COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Sugarloaf Rentals

Updating...

age 0-16
228 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

228 Houses

Florida Keys at it's best

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$171

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$233

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$175

South Point Shores

Sugarloaf house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$177

Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe

Sugarloaf house

5 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$330

PARADISE POINT - Amazing Views, Luxurious Open Water Home W/ Pool, Tiki, Dockage

Sugarloaf house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 32 minutes

Price per night from

$457

Great rentals within 20 miles that match your search

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

Price per night from

$477

Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.

Key West house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$256

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$569

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$245

Starfish House - Dock your boat at your front door

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$521

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$427

Truman Annex-Steps to Famous Duval Street

Key West townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$391

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$552

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 48 minutes

Price per night from

$228

Catch of the Day!

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$125

Hogfish Retreat

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$177

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$143

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$445

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$473

Buccaneer Boathouse

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$127

Price per night from

$154

Private, heated pool. Private yard.

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$171

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$330

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 42 minutes

Price per night from

$569

Coconut Cay

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$182

Hawkins Heaven

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$148

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$217

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 29 minutes

Price per night from

$251

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$294

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$256

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$171

Tranquility in Paradise - Cudjoe

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$217

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$382

OLD TOWN, 2 Bedrm, Pool, Fully Equipped Kitchen, Wrap around private porch, W/D

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$171

Water's Edge

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$150

Latitude Adjustment

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$157

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$222

Viewing 38 of 228
rentals in Sugarloaf

×

Also consider