Lower Sugarloaf Key Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Lower Sugarloaf Key holiday rentals

Living area

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (336 reviews)
"I love the place, for the next time I will stay for more days "
United States
Kenia
The price is HK$909
HK$2,124 total
includes taxes & fees
31 May - 1 Jun
Old Wooden Bridge Resort and Marina
Pool

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (62 reviews)
"The location was very good and the host was responsive. "
United States
Lilly A.
The price is HK$1,586
HK$3,126 total
includes taxes & fees
20 May - 21 May
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Interior

🌴 TROPICAL RETREAT 🌴 RV in the Keys

🌴 TROPICAL RETREAT 🌴 RV in the Keys
Big Pine Key
9.4 out of 10, Exceptional, (6 reviews)
"Had a great time. The owner was very communicative through the whole process. Camper had everything thing we could have needed. We really enjoyed our stay and if we ever decide to go to the keys again, we will definitely book with Heather and her camper. "
United States
Lorie W.
The price is HK$1,167
HK$2,688 total
includes taxes & fees
2 Jun - 3 Jun
🌴 TROPICAL RETREAT 🌴 RV in the Keys
Outdoor dining

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (99 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveller
The price is HK$1,586
HK$3,334 total
includes taxes & fees
18 May - 19 May
Canal front, dockage, 2 bedroom, 2 bath
Property grounds

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (14 reviews)
"Host was great!!! Unit very clean well stocked with beautiful view."
United States
Lisa F.
The price is HK$1,762
HK$3,711 total
includes taxes & fees
2 Jun - 3 Jun
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Exterior

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

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (88 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is HK$1,950
HK$4,381 total
includes taxes & fees
18 May - 19 May
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Exterior

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (2 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is HK$4,405
HK$8,039 total
includes taxes & fees
27 May - 28 May
Atlantic View Luxury Villa with Pool
A heated pool

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is HK$1,562
HK$4,702 total
includes taxes & fees
17 May - 18 May
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is HK$1,684
HK$4,147 total
includes taxes & fees
10 Jun - 11 Jun
Kelly's Kabin - Adorable Private Summerland Key Cottage
Outdoor pool, a heated pool

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (25 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is HK$2,741
HK$5,329 total
includes taxes & fees
18 May - 19 May
Spanish Queen @Venture Out, Cudjoe Key
Beach

Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (105 reviews)
"Wonderful family getaway"
United States
Anthony V.
Old Florida Style, wrap around porch, boat basin for dockage, open water
Marina

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (168 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is HK$2,741
HK$5,448 total
includes taxes & fees
3 Jun - 4 Jun
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Pool

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 HK$4,522
HK$9,287 total
includes taxes & fees
27 May - 28 May
Private and Exclusive Florida Keys Getaway
Property grounds

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, (156 reviews)
"Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. "
United States
Peggy H.
The price is HK$2,545
HK$5,212 total
includes taxes & fees
2 Jun - 3 Jun
Cudjoe Cottages, swimming pool, just 20 miles from Key West
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.
Summerland Key
8.8 out of 10, Excellent, (68 reviews)
"Such a beautiful home, the view is to die for. It could definitely use some upgrades like the washer and dryer, but can’t beat the location and the fact that its beachfront. "
United States
LIZ
The price is HK$4,691
HK$11,146 total
includes taxes & fees
17 May - 18 May
One of the very few beach houses with a daily, rental license in the Keys.
Front of property

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (186 reviews)
"Beautiful location, quick reply when you contact them. The bar and restaurant were so nice!! We would definitely stay again. "
United States
Stacy
The price is HK$915
HK$2,342 total
includes taxes & fees
18 May - 19 May
Aqua Lodges at Hurricane Hole Marina
Outdoor pool

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (37 reviews)
"The location was fabulous, due to the hotel’s amenities. Ie the hourly transport to downtown.pools and restaurants. The accommodations were a bit dated but adequate. The host responded immediately to our request! "
United States
Leigh P.
The price is HK$1,958
HK$3,955 total
includes taxes & fees
19 May - 20 May
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Terrace/patio

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (14 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
The price is HK$2,741
HK$6,764 total
includes taxes & fees
18 May - 19 May
House of the Rising Sun - VO479
Pool

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is HK$3,359
HK$6,012 total
includes taxes & fees
15 Jun - 16 Jun
Paradise found
Terrace/patio

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (8 reviews)
"Gorgeous place! Had an excellent time. Very clean and easy check-in/out process. Highly recommend!"
United States
Susan B.
The price is HK$3,494
HK$7,181 total
includes taxes & fees
1 Jun - 2 Jun
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
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 Lower Sugarloaf Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"The best location in Key West to have the best of the both worlds: rest and recharge at the beach, and walking distance to duval street where all the main attractions are. The staff at the hotel is one of the best I have encountered. And the private beach is truly a hidden beauty!"
Maikel 2-night trip
Posted 2 hours ago
Casa Marina Key West, Curio Collection by Hilton

Find out more about Lower Sugarloaf Key

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