Pool Near Key West
House
Summerland Key, FL, 33042, United States
2.3k from Upper Sugarloaf Key center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms10 Guests
8.0

Good

103 reviews

$750
Average price / night
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Private Beach House w/Pool
Private Beach House w/Pool
House
Cudjoe Key, FL, 33042, United States
2.3k from Upper Sugarloaf Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$881
Average price / night
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Magnificent Ocean views, privacy abounds on this well appointed mini estate.
Magnificent Ocean views, privacy abounds on this well appointed mini estate.
House
Cudjoe Key, FL, 33042, United States
2.4k from Upper Sugarloaf Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$532
Average price / night
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3/2  Cudjoe Key waterfront single level house.
3/2 Cudjoe Key waterfront single level house.
House
Cudjoe Key, FL, 33042, United States
2.4k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$431
Average price / night
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Upscale Canal-Front Escape w/ Private Pool, Dock & Water Views
Upscale Canal-Front Escape w/ Private Pool, Dock & Water Views
House
Cudjoe Key, FL, 33042, United States
2.5k from Upper Sugarloaf Key center

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

3 Bedrooms6 Guests
New to Booking
$341
Average price / night
Check Availability
Fisherman's Paradise
Fisherman's Paradise
House
Cudjoe Key, FL, 33042, United States
2.5k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$884
Average price / night
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Villa Jekjak
Villa Jekjak
House
Summerland Key, FL, 33042, United States
2.5k from Upper Sugarloaf Key center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$407
Average price / night
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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
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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Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with Pool
Villa
125 Colson Dr, Summerland Key, FL, 33042, United States
2.7k from Upper Sugarloaf Key center

Barbecue, Business Services, Free Parking, Hot Tub, Internet, Kids Pool, Laundry, Living Area, No Smoking

10.0

Exceptional

2 reviews

$1096
Average price / night
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Beachfront • Heated Pool • Hot Tub • Oceanview
Beachfront • Heated Pool • Hot Tub • Oceanview
Villa
Cudjoe Key, FL, 33042, United States
2.7k from Upper Sugarloaf Key center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$947
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 Beach Rentals in Upper Sugarloaf Key.

Where to stay in Upper Sugarloaf Key? Best neighborhoods & areas

Upper Sugarloaf Key Beach Rentals on the Map

Frequently Asked Questions

You can explore 31 verified beach rentals in Upper Sugarloaf Key. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Upper Sugarloaf Key vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $156 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Upper Sugarloaf Key offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Upper Sugarloaf Key welcome pets. Currently, 19 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Upper Sugarloaf Key often include amenities designed for coastal living, such as Ocean View, View, and Laundry. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.