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

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Check availability on Sugarloaf Key Shopping Hotels

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Sugarloaf Key hotels with shopping nearby

A wooden deck with a hanging hammock and a view of a green landscape.
Water Views
A spacious living room with a flat-screen TV, a sofa, a dining table, and large windows offering a view of greenery.
A modern kitchen with a central island, bar stools, and a dining area with a round table.

1. Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
United States
Tom H.
Starlight Serenity - Hideaway with Stunning Views
A covered deck with chairs and umbrellas overlooking a beach.
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.
A dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.

2. Parmer's Resort

Parmer's Resort
Summerland Key
United States
Mireya
AED 493
AED 674 total
includes taxes & fees
1 Nov - 2 Nov
Parmer's Resort
A pool area with multiple swimming pools, lounge chairs, and palm trees.
A coastal residential area with houses, a marina, and a flag.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

3. 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.
AED 413
AED 1,462 total
includes taxes & fees
27 Oct - 28 Oct
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.
Outdoor dining
Beach
Pool

4. 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.
AED 521
AED 1,598 total
includes taxes & fees
2 Nov - 3 Nov
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A covered outdoor area with wicker furniture and string lights.
Beach
Pool
Sport court

5. 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.
AED 636
AED 1,743 total
includes taxes & fees
11 Nov - 12 Nov
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A cozy room with a brown leather sofa, a white table, and a ceiling fan.
A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.
A row of houseboats docked at a marina with clear reflections in the water.
A compact kitchen with wooden beams, a dining area with white chairs, and a TV mounted on the wall.

6. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
Punta Brisa
United States
Daisybel
AED 327
AED 885 total
includes taxes & fees
27 Oct - 28 Oct
Old Wooden Bridge Resort and Marina
A pool area with multiple swimming pools, lounge chairs, and palm trees.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Outdoor dining
A marina with boats docked, a clear sky, and a calm waterway.

7. 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
Suzanne T.
AED 659
AED 1,769 total
includes taxes & fees
27 Oct - 28 Oct
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A pool area with multiple swimming pools, lounge chairs, and palm trees.
Outdoor dining
A coastal residential area with houses, a marina, and a flag.
A marina with RVs and mobile homes, a swimming pool, and a view of the ocean.

8. 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.
AED 607
AED 1,707 total
includes taxes & fees
27 Oct - 28 Oct
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
A waterfront property with a covered porch, a boat dock, and a clear sky.
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.
A marina with boats, a dock, and a white building with a balcony.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
United States
Mckayla S.
AED 657
AED 1,722 total
includes taxes & fees
3 Nov - 4 Nov
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A covered outdoor seating area with a view of the ocean and palm trees.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A coastal property with a marina, houses with balconies, and a clear view of the ocean.
Living area

10. Canal-Front Retreat with Dock, Pool & Open Ocean Views

Canal-Front Retreat with Dock, Pool & Open Ocean Views
Cudjoe Key
United States
Catherine C.
AED 659
AED 1,769 total
includes taxes & fees
27 Oct - 28 Oct
Canal-Front Retreat with Dock, Pool & Open Ocean Views
View all properties

Top Sugarloaf Key Hotel Reviews

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"Perfect quiet clean close to everything"
Lori 1-night trip
Posted less than an hour ago
The Southernmost Inn - Adults Only
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

10/10 Excellent
"It was absolutely amazing! Perfect location to everything!!!"
Julie 4-night trip
Posted 1 hour ago
Opal Key Resort & Marina, Key West
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
"Todo muy bueno"
frank 2-night trip
Posted 2 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Gorgeous property in Key West"
Mark 1-night trip
Posted 5 hours ago
Winslow's Bungalows - Key West Historic Inns
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Our stay at the Southern Most was great! The location is perfect and the staff was wonderful. The beach, the pool the rooms were spotless and the staff couldn’t have been any nicer. Highly recommended."
Richard John 3-night trip
Posted 8 hours ago
Southernmost Beach Resort and Guesthouses
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

10/10 Excellent
"It was welled cared for and the staff was very helpful."
Debra K 2-night trip
Posted 16 hours ago
The Reach Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Great hotel and conveniently located in Key West! We truly enjoyed our time there"
Nishantha 1-night trip
Posted 19 hours ago
Casa Marina Key West, Curio Collection by Hilton
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Amazing cute property. Beach lounge, pool, restaurant on site. Close to shopping center."
Jessica 2-night trip
Posted 2 days ago
Ibis Bay Beach Resort

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