Search Vacation Homes in Sugarloaf Key

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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Vacation Homes in Sugarloaf Key

Beach nearby
Beach Getaway in the Florida Keys
Beach Getaway in the Florida Keys
8.4 out of 10, Very Good, (7)
"Amazing property and views. Tom was great and very helpful with places to go and things to do. Will definitely recommend!!"
United States
Robyn M.
The price is AED 3,212
AED 7,122 total
includes taxes & fees
5 Nov - 6 Nov
Beach Getaway in the Florida Keys
Pool
Palm - Beach Houses Key West
Palm - Beach Houses Key West
10.0 out of 10, Exceptional, (14)
"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"
United States
Crystal G.
The price is AED 2,323
AED 5,017 total
includes taxes & fees
4 Nov - 5 Nov
Palm - Beach Houses Key West
Pool
Hammock House - Beach Houses Key West
Hammock House - Beach Houses Key West
8.0 out of 10, Very Good, (2)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
The price is AED 8,060
AED 12,809 total
includes taxes & fees
3 Nov - 4 Nov
Hammock House - Beach Houses Key West
Terrace/patio
Cozy Cottage in Big Pine Key – 35 Min to Key West, Pool & Free Parking
Cozy Cottage in Big Pine Key – 35 Min to Key West, Pool & Free Parking
9.0 out of 10, Wonderful, (9)
"Lovely unit, clean and accessible. Would recommend."
United States
Shannon C.
The price is AED 533
AED 1,137 total
includes taxes & fees
30 Oct - 31 Oct
Cozy Cottage in Big Pine Key – 35 Min to Key West, Pool & Free Parking
Smart TV
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Charming 3-bedroom house in Big Pine Key near Beach and Key West
The price is AED 716
AED 2,160 total
includes taxes & fees
26 Oct - 27 Oct
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Smart TV, books
Keys 3 Bedroom Corner Home near Beach & Key West
Keys 3 Bedroom Corner Home near Beach & Key West
9.4 out of 10, Exceptional, (10)
"Enjoyed our stay"
United States
Patricia H.
The price is AED 1,429
AED 3,076 total
includes taxes & fees
8 Nov - 9 Nov
Keys 3 Bedroom Corner Home near Beach & Key West
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.6 out of 10, Exceptional, (84)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
United States
drywall c.
The price is AED 1,102
AED 2,563 total
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water
Outdoor pool, a heated pool
OCT. & NOV. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
OCT. & NOV. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
9.8 out of 10, Exceptional, (81)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is AED 584
AED 1,643 total
includes taxes & fees
26 Oct - 27 Oct
OCT. & NOV. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Outdoor dining
OCT. & NOV. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
OCT. & NOV. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
9.6 out of 10, Exceptional, (98)
"Clean place with room for 2 couples. Everything you need."
United States
Jason W.
The price is AED 511
AED 1,553 total
includes taxes & fees
29 Oct - 30 Oct
OCT. & NOV. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Fridge, microwave, oven, stovetop
Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key Cottage
9.8 out of 10, Exceptional, (119)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is AED 744
AED 1,886 total
includes taxes & fees
26 Oct - 27 Oct
Kelly's Kabin - Adorable Private Summerland Key Cottage
A heated pool
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2.5 star property
9.2 out of 10, Wonderful, (7)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is AED 694
AED 2,169 total
includes taxes & fees
26 Oct - 27 Oct
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
A heated pool
Island Time #110 Ocean Views - Cudjoe Key
Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
9.4 out of 10, Exceptional, (10)
"Greta property, really enjoyed the water view and the bbq grill "
United States
William B.
The price is AED 771
AED 2,278 total
includes taxes & fees
27 Oct - 28 Oct
Island Time #110 Ocean Views - Cudjoe Key
Outdoor pool
One of the very few beach houses with a daily, rental license in the Keys.
One of the very few beach houses with a daily, rental license in the Keys.
8.8 out of 10, Excellent, (64)
"My family and I had an incredible stay. We utilized every available component of the home including the dock. Property manager provided us with 2 available free ramps to drop off our jet-skis. We settled on the ramp located on Blimp Road, which was a 10 minute drive and 15-20 minute ride on the skis. We were able to tie off our skis our whole stay with no issues. Home was exactly as disclosed and worked great for our family. Communication was great, with quick respond time. "
United States
Yissel W.
The price is AED 1,980
AED 4,833 total
includes taxes & fees
26 Oct - 27 Oct
One of the very few beach houses with a daily, rental license in the Keys.
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, (117)
"Deer in the front yard, perfect location, clean and friendly "
United States
Sara H.
The price is AED 826
AED 1,980 total
includes taxes & fees
28 Oct - 29 Oct
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
On the beach, beach towels
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (238)
"Lovely property. Well equipped, nicely decorated, perfect for our stay."
United States
Karen M.
The price is AED 1,286
AED 2,977 total
includes taxes & fees
26 Oct - 27 Oct
Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes
A heated pool
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
2.0 star property
9.0 out of 10, Wonderful, (7)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
United States
Rebecca G.
The price is AED 868
AED 2,387 total
includes taxes & fees
26 Oct - 27 Oct
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Outdoor pool, a heated pool
Spanish Queen @Venture Out, Cudjoe Key
Spanish Queen @Venture Out, Cudjoe Key
9.4 out of 10, Exceptional, (19)
"We enjoyed our stay at venture out at the Spanish main residence it was lovely and we are going to return again next year"
United States
susan l.
The price is AED 1,286
AED 2,511 total
includes taxes & fees
27 Oct - 28 Oct
Spanish Queen @Venture Out, Cudjoe Key
A heated pool
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
2.0 star property
The price is AED 675
AED 2,148 total
includes taxes & fees
26 Oct - 27 Oct
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A heated pool
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
2.0 star property
The price is AED 771
AED 2,267 total
includes taxes & fees
26 Oct - 27 Oct
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Property grounds
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
2.0 star property
The price is AED 964
AED 2,510 total
includes taxes & fees
8 Nov - 9 Nov
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on 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.
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Top Sugarloaf Key Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Really enjoyed our stay here. Rooms were clean and beds were super comfy.. the staff were all so nice! The bartenders at the pool bar made excellent STRONG drinks! Love the shuttle to and from downtown, really came in handy!!! "
stephanie 3-night trip
Posted 1 day ago
DoubleTree Resort by Hilton Grand Key - Key West