Short-Term Rentals in Upper Sugarloaf Key, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Short-Term Rentals
  3.  USA

  4.  Florida
  5.  Sugarloaf Key
  6.  Upper Sugarloaf Key

Refine your search

Price per night

Amenity Filter

Rating

442 Best Short-Term Rentals in Upper Sugarloaf Key (Starting from $156)

Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages
House
Summerland Key, FL, USA
0.5k from Upper Sugarloaf Key center

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

20 Bedrooms12 Guests
9.0

Fabulous

314 reviews

$458
Average price / night
Check Availability
The Villa of Pelico Palms
The Villa of Pelico Palms
House
Monroe County, FL, 33042, United States
1.0k from Upper Sugarloaf Key center

AC, Arcade, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$1512
Average price / night
Check Availability
Pelico Paradise
Pelico Paradise
House
Upper Sugarloaf Key, Sugarloaf Key, Florida, USA
1.0k from Upper Sugarloaf Key center

Parking, Pet Friendly, Air Conditioner, Internet, Child Friendly

5 Bedrooms10 Guests
9.6

Exceptional

2 reviews

$304
Average price / night
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
Loggerhead Lagoon - Modern Waterfront Home
Loggerhead Lagoon - Modern Waterfront Home
House
Pirates Cove, FL, USA
1.5k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
New to Booking
$460
Average price / night
Check Availability
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning Views
House
18954 Acosta Trail Summerland Key Florida 33042 United States, Summerland Key, FL, 33042, United States
1.2k from Upper Sugarloaf Key center

Barbecue, Free Parking, Internet, Living Area, Outdoor Space

New to Booking
$744
Average price / night
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
Sublimely private luxury home with enveloping oceanfront views near Key West
Sublimely private luxury home with enveloping oceanfront views near Key West
House
Sugarloaf Key, FL, 33042, United States
1.3k from Upper Sugarloaf Key center

4 Bedrooms8 Guests
New to Booking
$2382
Average price / night
Check Availability
Unit 101
Unit 101
House
Cudjoe Key, FL, USA
3.3k from Upper Sugarloaf Key center

Security/Safety, Pool, Hot Tub, Wellness Facilities, Air Conditioner, View, Balcony/Terrace

5 Bedrooms6 Guests
New to Booking
$405
Average price / night
Check Availability
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
Check Availability
Waterfront Escape
Waterfront Escape
House
Upper Sugarloaf Key, FL, 33042, United States
1.5k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, No Smoking, TV, Washer

3 Bedrooms6 Guests
New to Booking
$317
Average price / night
Check Availability
Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
4.1k from Upper Sugarloaf Key center

Accommodations, Pools, Parking, Lodges, Cabins, Lodgings, Places to stay, Accessible hotels

13 Bedrooms10 Guests
7.4

Good

552 reviews

$313
Average price / night
Check Availability
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
Check Availability
Key Lime Time
Key Lime Time
House
Cudjoe Key, FL, USA
4.5k from Upper Sugarloaf Key center

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

4 Bedrooms12 Guests
New to Booking
$363
Average price / night
Check Availability
Slice of Paradise
Slice of Paradise
House
Cudjoe Key, FL, 33042, United States
1.8k from Upper Sugarloaf Key center

AC, Dryer, Internet, Laundry, No Smoking, Washer

2 Bedrooms6 Guests
New to Booking
$288
Average price / night
Check Availability
Parrotfish Pointe
Parrotfish Pointe
House
Cudjoe Key, FL, USA
4.8k from Upper Sugarloaf Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

3 Bedrooms6 Guests
New to Booking
$301
Average price / night
Check Availability
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
Check Availability
3-bedroom waterfront house in fabulous Cudjoe Key
3-bedroom waterfront house in fabulous Cudjoe Key
House
Cudjoe Key, FL, 33042, United States
1.8k from Upper Sugarloaf Key center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$357
Average price / night
Check Availability
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
Check Availability
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
Check Availability
Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly!
Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly!
House
Cudjoe Key, FL, 33042, United States
1.9k from Upper Sugarloaf Key center

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

3 Bedrooms6 Guests
8.6

Fabulous

4 reviews

$321
Average price / night
Check Availability
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
Check Availability
Secluded Jungle Paradise
Secluded Jungle Paradise
House
Summerland Key, FL, 33042, United States
2.0k from Upper Sugarloaf Key center

AC, Dryer, Internet, Laundry, No Smoking, Washer

4 Bedrooms8 Guests
New to Booking
$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 Short-Term Rentals in Upper Sugarloaf Key.

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

Upper Sugarloaf Key Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 442 verified short-term rentals in Upper Sugarloaf Key, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Upper Sugarloaf Key vary depending on location, property size, and travel dates. Rates typically start from around $156 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Upper Sugarloaf Key include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Upper Sugarloaf Key, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Upper Sugarloaf Key often include amenities such as Laundry, View, and Balcony/Terrace, providing a comfortable and convenient stay.

Short-term rentals in Upper Sugarloaf Key are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.