244+ Private Villas and Holiday Rentals in Upper Sugarloaf Key |
Upper Sugarloaf Key Holiday Rentals
New
- Sugarloaf Key
- Sugarloaf Shores
- 0.66 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
House
- Air Conditioner
- Internet
- Laundry
CA $1,634/Night
For 7 Nights CA $11,440
10.0
Exceptional
(4 Reviews)
2798.62 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Villa
- Private Beach
- Oceanfront
- Hot Tub
CA $1,109/Night
For 7 Nights CA $7,765
10.0
Exceptional
(2 Reviews)
- Florida
- Cudjoe Key
- 0.70 mi to center
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
CA $1,501/Night
For 7 Nights CA $10,504
10.0
Exceptional
(233 Reviews)
- Florida
- Cudjoe Key
- 0.59 mi to center
1200 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
CA $685/Night
For 7 Nights CA $4,794
9.6
Exceptional
(2 Reviews)
2228.13 ft²
10 Guests
5 Bedrooms
4 Bathrooms
House
- Pet Friendly
- Parking
- Air Conditioner
CA $416/Night
For 7 Nights CA $2,911
New
- Florida
- Sugarloaf Key
- 1.35 mi to center
1 Bedroom
1 Bathroom
Couples Retreat
House
- Balcony/Terrace
- Pet Friendly
- Parking
CA $1,267/Night
For 7 Nights CA $8,871
10.0
Exceptional
(209 Reviews)
- Florida
- Cudjoe Key
- 0.64 mi to center
1200 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $841/Night
For 7 Nights CA $5,884
9.1
Exceptional
(474 Reviews)
- Florida
- Sugarloaf Key
- 1.81 mi to center
398.26 ft²
18 Guests
33 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Pet Friendly
CA $627/Night
For 7 Nights CA $4,386
9.8
Exceptional
(551 Reviews)
- Florida
- Sugarloaf Key
- 2.09 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Balcony/Terrace
CA $380/Night
For 7 Nights CA $2,662
10.0
Exceptional
(176 Reviews)
- Florida
- Cudjoe Key
- 0.60 mi to center
1200 ft²
6 Guests
1 Bedroom
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
CA $719/Night
For 7 Nights CA $5,032
9.0
Exceptional
(1 Review)
- Florida
- Cudjoe Key
- 0.61 mi to center
1194.79 ft²
30 Guests
10 Bedrooms
15 Bathrooms
Ocean View
House
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $798/Night
For 7 Nights CA $5,587
10.0
Exceptional
(158 Reviews)
- Florida
- Cudjoe Key
- 0.60 mi to center
1200 ft²
6 Guests
2 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
CA $828/Night
For 7 Nights CA $5,797
8.0
Excellent
(1 Review)
- Florida
- Sugarloaf Key
- 1.11 mi to center
4004.17 ft²
8 Guests
1 Bedroom
4 Bathrooms
Free Cancellation
House
- Private Beach
- Oceanfront
- Fireplace/Heating
CA $3,836/Night
For 7 Nights CA $26,853
10.0
Exceptional
(15 Reviews)
- Cudjoe Key
- Cudjoe Gardens
- 0.24 mi to center
1300 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Balcony/Terrace
- View
CA $267/Night
For 7 Nights CA $1,873
10.0
Exceptional
(12 Reviews)
- Cudjoe Key
- Cutthroat Harbor Estates
- 0.25 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $609/Night
For 7 Nights CA $4,260
10.0
Exceptional
(2 Reviews)
- Florida
- Cudjoe Key
- 0.52 mi to center
1200 ft²
6 Guests
2 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
CA $724/Night
For 7 Nights CA $5,069
10.0
Exceptional
(2 Reviews)
- Sugarloaf Key
- Sugarloaf Shores
- 1.07 mi to center
1440 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
CA $444/Night
For 7 Nights CA $3,111
10.0
Exceptional
(1 Review)
- Florida
- Cudjoe Key
- 0.46 mi to center
1200 ft²
6 Guests
2 Bedrooms
4 Bathrooms
Ocean View
House
- Pool
- Ocean View
- Balcony/Terrace
CA $883/Night
For 7 Nights CA $6,181
10.0
Exceptional
(1 Review)
- Sugarloaf Key
- Sugarloaf Shores
- 0.30 mi to center
960 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Parking
CA $380/Night
For 7 Nights CA $2,662
10.0
Exceptional
(1 Review)
- Cudjoe Key
- Cutthroat Harbor Estates
- 0.33 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $305/Night
For 7 Nights CA $2,137
10.0
Exceptional
(1 Review)
- Florida
- Sugarloaf Key
- 1.71 mi to center
6 Guests
1 Bedroom
1 Bathroom
Ocean View
RV Rental
- Oceanfront
- Pool
- Ocean View
CA $162/Night
For 7 Nights CA $1,136
10.0
Exceptional
(1 Review)
- Cudjoe Key
- Cutthroat Harbor Estates
- 0.56 mi to center
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Pool
- Oceanfront
- Pool
CA $147/Night
For 7 Nights CA $1,029
9.8
Exceptional
(196 Reviews)
- Florida
- Cudjoe Key
- 0.64 mi to center
1200 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
CA $736/Night
For 7 Nights CA $5,149
9.8
Exceptional
(138 Reviews)
- Florida
- Cudjoe Key
- 0.59 mi to center
1100 ft²
6 Guests
2 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
CA $548/Night
For 7 Nights CA $3,836
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