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Our top choices for Sugarloaf Key vacation homes

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Perfect location way off the path if you like seclusion."
United States
Jonathan L.
The price is AED 2,929
AED 5,681 total
includes taxes & fees
17 Feb - 18 Feb
The Hemingway - Beach Houses Key West

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
8.0 out of 10, Very Good, (2 reviews)
"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 5,919
AED 10,070 total
includes taxes & fees
23 Feb - 24 Feb
Private and Exclusive Beach Getaway

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is AED 2,000
AED 4,167 total
includes taxes & fees
20 Feb - 21 Feb
Private and Exclusive Florida Keys Getaway

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is AED 3,212
AED 5,961 total
includes taxes & fees
8 Feb - 9 Feb
The Lighthouse - Beach Houses Key West

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (102 reviews)
"Great location. "
United States
Davian k.
The price is AED 621
AED 1,655 total
includes taxes & fees
8 Feb - 9 Feb
SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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
Cudjoe Key
The price is AED 920
AED 2,471 total
includes taxes & fees
3 Mar - 4 Mar
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is AED 1,010
AED 2,230 total
includes taxes & fees
1 Mar - 2 Mar
Kelly's Kabin - Adorable Private Summerland Key Cottage

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is AED 733
AED 2,224 total
includes taxes & fees
9 Feb - 10 Feb
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is AED 10,032
AED 14,856 total
includes taxes & fees
16 Feb - 17 Feb
The Fairhaven House at Solaire Lunara Bay

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
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Very clean! Good location. "
United States
January M.
The price is AED 1,253
AED 2,887 total
includes taxes & fees
25 Feb - 26 Feb
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.6 out of 10, Good, (13 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is AED 909
AED 1,893 total
includes taxes & fees
11 Feb - 12 Feb
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Relax by Florida Keys Beaches, just a 7-min drive away

Relax by Florida Keys Beaches, just a 7-min drive away
Cudjoe Key
9.8 out of 10, Exceptional, (201 reviews)
"Will definitely stay here again "
United States
Jeannine R.
The price is AED 1,010
AED 2,430 total
includes taxes & fees
27 Feb - 28 Feb
Relax by Florida Keys Beaches, just a 7-min drive away

The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home with great outdoor space and we loved the pool and private dock"
United States
Sharon L.
The price is AED 5,858
AED 11,149 total
includes taxes & fees
16 Feb - 17 Feb
The Shellstone House at Solaire Lunara Bay

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
Sands
8.8 out of 10, Excellent, (3 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is AED 1,355
AED 2,892 total
includes taxes & fees
1 Mar - 2 Mar
Charming 3-bedroom house in Big Pine Key near Beach and Key West

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is AED 1,429
AED 2,689 total
includes taxes & fees
5 Mar - 6 Mar
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is AED 1,253
AED 2,846 total
includes taxes & fees
6 Mar - 7 Mar
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is AED 1,377
AED 2,677 total
includes taxes & fees
6 Feb - 7 Feb
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is AED 1,286
AED 2,481 total
includes taxes & fees
16 Feb - 17 Feb
Spanish Queen @Venture Out, Cudjoe Key

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is AED 9,043
AED 13,744 total
includes taxes & fees
16 Feb - 17 Feb
Waterfront Luxury Home - Tidelands House

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (12 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AED 1,250
AED 2,849 total
includes taxes & fees
21 Feb - 22 Feb
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.
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Top Sugarloaf Key Hotel Reviews