Holiday Rentals in Sugarloaf Key

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Holiday Rentals in Sugarloaf Key

Palm - Beach Houses Key West

Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"Excellent place to stay if you are seeking a getaway off the beaten path. Well landscaped to give privacy to each bungalow. 2 amazing piers to fish/jet ski from. The pool and grill area is a PERFECT place to cool off and escape the heat with the swim up bar. The staff even gave us coconuts to enjoy fresh from their trees. Each day we saw amazing wildlife and even had key deer visit us. We are considering booking the whole place for a family reunion. Would also make for a great corporate...
United States
Robert K.
The price is €1,394
includes taxes & fees
19 Nov - 20 Nov
Palm - Beach Houses Key West

Hammock House - Beach Houses Key West

Sugarloaf Key
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 €2,576
includes taxes & fees
24 Nov - 25 Nov
Hammock House - Beach Houses Key West

Azucar - Beach Houses Key West

Sugarloaf Key
10.0 out of 10, Exceptional, (10)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
The price is €2,145
includes taxes & fees
10 Dec - 11 Dec
Azucar - Beach Houses Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is €257
includes taxes & fees
20 Nov - 21 Nov
Aqua Lodges at Hurricane Hole Marina

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is €441
includes taxes & fees
19 Nov - 20 Nov
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (271)
"We will definitely stay here again. Perfect spot to relax. Clean Rooms "
United States
Gregory
Old Wooden Bridge Resort and Marina

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

Cudjoe Key
8.2 out of 10, Very good, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
The price is €280
includes taxes & fees
30 Nov - 1 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (158)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
The price is €281
includes taxes & fees
24 Nov - 25 Nov
Cottage with Pool and Dockage, just minutes to Key West

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.6 out of 10, Exceptional, (99)
"The house was very clean. Friendly and quiet location. The hosts were extremely helpful. "
United States
Roy F.
The price is €359
includes taxes & fees
19 Nov - 20 Nov
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key
9.0 out of 10, Wonderful, (88)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
Canal front, dockage, 2 bedroom, 2 bath

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key
9.8 out of 10, Exceptional, (120)
"We enjoyed our stay! Great little house and location. "
United States
Lisa K.
The price is €477
includes taxes & fees
20 Nov - 21 Nov
Kelly's Kabin - Adorable Private Summerland Key Cottage

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
Cudjoe Key
9.2 out of 10, Wonderful, (7)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is €521
includes taxes & fees
19 Nov - 20 Nov
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very good, (316)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is €250
includes taxes & fees
2 Dec - 3 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"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 €493
includes taxes & fees
3 Dec - 4 Dec
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Sands
The price is €503
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom house in Big Pine Key near Beach and Key West

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

Little Torch Key
9.6 out of 10, Exceptional, (85)
"The secluded dock is a nice feature. The driveway is tricky to exit. "
United States
drywall c.
The price is €616
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Old Town Key West
9.6 out of 10, Exceptional, (30)
"Nice, simple accomodation in a great location. There is a delightful deck just steps off the sidewalk to relax and enjoy the live music at the bar across the street. Also, quick beach access and decent street parking. Would definitely stay again."
United States
Kendra K.
The price is €333
includes taxes & fees
30 Nov - 1 Dec
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Cudjoe Key
9.8 out of 10, Exceptional, (26)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Living the Dream Key West Style

Stock Island
9.8 out of 10, Exceptional, (33)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
The price is €334
includes taxes & fees
16 Dec - 17 Dec
Living the Dream Key West Style
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

Find out more about Sugarloaf Key

Everything you need to know about Sugarloaf Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sugarloaf Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sugarloaf Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sugarloaf Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sugarloaf Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sugarloaf Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sugarloaf Key holiday rentals we have selected for you start as low as €250 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sugarloaf Key rentals

At Expedia, we put the best Sugarloaf Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sugarloaf Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sugarloaf Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sugarloaf Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.