Lower Sugarloaf Key Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Vacation Rentals in Lower Sugarloaf Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (253)
"I love ❤️ this place "
The price is CA $146
CA $359 total
includes taxes & fees
Sep 1 - Sep 2
Old Wooden Bridge Resort and Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (307)
"We had a nice stay. The property was in a great location."
The price is CA $313
CA $391 total
includes taxes & fees
Sep 3 - Sep 4
Hyatt Vacation Club at Sunset Harbor, Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"The stay was beautiful "
The price is CA $81
CA $323 total
includes taxes & fees
Aug 11 - Aug 12
Aqua Lodges at Hurricane Hole Marina

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is CA $134
CA $458 total
includes taxes & fees
Aug 12 - Aug 13
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (393)
"this was exactly as advertised and close to all the action"
The price is CA $123
CA $314 total
includes taxes & fees
Aug 4 - Aug 5
Steps from Duval, Pool on Site & Bikes Included!

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

7.4 out of 10, Good, (10)
"We were here celebrating 55th birthdays and had a blast. Great location and communication with Capt. We will return for sure, hoping to make it an annual get together."
The price is CA $385
CA $1,020 total
includes taxes & fees
Aug 11 - Aug 12
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

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

9.6 out of 10, Exceptional, (77)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is CA $414
CA $962 total
includes taxes & fees
Aug 18 - Aug 19
Old Florida Style, wrap around porch, boat basin for dockage, open water

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (138)
"We stayed in the Cohiba and it was so cute! Felt private and to ourselves. Everyone we met on site was so friendly. Having the pool on property and private was such a blessing. There was an incident in the main house bathroom that was quickly responded to by property management. Would stay again! Thank you! "
The price is CA $136
CA $347 total
includes taxes & fees
Aug 4 - Aug 5
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (133)
"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"
Heart of Downtown Key West Cottage With Off-Street Parking

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (13)
"Property was cute ... cleanly and in a great location for what we were looking for. Would definitely recommend to anyone and stay there again ourselves "
The price is CA $181
CA $583 total
includes taxes & fees
Aug 4 - Aug 5
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

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

9.6 out of 10, Exceptional, (141)
"Very clean, great location and wonderful amenities!"
The price is CA $131
CA $340 total
includes taxes & fees
Aug 6 - Aug 7
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay at the Delaney house. The pool and outdoor area were lovely and private, the location was excellent and walking distance from fun Key West spots but quiet and cozy, and the beds were all incredibly comfortable! Would definitely recommend this place to everyone!"
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (178)
"Place is centrally located which is ideal for walking from place to place. House was very clean and had everything needed for my time spent there"
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (19)
"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."
The price is CA $134
CA $461 total
includes taxes & fees
Aug 4 - Aug 5
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!

Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

9.6 out of 10, Exceptional, (8)
"The units were perfect and the customer service was amazing. "
The price is CA $372
CA $1,168 total
includes taxes & fees
Aug 31 - Sep 1
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (7)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
The price is CA $223
CA $372 total
includes taxes & fees
Aug 7 - Aug 8
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

10.0 out of 10, Exceptional, (18)
"Will stay here again "
The price is CA $134
CA $461 total
includes taxes & fees
Aug 4 - Aug 5
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

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

9.8 out of 10, Exceptional, (295)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

9.2 out of 10, Wonderful, (10)
"Great time staying there "
The price is CA $121
CA $327 total
includes taxes & fees
Aug 12 - Aug 13
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Lower Sugarloaf Key Hotel Reviews