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

Find Family Hotels in Sugarloaf Key, FL from CA $162

  • 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 Family Hotels

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Sugarloaf Key family-friendly hotels

A waterfront building with a flat roof, large windows, and a balcony.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
CA $170
CA $191 total
includes taxes & fees
Oct 8 - Oct 9
Sugar Loaf Lodge
A wooden deck with a hanging hammock and a view of a green landscape.
Water Views
A modern kitchen with a central island, bar stools, and a dining area with a round table.
A spacious living area with a kitchen island, a staircase, and large windows offering a view of the outdoors.

2. Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
CA $306
CA $885 total
includes taxes & fees
Oct 14 - Oct 15
Starlight Serenity - Hideaway with Stunning Views
A wooden deck with a railing, wicker chairs, and a view of greenery.
A modern kitchen with a large island, white cabinetry, and three wicker bar stools.
A modern bathroom with a glass-enclosed shower, a toilet, and a small window.
A two-story house with a balcony and a staircase leading to the upper level.

3. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
Summerland Key
CA $398
CA $968 total
includes taxes & fees
Oct 13 - Oct 14
Starlight Serenity - Hideaway w Stunning Views
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
A hotel room with a bed, a flat-screen TV, a small kitchenette, and a balcony with a view of palm trees and the ocean.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

4. Parmer's Resort

Parmer's Resort
Summerland Key
CA $180
CA $250 total
includes taxes & fees
Nov 2 - Nov 3
Parmer's Resort
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

5. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
CA $144
CA $162 total
includes taxes & fees
Oct 14 - Oct 15
Looe Key Reef Resort
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
A balcony with a view of neighboring houses, a street, and a clear sky.
A waterfront property with a two-story building, a covered outdoor area, and a dock.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
CA $198
CA $604 total
includes taxes & fees
Oct 9 - Oct 10
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
A clear view of turquoise ocean water and a blue sky with clouds.
A hotel room with a large bed, a view of the ocean, a balcony with a chair, and a painting of coconuts.
A waterfront hotel with a pool, palm trees, and a wooden dock.

7. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
  • Splash into family fun with 6 outdoor pools, free bike rentals, and poolside adventures at this waterfront Key West resort.
CA $168
CA $273 total
includes taxes & fees
Oct 12 - Oct 13
Hilton Key West Resort & Marina
A detailed mural of a pirate ship on a tiled pathway surrounded by palm trees and benches.
A modern living room with a sectional sofa, a small round table, and a potted plant.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

8. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
  • Family fun by the pool awaits with cabanas and activities, just minutes from Smathers Beach for adventure-filled stays.
CA $157
CA $217 total
includes taxes & fees
Oct 8 - Oct 9
Hilton Garden Inn Key West / The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A hotel room with a balcony, a bed, a desk, and two chairs.
A balcony with wicker furniture and a view of the ocean and palm trees.
Breakfast area

9. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
CA $241
CA $271 total
includes taxes & fees
Oct 7 - Oct 8
Hampton Inn Key West FL
A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.
A modern office space with a reception desk, computer, and seating area.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
  • Family-friendly Key West getaway with outdoor pool, beach access, and daily breakfast to fuel sun-soaked adventures.
CA $178
CA $241 total
includes taxes & fees
Oct 15 - Oct 16
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
View all properties

Choose what matters most at family-friendly hotels in Sugarloaf Key

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Sugarloaf Key Hotel Reviews

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Great place definitely staying there next time"
Francisca 4-night trip
Posted 12 hours ago
Parrot Key Hotel & Villas
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Hot water in showers, bed comfort was okay, food was decent at the bars/restaurants, staff was friendly, pool clean and open until 11pm. Lots of fun games to play outside. The property and rooms were clean and the shuttle service to town was easy and very helpful!"
Michelle 5-night trip
Posted 16 hours ago
Blue Flamingo Resort Key West
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Love pier house resort"
William 3-night trip
Posted 21 hours ago
Pier House Resort & Spa
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"This place was great quiet and close to everything"
Jason Victor 3-night trip
Posted 2 days ago
The Southernmost Inn - Adults Only
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
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"This was our second time to stay here and this place never disappoints. Staff is wonderful too"
Jonathan 4-night trip
Posted 3 days ago
Hilton Key West Resort & Marina

Explore a world of travel with Expedia