Holiday Homes in Sugarloaf Key

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Sugarloaf Key and around

Our top choices for Sugarloaf Key holiday homes

🌴 TROPICAL RETREAT 🌴 RV in the Keys

10.0 out of 10, Exceptional, (1)
"Its clean and plenty of room.Outdoor seating is wonderful. Could use a gas grill. But definitely a great place."
The price is €288
includes taxes & fees
2 Sept - 3 Sept
🌴 TROPICAL RETREAT 🌴 RV in the Keys

The Lighthouse - Beach Houses Key West

9.6 out of 10, Exceptional, (11)
"We saved up for 3 years for this trip and this property did not disappoint! Thank you for sharing your beautiful piece of paradise with us!"
The Lighthouse - Beach Houses Key West

The Hemingway - Beach Houses Key West

9.8 out of 10, Exceptional, (7)
"Perfect location way off the path if you like seclusion."
The Hemingway - Beach Houses Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West

The price is €488
includes taxes & fees
2 Sept - 3 Sept
Charming 3-bedroom house in Big Pine Key near Beach and Key West

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (98)
"This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. "
The price is €618
includes taxes & fees
1 Oct - 2 Oct
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (81)
"The house was clean as a whistle, has tons of storage, came with everything you need, and is well located. Our husbands really loved the boat launch and docking, the pool and amenities are well kept, security in the park was well done, and the owner are very pleasant and responsive."
The price is €417
includes taxes & fees
2 Sept - 3 Sept
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Keys 3 Bedroom Corner Home near Beach & Key West

9.4 out of 10, Exceptional, (9)
"Great location, right in the middle keys, easy access to everything. "
The price is €544
includes taxes & fees
2 Sept - 3 Sept
Keys 3 Bedroom Corner Home near Beach & Key West

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is €522
includes taxes & fees
2 Sept - 3 Sept
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Floralee House in Key West

2.0 star property
The price is €2,193
includes taxes & fees
3 Sept - 4 Sept
Floralee House in Key West

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (119)
"We enjoyed our stay in Kelly's Kabin. The house was very clean and comfortable, and was in a great location for exploring the mid to lower Keys. "
The price is €434
includes taxes & fees
2 Sept - 3 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage

Waterfront Luxury Home - Tidelands House

2.0 star property
The price is €2,854
includes taxes & fees
3 Sept - 4 Sept
Waterfront Luxury Home - Tidelands House

New Crestwood House by Brightwild Huge Pool

2.0 star property
The price is €2,720
includes taxes & fees
21 Sept - 22 Sept
New Crestwood House by Brightwild Huge Pool

Brand New Build Larkshine House - Pool

2.0 star property
The price is €2,802
includes taxes & fees
3 Sept - 4 Sept
Brand New Build Larkshine House - Pool

Palmgale House in Key West

2.0 star property
The price is €2,193
includes taxes & fees
30 Sept - 1 Oct
Palmgale House in Key West

Brand New Catchlight House With Private Pool

2.5 star property
The price is €2,193
includes taxes & fees
3 Sept - 4 Sept
Brand New Catchlight House With Private Pool

Mirador House by Brightwild Pool Dock

2.0 star property
The price is €2,058
includes taxes & fees
3 Sept - 4 Sept
Mirador House by Brightwild Pool Dock

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (237)
"Clean and inviting property, great location, attentive host. Highly recommend."
The price is €718
includes taxes & fees
2 Sept - 3 Sept
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Suncoast House by Brightwild Pool Boat Dock

2.0 star property
The price is €2,058
includes taxes & fees
3 Sept - 4 Sept
Suncoast House by Brightwild Pool Boat Dock

Springtide House by Brightwild Waterfront Pool

2.0 star property
The price is €1,653
includes taxes & fees
2 Sept - 3 Sept
Springtide House by Brightwild Waterfront Pool

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (7)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is €545
includes taxes & fees
2 Sept - 3 Sept
Island Time #110 Ocean Views - Cudjoe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Find out more about Sugarloaf Key

Sugarloaf Key Holiday Homes information

Number of reviews
Accommodation
852 Holiday Homes
Lowest Price
€309
Highest Price
€918

Explore a world of travel with Expedia

Explore a world of travel with Expedia