Sugarloaf Key Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Sugarloaf Key holiday rentals

2 bedrooms, Internet

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is HK$3,989
HK$7,098 total
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway w Stunning Views
Pool

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is HK$6,233
HK$12,088 total
includes taxes & fees
17 Feb - 18 Feb
The Hemingway - Beach Houses Key West
Pool

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is HK$6,835
HK$12,621 total
includes taxes & fees
18 Feb - 19 Feb
The Lighthouse - Beach Houses Key West
Pool

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is HK$4,256
HK$8,945 total
includes taxes & fees
20 Feb - 21 Feb
Private and Exclusive Florida Keys Getaway
Pool

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (10 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
Private and Exclusive Beach Getaway
Pool

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
8.0 out of 10, Very good, (2 reviews)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
The price is HK$12,591
HK$20,843 total
includes taxes & fees
23 Feb - 24 Feb
Private and Exclusive Beach Getaway
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (176 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is HK$1,640
HK$3,156 total
includes taxes & fees
1 Mar - 2 Mar
Aqua Lodges at Hurricane Hole Marina
Living area

Sunshine Key RV Resort & Marina

Sunshine Key RV Resort & Marina
2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (160 reviews)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
Sunshine Key RV Resort & Marina
Marina

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (43 reviews)
"Everything was excellent, awesome host, beautiful vacation!"
United States
Jodi M.
The price is HK$3,283
HK$4,162 total
includes taxes & fees
25 Feb - 26 Feb
Living the Dream Key West Style
Living area

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (299 reviews)
"Great stay in Bug Pine Key! Clean and spacious room, excellent staff and Beautiful views!"
United States
Peter
Old Wooden Bridge Resort and Marina
Exterior

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is HK$3,912
HK$5,109 total
includes taxes & fees
11 Feb - 12 Feb
Resort View 1BR Suite With Direct Pool Access
Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is HK$5,098
HK$8,812 total
includes taxes & fees
10 Mar - 11 Mar
Atlantic View Luxury Villa with Pool
Pool

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
8.8 out of 10, Excellent, (55 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is HK$1,934
HK$3,561 total
includes taxes & fees
23 Feb - 24 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor dining

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (163 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
The price is HK$1,934
HK$3,406 total
includes taxes & fees
12 Feb - 13 Feb
Cottage with Pool and Dockage, just minutes to Key West
Exterior

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Great location. "
United States
Davian k.
The price is HK$1,555
HK$3,871 total
includes taxes & fees
25 Feb - 26 Feb
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Interior

Relax by Florida Keys Beaches, just a 7-min drive away

Relax by Florida Keys Beaches, just a 7-min drive away
Cudjoe Key
9.8 out of 10, Exceptional, (201 reviews)
"The cottage was clean and the location was nice and quiet. "
United States
Jaconica B.
The price is HK$1,876
HK$4,824 total
includes taxes & fees
27 Feb - 28 Feb
Relax by Florida Keys Beaches, just a 7-min drive away
Exterior

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is HK$3,039
HK$5,782 total
includes taxes & fees
13 Mar - 14 Mar
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
A heated pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (143 reviews)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is HK$3,898
HK$7,715 total
includes taxes & fees
2 Mar - 3 Mar
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Terrace/patio

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (178 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is HK$1,953
HK$3,783 total
includes taxes & fees
23 Feb - 24 Feb
Waterfront Home
Terrace/patio

Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location - quiet and secluded - away from everything but not so far away that you felt isolated. All very clean and amenities were as described."
United Kingdom
Robert
The price is HK$2,516
HK$3,552 total
includes taxes & fees
23 Feb - 24 Feb
Star Room Barnacle Resort
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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Top Sugarloaf Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Great location !! Beach was wonderful. Beautiful place. Definitely will be back. "
Danny 2-night trip
Posted 20 hours ago
Casa Marina Key West, Curio Collection by Hilton

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