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

Find Romantic Hotels in Sugarloaf Key, FL

  • 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 availability on Sugarloaf Key Romantic Hotels

Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Sugarloaf Key romantic hotels

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.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
United States
Mckayla S.
￥25,098
￥69,967 total
includes taxes & fees
Oct 4 - Oct 5
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A marina with boats docked, a pool area, and a building with a white facade.
A clear view of turquoise ocean water and a blue sky with clouds.
A marina with numerous boats docked, a swimming pool, and palm trees.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.

2. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
United States
Molly
￥19,959
￥31,699 total
includes taxes & fees
Oct 12 - Oct 13
Hilton Key West Resort & Marina
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
A hotel with a central courtyard, palm trees, and a fountain.
An outdoor patio with tables and chairs, umbrellas, and palm trees.
A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

3. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
United States
Nancy
￥19,447
￥27,205 total
includes taxes & fees
Oct 11 - Oct 12
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A bar area with a thatched roof, wooden chairs, and a poolside view.
A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.
A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

4. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
United States
Jaycie
￥26,170
￥29,441 total
includes taxes & fees
Oct 7 - Oct 8
Hampton Inn Key West FL
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 marina with boats docked, a swimming pool, and palm trees.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

5. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
￥18,395
￥30,343 total
includes taxes & fees
Oct 26 - Oct 27
The Perry Hotel & Marina Key West
A balcony with wicker furniture, a view of the sea, and a spiral staircase.
A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A spacious lobby with a marble floor, leather sofas, and large potted plants.
A beach with palm trees, clear blue water, and a pier extending into the sea.

6. Beachside Resort & Residences

Beachside Resort & Residences
Key West
United States
James
￥13,778
￥30,593 total
includes taxes & fees
Oct 4 - Oct 5
Beachside Resort & Residences
Pool
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A couple holding hands in a tropical setting with palm trees and greenery.

7. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
United States
Esteban
￥18,650
￥29,861 total
includes taxes & fees
Oct 4 - Oct 5
Blue Flamingo Resort Key West
A wooden archway leading to a pool area surrounded by lush tropical vegetation.
A tall palm tree with a white building in the background.
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.
A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

8. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
United States
Anthony
￥20,836
￥32,498 total
includes taxes & fees
Oct 12 - Oct 13
Parrot Key Hotel & Villas
A hotel room with a bed, a view of the beach, a hammock, and beach chairs.
A marina with boats docked, a beach resort building, and palm trees.
A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.
A pool area with blue lounge chairs, a hot tub, and a covered seating area.

9. Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
United States
Stephanie
￥20,103
￥27,708 total
includes taxes & fees
Oct 4 - Oct 5
Ibis Bay Beach Resort
A dining table with plates of food, a drink, and a view of a pool and palm trees.
A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.
A beach with a palm tree and two chairs.
A person standing by a window overlooking a beach with palm trees and the ocean.

10. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
United States
TRICIA LYNN
￥32,991
￥47,076 total
includes taxes & fees
Oct 4 - Oct 5
Margaritaville Beach House Key West
View all properties

Top Sugarloaf Key Hotel Reviews

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Wonderful"
James 2-night trip
Posted 6 hours ago
Hampton Inn Key West FL
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Amazing!"
Naomi 2-night trip
Posted 10 hours ago
Southernmost Beach Resort and Guesthouses
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 customer service and very clean!!!"
Teresa Maria 2-night trip
Posted 16 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Pier House Resort & Spa

Pier House Resort & Spa

8/10 Good
"Location is great if you want to be close to the action. But, it is also quite and laid out well for beach bumming. Iguanas and chickens are everywhere!"
Cliff 4-night trip
Posted 18 hours ago
Pier House Resort & Spa
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Great shuttle service"
Eric 1-night trip
Posted 1 day ago
DoubleTree Resort by Hilton Grand Key - Key West
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

8/10 Good
"Valet parking obligatoire ce qui était pour nous plutôt une nuisance qu’un avantage car nous sortions souvent visiter les alentours! Nous ne pouvions pas apporter de boissons alcoolisé au bord de la piscine il fallait les acheter directement au bar de piscine …"
Alexandre 1-night trip
Posted 2 days ago
Parrot Key Hotel & Villas
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"Hotel was great. All of the staff were friendly and accommodating"
Kellie 1-night trip
Posted 2 days ago
The Perry Hotel & Marina Key West

Explore a world of travel with Expedia