Lower Sugarloaf Key Holiday Rentals

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
22 Jan - 23 Jan
Tomorrow
23 Jan - 24 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

Holiday Rentals in Lower Sugarloaf Key

Old Wooden Bridge Resort and Marina
Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (179)
"Our stay in cabin 9 (turquoise one) was great. This cabin was perfect for our needs and we brought two dogs with us, no issues with that. We loved our stay but to be transparent this is really no frills. There is no sink sponge, no aluminum foil no nothing extra in the kitchen so bring your own!! The mattresses are VERY firm. There were a few small cosmetic issues that could be addressed in this cabin that would make a huge difference, example, crooked drawer front in kitchen, pinned drapes...
The price is HK$1,004
HK$1,907 total
includes taxes & fees
26 Jan - 27 Jan
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (112)
"We loved staying on the houseboat."
The price is HK$1,183
HK$2,425 total
includes taxes & fees
28 Jan - 29 Jan
Aqua Lodges at Hurricane Hole Marina
Steps from Duval, Pool on Site & Bikes Included!
Beach towels

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (361)
"Fun little place with a great pool. Ken was very helpful in all aspects. Highly recommended. Be aware its a small place but very comfortable."
The price is HK$1,394
HK$2,660 total
includes taxes & fees
3 Feb - 4 Feb
Steps from Duval, Pool on Site & Bikes Included!
34’ Catamaran Sailboat
Interior

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (30)
"We had a wonderful time. It is an older, smaller boat but we enjoyed it. There is a port a pot in the cabin but there is a huge shower and bathroom under the carport. We were able to fish right off the boat. Frank will answer texts pretty quickly. "
34’ Catamaran Sailboat
Poolside Cottage #411
Outdoor dining

Poolside Cottage #411

10.0 out of 10, Exceptional, (36)
"Great little condo - perfect for our family to visit Key West! "
The price is HK$1,892
HK$3,143 total
includes taxes & fees
28 Jan - 29 Jan
Poolside Cottage #411
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (169)
"It was kind of exciting. the cops showed up on the property and on the next door property to the North, there was a tree of stolen bouys and a stolen crab trap. It was quiet. there was a bit of a flood when it rained but within a day or 2 the water was gone. we had trouble opening the slider on the deck and I think there was moisture in the door. Hopefully we left it pretty clean. we had to be at the airport by 6:30. thank you, it was a wonderful stay. Patty "
Direct Oceanfront Cottage-Sunrise View- #2,
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds

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

9.8 out of 10, Exceptional, (16)
"Staying on the Grand Admiral was really awesome for my wife and I. The location at Perry Marina was exceptional. The whole process was very easy, working with Kathy for booking, Stephanie for check-in and Captain John for our charter, everything went smooth. "
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!
Beach nearby

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

9.6 out of 10, Exceptional, (118)
"We had a great time. Enjoyed the property very much."
The price is HK$3,410
HK$5,303 total
includes taxes & fees
10 Feb - 11 Feb
HAVANA VIEJA ~ Adults Only, Poolside Queen Suite w/ Shared Pool!
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!
Miscellaneous

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

9.4 out of 10, Exceptional, (111)
"Great location!"
The price is HK$1,526
HK$2,911 total
includes taxes & fees
29 Jan - 30 Jan
FONTANA ~ Adults Only, Pool Access King Suite at Azul Mansion!
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (205)
"I recently stayed at this property and had a generally pleasant experience. The property itself is nice and well-maintained, with a great location that adds to its appeal. The surrounding area is excellent, making it convenient and enjoyable. However, there were a few downsides to my stay. The internet was not working, which was quite inconvenient. Additionally, while the property is good overall, it could benefit from having a few more amenities. The bathroom, in particular, could use some...
The price is HK$2,242
HK$4,162 total
includes taxes & fees
20 Feb - 21 Feb
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

The Caroline Suite | 1 bed, 1 bath condo w/shared pool

9.4 out of 10, Exceptional, (12)
"Place was clear, ready, and in a great area. If your looking for a good place in key west this is it"
The price is HK$3,073
HK$5,332 total
includes taxes & fees
23 Jan - 24 Jan
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
The Crystalmarine Suite – Rustic Luxury on the Sea
Interior

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 HK$5,446
HK$6,905 total
includes taxes & fees
27 Jan - 28 Jan
The Crystalmarine Suite – Rustic Luxury on the Sea
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (215)
"Very clean. Could use some updating such as fresh paint. "
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Aerial view

Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort

9.6 out of 10, Exceptional, (82)
"Great trip with 16 people for a 50th birthday party. Host was very helpful and informative throughout the trip. Great for large groups."
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
A heated pool

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

9.8 out of 10, Exceptional, (117)
"This has been our go to place to stay while in the keys. We love the pool, hot tub and beach. My boys can walk right out into the beach and start fishing. It is out of the hustle and bustle but not too far out. Highly recommend!"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (221)
"Everything was very nice. We enjoyed sitting down by the water any time. It was close to everything we were interested in seeing and doing. Great stay."
The price is HK$3,309
HK$7,057 total
includes taxes & fees
20 Feb - 21 Feb
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Bahama Village studio @ the Galleria!
Pool

Bahama Village studio @ the Galleria!

9.6 out of 10, Exceptional, (10)
"Everything was as advertised. Its location was fantastic with easy access on foot to everything Key West has to offer. Only negative is that there is a high top table and two chairs in a space that really doesn’t afford those niceties. The bed was comfortable. The ac was a bit loud."
Bahama Village studio @ the Galleria!
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Outdoor pool, a heated pool

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (280)
"We had a wonderful week during the Christmas/ New Year break. The condo is exceptional. Very clean including many items that make your stay easy and welcoming. The kitchen is fully stocked, not that one needs much while staying on the island. We relaxed in the condo, enjoyed restaurants and music across the island. "
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Luxury 62' Yacht! In a Beautiful Resort
Outdoor pool, a heated pool

Luxury 62' Yacht! In a Beautiful Resort

10.0 out of 10, Exceptional, (7)
"Excellent boat, excellent stay. Would love to return."
Luxury 62' Yacht! In a Beautiful Resort
Unique Home with loft @ Truman Annex
Beach nearby

Unique Home with loft @ Truman Annex

9.8 out of 10, Exceptional, (113)
"Not a single issue, very responsive"
Unique Home with loft @ Truman Annex
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
Sign in
Sign up, it's free

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

Havana Cabana at Key West - Adults Only
Outdoor pool, pool loungers

Havana Cabana at Key West - Adults Only

4.0 star property
8.8 out of 10, Excellent, (1648)
"It was pretty noisy near the pool at night, but super fun during the day! "
The price is HK$1,846
HK$2,580 total
includes taxes & fees
26 Jan - 27 Jan
Havana Cabana at Key West - Adults Only
Ibis Bay Beach Resort
Outdoor pool, pool umbrellas, pool loungers

Ibis Bay Beach Resort

2.5 star property
8.0 out of 10, Very good, (1721)
"Didn’t have regular TV."
The price is HK$1,919
HK$2,368 total
includes taxes & fees
26 Jan - 27 Jan
Ibis Bay Beach Resort
Southernmost Beach Resort
3 outdoor pools, pool umbrellas, pool loungers

Southernmost Beach Resort

4.0 star property
8.6 out of 10, Excellent, (2237)
"First time visiting key west and I absolutely loved the southernmost beach resort was in a perfect location with so much to do on and near by the property!!!"
The price is HK$3,846
HK$4,851 total
includes taxes & fees
3 Feb - 4 Feb
Southernmost Beach Resort
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.