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Beach or lakeside relaxation
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267 house rentals

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Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms
3 bathrooms

sleeps 10

Price per night from

$384

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D

Sugarloaf Key house

4 bedrooms
4 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Cassie's Paradise

Sugarloaf Key house

5 bedrooms
4 bathrooms

sleeps 10

Price per night from

$5,707

Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V

Sugarloaf Key house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag

Sugarloaf Key house

4 bedrooms
4 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$1,137

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 30 minutes

Price per night from

$320

Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D

Sugarloaf Key house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di

Sugarloaf Key house

4 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private

Sugarloaf Key house

3 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Price per night from

$179

Great rentals within 20 miles that match your search

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 56 minutes

Price per night from

$515

Southernmost Beauty

Key West house

3 bedrooms
3 bathrooms

sleeps 6

Responds fast! avg. 3 hours 56 minutes

Price per night from

$267

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

Key West house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$165

Salty Retreat

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Price per night from

$447

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$475

Buccaneer Boathouse

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$140

Ambrosia - OLD TOWN/HISTORIC SEAPORT, large POOL, wrap around porch, washer/dry

Key West condo

1 bedroom
1 bathroom

sleeps 2

Price per night from

$155

Florida Keys at it's best

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$241

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

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

Price per night from

$286

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

2 bedrooms
1 bathroom

sleeps 6

Price per night from

$457

Hogfish Retreat

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$178

Conch House - Dock Your Boat

Little Torch Key house

4 bedrooms
4 bathrooms

sleeps 7

Price per night from

$773

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

$572

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

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 7

Price per night from

$307

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$341

Starfish House - Dock your boat at your front door

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$572

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms
3 bathrooms

sleeps 6

Price per night from

$481

Truman Annex-Steps to Famous Duval Street

Key West townhouse

2 bedrooms
2 bathrooms

sleeps 4

Responds fast! avg. 3 hours 56 minutes

Price per night from

$393

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

Summerland Key house

4 bedrooms
2 bathrooms

sleeps 8

Price per night from

$555

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

Price per night from

$1,944

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$910

Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$210

Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$228

SEAPORT PANORAMA at Galleon Resort (Beach-Pool & Hot Tub-BBQ-55” TV-Jacuzzi)

Key West condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$910

One-bedroom time share suite in the heart of Old Key West

Key West condo

1 bedroom
1 bathroom

sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$338

Key West Island Vacation

Key West house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 1 hour 8 minutes

Price per night from

$480

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

Key West house

2 bedrooms
1 bathroom

sleeps 6

Price per night from

$258

Conch Out

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$193

Viewing 38 of 267
rentals in Sugarloaf Key

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Vacation Rentals & House Rentals in Sugarloaf Key

Per night

267 house rentals

Viewing 38 of 267rentals in Sugarloaf Key

Also consider

Viewing 38 of 267
rentals in Sugarloaf Key