Holiday Homes in Sugarloaf Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Sugarloaf Key holiday homes

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is NZ$1,187
includes taxes & fees
28 May - 29 May
Starlight Serenity - Hideaway with Stunning Views

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 NZ$2,011
includes taxes & fees
26 May - 27 May
Private and Exclusive Florida Keys Getaway

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is NZ$1,443
includes taxes & fees
28 May - 29 May
Starlight Serenity - Hideaway w Stunning Views

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 NZ$2,455
includes taxes & fees
28 May - 29 May
The Lighthouse - Beach Houses Key West

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (11 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
The price is NZ$3,451
includes taxes & fees
1 June - 2 June
Private and Exclusive Beach Getaway

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
United States
Brian K.
The price is NZ$2,858
includes taxes & fees
18 June - 19 June
The Hemingway - Beach Houses Key West

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 NZ$4,593
includes taxes & fees
9 June - 10 June
Private and Exclusive Beach Getaway

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is NZ$1,054
includes taxes & fees
26 May - 27 May
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (89 reviews)
"Had a great time will be back!! "
United States
Rene V.
The price is NZ$898
includes taxes & fees
1 June - 2 June
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is NZ$981
includes taxes & fees
25 May - 26 May
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
The price is NZ$1,084
includes taxes & fees
25 May - 26 May
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.4 out of 10, Very good, (12 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is NZ$1,324
includes taxes & fees
31 May - 1 June
Charming 3-bedroom house in Big Pine Key near Beach and Key West

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

SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
"Had everything we needed. "
United States
Moriah W.
The price is NZ$845
includes taxes & fees
25 May - 26 May
SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (168 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is NZ$1,186
includes taxes & fees
9 June - 10 June
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is NZ$888
includes taxes & fees
10 June - 11 June
Kelly's Kabin - Adorable Private Summerland Key Cottage

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.8 out of 10, Good, (20 reviews)
"Online photos did not match the house. You entered the house through one of the bedrooms. So privacy for those staying in that room did not exist. The extra you pay when checking in for the club amenities was not worth the expense. "
United States
Seth
The price is NZ$764
includes taxes & fees
27 May - 28 May
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (157 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is NZ$1,040
includes taxes & fees
3 June - 4 June
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is NZ$1,306
includes taxes & fees
15 June - 16 June
Paradise found

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Great place! Perfect location"
United States
Troy B.
The price is NZ$1,113
includes taxes & fees
1 June - 2 June
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (13 reviews)
Island Time #110 Ocean Views - Cudjoe Key
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Sugarloaf Key Holiday Homes information

Number of reviews
768
Accommodation
821 Holiday Homes
Lowest Price
NZ$764
Highest Price
NZ$4,593

Explore a world of travel with Expedia