A waterfront with a pier, calm water, and houses with palm trees in the background.

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Check availability on Sugarloaf Key Sports Hotels

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Sugarloaf Key adventure hotels

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
A sunset view with a thatched structure and a palm tree by a calm body of water.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

1. Parmer's Resort

Parmer's Resort
Summerland Key
United States
Mireya
£154
includes taxes & fees
1 Nov - 2 Nov
Parmer's Resort
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A resort with a swimming pool, beach area, and marina.
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.
Outdoor dining

2. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
United States
Elena S.
£320
includes taxes & fees
8 Oct - 9 Oct
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Pool
Outdoor dining
Sports court
Beach

3. 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
United States
Cheryl V.
£343
includes taxes & fees
8 Oct - 9 Oct
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A waterfront property with a covered porch, a boat dock, and a clear sky.
A marina with boats, a dock, and a white building with a balcony.
A spacious living area with a ceiling fan, a television, and a seating area with a sofa and chairs.
A bedroom with a bed, a ceiling fan, a window with blinds, and a door with a sign.

4. SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
United States
Mckayla S.
£333
includes taxes & fees
13 Oct - 14 Oct
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

5. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
£145
includes taxes & fees
26 Oct - 27 Oct
The Perry Hotel & Marina Key West
Pool
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.
Beach
A covered outdoor area with wicker furniture and string lights.

6. 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
United States
jim b.
£356
includes taxes & fees
14 Oct - 15 Oct
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.
An outdoor patio with a table and chairs, a pergola with hanging lights, and a white fence.
A modern kitchen with built-in appliances, a dining area with a wooden table and chairs, and a cozy bedroom with a bed and a view of the outdoors.
A laundry room with a washer and dryer, a door leading to an outdoor patio with a table and chairs.

7. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
United States
John B.
£379
includes taxes & fees
12 Oct - 13 Oct
Kelly's Kabin - Adorable Private Summerland Key Cottage
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A coastal residential area with houses, a marina, and a flag.
A resort with a swimming pool, beach area, and marina.
A marina with boats docked, a clear sky, and a calm waterway.

8. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
United States
Tammy G.
£389
includes taxes & fees
13 Oct - 14 Oct
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A coastal residential area with houses, RVs, and a clear view of the ocean.
A coastal residential area with houses, a marina, and a flag.
A beachside area with palm trees, picnic tables, and a view of the sea.

9. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
£414
includes taxes & fees
8 Oct - 9 Oct
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Outdoor dining
A resort with a swimming pool, beach area, and marina.
A marina with RVs and mobile homes, a swimming pool, and a view of the ocean.

10. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
United States
Nora Kay F.
£367
includes taxes & fees
8 Oct - 9 Oct
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
View all properties

Top Sugarloaf Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"I did hear roosters, but that's part of the charm of Key West. There was occasional chicken poop on the floors outside, so that's why I gave a 4 for cleanliness, but they do seem to clean it up fairly quickly. Overall I loved the stay. I will go again."
Kevin 2-night trip
Posted 17 hours ago
Casa Marina Key West, Curio Collection by Hilton
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10/10 Excellent
"Great place! Rooms were nice. So was staff. Great breakfast with lots of choices."
Walter 3-night trip
Posted 21 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Great hotel and pool!"
Eli 2-night trip
Posted 22 hours ago
Hilton Garden Inn Key West / The Keys Collection
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"Staff at reception are genuinely welcoming."
Nche 1-night trip
Posted 23 hours ago
Hilton Key West Resort & Marina
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Perfect! Great surroundings, staff & people! Convenient to get to everything!"
Diahann 5-night trip
Posted 1 day ago
Southernmost Beach Resort and Guesthouses
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Great place definitely staying there next time"
Francisca 4-night trip
Posted 2 days ago
Parrot Key Hotel & Villas

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