Holiday Homes in Sugarloaf Key

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Sugarloaf Key holiday homes

Pool
The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is NZ$3,914
includes taxes & fees
3 Jan - 4 Jan 2026
The Hemingway - Beach Houses Key West
House
Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is NZ$1,351
includes taxes & fees
6 Jan - 7 Jan 2026
Starlight Serenity - Hideaway w Stunning Views
Fridge, microwave, oven, stovetop
Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
The price is NZ$1,197
includes taxes & fees
6 Jan - 7 Jan 2026
Starlight Serenity - Hideaway with Stunning Views
Pool
The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is NZ$3,022
includes taxes & fees
28 Dec - 29 Dec
The Lighthouse - Beach Houses Key West
Pool
Palm - Beach Houses Key West

Palm - Beach Houses Key West

Palm - Beach Houses Key West
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
The price is NZ$3,436
includes taxes & fees
4 Jan - 5 Jan 2026
Palm - Beach Houses Key West
Pool
Hammock House - Beach Houses Key West

Hammock House - Beach Houses Key West

Hammock House - Beach Houses Key West
Sugarloaf Key
8.0 out of 10, Very good, (2)
"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$6,056
includes taxes & fees
3 Jan - 4 Jan 2026
Hammock House - Beach Houses Key West
Outdoor dining
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is NZ$1,045
includes taxes & fees
10 Jan - 11 Jan 2026
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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

SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is NZ$1,045
includes taxes & fees
18 Jan - 19 Jan 2026
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
House
Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is NZ$5,715
includes taxes & fees
20 Jan - 21 Jan 2026
Waterfront Luxury Home - Tidelands House
Outdoor pool
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.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (65)
"Excellent secluded location but near everything Thanks!!!!!"
United States
Gary D.
The price is NZ$2,255
includes taxes & fees
7 Jan - 8 Jan 2026
One of the very few beach houses with a daily, rental license in the Keys.
Pool
The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
The price is NZ$4,559
includes taxes & fees
4 Jan - 5 Jan 2026
The Shellstone House at Solaire Lunara Bay
Pool
Capmar House at Lunara Bay

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is NZ$2,713
includes taxes & fees
5 Jan - 6 Jan 2026
Capmar House at Lunara Bay
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
The price is NZ$1,424
includes taxes & fees
1 Jan - 2 Jan 2026
Old Florida Style, wrap around porch, boat basin for dockage, open water
Fridge, microwave, oven, stovetop
Springtide House at Lunara Bay

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
The price is NZ$2,626
includes taxes & fees
4 Jan - 5 Jan 2026
Springtide House at Lunara Bay
Outdoor dining
Larkshine House at Lunara Bay

Larkshine House at Lunara Bay

Larkshine House at Lunara Bay
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (7)
"well maintained, clean, easy to access"
United States
Raj P.
The price is NZ$4,232
includes taxes & fees
4 Jan - 5 Jan 2026
Larkshine House at Lunara Bay
A heated pool
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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
The price is NZ$1,054
includes taxes & fees
4 Jan - 5 Jan 2026
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Terrace/patio
The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
The price is NZ$2,713
includes taxes & fees
4 Jan - 5 Jan 2026
The Seagate Estate at Lunara Bay
Outdoor pool, a heated pool
Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19)
"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$1,223
includes taxes & fees
4 Jan - 5 Jan 2026
Spanish Queen @Venture Out, Cudjoe Key
House
Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is NZ$3,310
includes taxes & fees
20 Jan - 21 Jan 2026
Capmar House by Brightwild Huge Home Pool
Exterior
Fishermen's Paradise | Pool, dock, gorgeous home

Fishermen's Paradise | Pool, dock, gorgeous home

Fishermen's Paradise | Pool, dock, gorgeous home
Big Pine Key
9.8 out of 10, Exceptional, (23)
"The location was very nice and secluded. The house was perfect for a family of five. The pool was great spent a lot of time in it. Lots to do in the area. The only complaint we had is the master bedroom bed mattress needs to be replaced. It seemed like it was very old possibly even broken communication with Karen was perfect. Everything about the trip was good :) "
United States
Michelle S.
The price is NZ$2,413
includes taxes & fees
21 Jan - 22 Jan 2026
Fishermen's Paradise | Pool, dock, gorgeous home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sugarloaf Key Hotel Reviews

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"We didn't know there was breakfast until this survey! How did we miss it? The pet friendliness was great. Our dog was happy about the grass out front and the availability of ice. She loves ice."
Eric 2-night trip
Posted 1 day ago
Hyatt Centric Key West Resort and Spa

Find out more about Sugarloaf Key

Sugarloaf Key Holiday Homes information

Number of reviews
490
Accommodation
841 Holiday Homes
Lowest Price
NZ$1,045
Highest Price
NZ$6,056

Explore a world of travel with Expedia