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
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 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 dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.
A sunset view with a thatched structure and a palm tree by a calm body of water.
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
£132
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.
Outdoor dining
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.

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
9 Oct - 10 Oct
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Pool
Outdoor dining
Sports court
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

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 bedroom with a bed, a ceiling fan, a window with blinds, and a door with a sign.
A spacious living area with a ceiling fan, a television, and a seating area with a sofa and chairs.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
United States
Mckayla S.
£343
includes taxes & fees
15 Oct - 16 Oct
SAVE BIG $$$ 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 balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.
A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

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
Beach
Sports court
A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.

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.
£367
includes taxes & fees
23 Oct - 24 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.
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.
An outdoor patio with a table and chairs, a pergola with hanging lights, and a white fence.

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

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
United States
John B.
£380
includes taxes & fees
11 Oct - 12 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.
Outdoor dining
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, a marina, and a flag.
A coastal residential area with houses, RVs, and a clear view of the ocean.
A resort with a swimming pool, beach area, and marina.

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
£416
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.
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.
A coastal residential area with houses, a marina, and a flag.

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
9 Oct - 10 Oct
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
View all properties

Top Sugarloaf Key Hotel Reviews

Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Very nice and staff was great."
Andre 4-night trip
Posted less than an hour ago
Ibis Bay Beach Resort
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 3 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 4 hours ago
Hilton Key West Resort & Marina
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Location is great. Room was very clean. Beds were great and the rain shower was amazing."
Michael 2-night trip
Posted 6 hours ago
Pier House Resort & Spa
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 7 hours 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 1 day ago
Parrot Key Hotel & Villas
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Clear room, great views"
Mary 6-night trip
Posted 3 days ago
Casa Marina Key West, Curio Collection by Hilton

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