Holiday Rentals in Lower Sugarloaf Key

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Lower Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (161)
"Loved this stay!!! May not be for everyone but we loved the rustic feel and being away from the crowds!!! The staff was very friendly and our cabin on the water was comfy and cozy! Would definitely stay again. "
The price is €235
includes taxes & fees
25 Nov - 26 Nov
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (104)
"Nice for affordable price "
The price is €268
includes taxes & fees
5 Dec - 6 Dec
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (356)
"We walked most everywhere and loved the Southernmost Beach Bar! Eating at Moon Dog Cafe was so spectacular that we ate there 3 times in 2 days! This place is all it says it is. Simply perfect. "
The price is €235
includes taxes & fees
2 Dec - 3 Dec
Steps from Duval, Pool on Site & Bikes Included!

Poolside Cottage #411

10.0 out of 10, Exceptional, (30)
"Nice location very close to everything and close enough to Duval St. Unit itself was in good condition and the kitchen stocked pretty good but was missing dish cloths, dish towels and dishwasher detergent. None of the grills on the property were functional. Host was very responsive the entire process. Would stay there again"
The price is €375
includes taxes & fees
2 Dec - 3 Dec
Poolside Cottage #411

34’ Catamaran Sailboat

9.6 out of 10, Exceptional, (27)
"Overall it was a great experience."
34’ Catamaran Sailboat

SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

10.0 out of 10, Exceptional, (14)
"BOOK THIS BOAT!!!’ TOP 10 vacations ever!!! Hannah was so accommodating and onboarded us to The Grand Admiral. Beautiful marina with easy access to The Perry hotel and bar, making it a very very comfortable stay. And then the excursion 😍!! Captain Jeff made our day exceptional. We encountered dolphins, lounged on the sandbar, and grilled while watching a breathtaking sunset. We will be making this an annual trip! Thank you Captain Jeff for the best day ever."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!

TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

9.2 out of 10, Wonderful, (165)
"We found the tides on Simonton online and booked it immediately. When we arrived, the check-in process was very easy and the location is very nice. We ate down the street at Duffys twice during our stay and it is an amazing place. I highly recommend their prime rib. we will definitely be back "
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!

Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

9.4 out of 10, Exceptional, (214)
"Very clean. Could use some updating such as fresh paint. "
The price is €430
includes taxes & fees
26 Nov - 27 Nov
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

9.0 out of 10, Wonderful, (202)
"Close to Duval Street and within walking distance to everything. Full kitchen is nice. Good for a Key West visit. "
The price is €271
includes taxes & fees
11 Dec - 12 Dec
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

9.4 out of 10, Exceptional, (112)
"Quit little place."
The price is €338
includes taxes & fees
26 Nov - 27 Nov
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

9.2 out of 10, Wonderful, (238)
"Place was very comfortable-great for couples who "
The price is €574
includes taxes & fees
27 Nov - 28 Nov
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

9.0 out of 10, Wonderful, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Heart of Old Town getaway, perfect romantic retreat - near the action

9.0 out of 10, Wonderful, (38)
"Good"
The price is €359
includes taxes & fees
8 Dec - 9 Dec
Heart of Old Town getaway, perfect romantic retreat - near the action

Feb 3-10 $245 off the rates close beach full kitchen & patio

9.6 out of 10, Exceptional, (200)
"Very walkable. Cozy comfortable place. Cute and safe neighborhood. Setup well for cooking. AC pumps some good cold air. "
Feb 3-10 $245 off the rates close beach full kitchen & patio

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (216)
"Property was clean and had everything to have an enjoyable stay."
The price is €706
includes taxes & fees
25 Nov - 26 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (171)
"Room fit our needs. small, but very clean. Location was great! "
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

9.0 out of 10, Wonderful, (222)
"Nice place ,great ammenties very close to duval street, cuban place right on the corner by it is great "
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

The Crystalmarine Suite – Rustic Luxury on the Sea

10.0 out of 10, Exceptional, (2)
"This VRBO is a dream for those looking to escape the hustle and bustle of everyday life. With its unique location, it provides a perfect blend of adventure and relaxation. Whether you're looking to reconnect with nature or simply unwind in a beautiful setting, this floating house offers an unparalleled experience."
The price is €874
includes taxes & fees
8 Dec - 9 Dec
The Crystalmarine Suite – Rustic Luxury on the Sea

CORONA ~ Adults Only, King Suite with Community Pool at Azul Mansion!

9.8 out of 10, Exceptional, (127)
"Parking on site. The property manager is amazing! Very quiet house, located near everything. "
The price is €336
includes taxes & fees
25 Nov - 26 Nov
CORONA ~ Adults Only, King Suite with Community Pool at Azul Mansion!

FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!

9.4 out of 10, Exceptional, (106)
"Not bad comfortable room was a little smaller then expected bathroom was clean no daily maid cleaning there is a service charge for cleaning though ?? Pool area looks rundown cleaning required probably i didnt use the pool anyway overall property was somwhat quiet other then person upstairs was not considerate to other i would recommend this property."
The price is €328
includes taxes & fees
27 Nov - 28 Nov
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!
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.
Don't see what you're looking for?
See all available properties in Lower Sugarloaf Key
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Lower Sugarloaf Key you may be interested in

Southernmost Beach Resort

4.0 star property
8.6 out of 10, Excellent, (2190)
"No me gustó q en expedia no explicara q no incluya el estacionamiento "
The price is €327
includes taxes & fees
17 Dec - 18 Dec
Southernmost Beach Resort

Havana Cabana at Key West - Adults Only

4.0 star property
8.8 out of 10, Excellent, (1615)
"Great property!!!"
The price is €209
includes taxes & fees
18 Dec - 19 Dec
Havana Cabana at Key West - Adults Only

Margaritaville Beach House Key West

4.0 star property
8.6 out of 10, Excellent, (1799)
"Quality place "
The price is €281
includes taxes & fees
19 Dec - 20 Dec
Margaritaville Beach House Key West
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.