Holiday Homes in Sugarloaf Key

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Our top choices for Sugarloaf Key holiday homes

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$1,902
includes taxes & fees
25 Feb - 26 Feb
Private and Exclusive Florida Keys Getaway

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 NZ$2,877
includes taxes & fees
22 Feb - 23 Feb
The Hemingway - Beach Houses Key West

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is NZ$1,405
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is NZ$1,547
includes taxes & fees
12 Mar - 13 Mar
Starlight Serenity - Hideaway w Stunning Views

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.
The price is NZ$3,785
includes taxes & fees
9 Mar - 10 Mar
Private and Exclusive Beach Getaway

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$4,982
includes taxes & fees
13 Mar - 14 Mar
Private and Exclusive Beach Getaway

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
8.8 out of 10, Excellent, (3 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is NZ$1,254
includes taxes & fees
1 Mar - 2 Mar
Charming 3-bedroom house in Big Pine Key near Beach and 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, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is NZ$1,010
includes taxes & fees
1 Mar - 2 Mar
Kelly's Kabin - Adorable Private Summerland Key Cottage

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
The price is NZ$1,114
includes taxes & fees
3 Mar - 4 Mar
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is NZ$1,117
includes taxes & fees
23 Mar - 24 Mar
Spanish Queen @Venture Out, Cudjoe Key

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

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "
United States
Lauren D.
The price is NZ$823
includes taxes & fees
25 Feb - 26 Feb
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (8 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is NZ$994
includes taxes & fees
22 Mar - 23 Mar
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Fun in the Sun in Cudjoe Key! #51

Fun in the Sun in Cudjoe Key! #51
Cudjoe Key
8.6 out of 10, Excellent, (9 reviews)
"This was a beautiful"
United States
Debbie A.
The price is NZ$1,144
includes taxes & fees
9 Mar - 10 Mar
Fun in the Sun in Cudjoe Key! #51

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, (14 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is NZ$859
includes taxes & fees
7 Mar - 8 Mar
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

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

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (83 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is NZ$934
includes taxes & fees
5 Mar - 6 Mar
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON 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, (151 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is NZ$1,208
includes taxes & fees
3 Mar - 4 Mar
Cudjoe Cottages, swimming pool, just 20 miles from Key West

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (66 reviews)
"If you are looking to see spectacular sunrises in the Keys, this location is great. Kitchen is well stocked with everything you need. "
United States
Paula D.
The price is NZ$3,992
includes taxes & fees
14 Mar - 15 Mar
One of the very few beach houses with a daily, rental license in the Keys.

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (12 reviews)
"Great property! Very well maintained and an excellent location. We had a great time! We have stayed here before and definitely will again! Thank You!"
United States
Matthew M.
The price is NZ$1,284
includes taxes & fees
14 Mar - 15 Mar
Island Time #110 Ocean Views - Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is NZ$1,282
includes taxes & fees
6 Mar - 7 Mar
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very good, (123 reviews)
"Great experience "
United States
Peyton S.
The price is NZ$1,087
includes taxes & fees
22 Feb - 23 Feb
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
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

Find out more about Sugarloaf Key

Sugarloaf Key Holiday Homes information

Number of reviews
771
Accommodation
841 Holiday Homes
Lowest Price
NZ$823
Highest Price
NZ$4,982

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