Sugarloaf Key Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Sugarloaf Key

Our top choices for Sugarloaf Key vacation rentals

Old Wooden Bridge Resort and Marina
2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (257)
"River boat houses, pool, kayak rentals. "
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, (161)
"The stay was beautiful "
The price is ￥14,303
￥16,091 total
includes taxes & fees
Sep 1 - Sep 2
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Exterior

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (312)
"EXCELENT LOCATION AND SUNSET VIEW"
The price is ￥35,762
￥44,380 total
includes taxes & fees
Sep 3 - Sep 4
Hyatt Vacation Club at Sunset Harbor, Key West
Steps from Duval, Pool on Site & Bikes Included!
Exterior

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (397)
"this was exactly as advertised and close to all the action"
The price is ￥13,122
￥32,915 total
includes taxes & fees
Sep 4 - Sep 5
Steps from Duval, Pool on Site & Bikes Included!
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Beach nearby

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

9.6 out of 10, Exceptional, (140)
"This property was great, it had everything needed, extremely clean and walking distance to Davual st.The pool area is wonderful and it was the perfect temperature!Would highly recommend."
The price is ￥13,991
￥35,678 total
includes taxes & fees
Sep 2 - Sep 3
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
Beach nearby

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

9.4 out of 10, Exceptional, (11)
"Great time staying there "
The price is ￥12,960
￥34,370 total
includes taxes & fees
Sep 2 - Sep 3
WHITEHEAD ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

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

9.6 out of 10, Exceptional, (78)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water
THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
Beach nearby

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

9.8 out of 10, Exceptional, (18)
"Great place will rent again "
The price is ￥12,960
￥34,370 total
includes taxes & fees
Sep 4 - Sep 5
THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & Shared Pool
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Exterior

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (181)
"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!
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
1 bedroom, free WiFi, bed sheets

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

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay here with our kids. Can’t beat the location."
The price is ￥11,929
￥46,075 total
includes taxes & fees
Sep 9 - Sep 10
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Claude Monet Suite | Cozy Studio with Pool & Patio Access!
Terrace/patio

Claude Monet Suite | Cozy Studio with Pool & Patio Access!

9.4 out of 10, Exceptional, (20)
"Great location. Everything was perfect!"
The price is ￥12,223
￥38,335 total
includes taxes & fees
Sep 24 - Sep 25
Claude Monet Suite | Cozy Studio with Pool & Patio Access!
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!
Beach nearby

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!

9.2 out of 10, Wonderful, (16)
"I was initially worried because I normally would only book with a property that had quite a bit of reviews. I'm glad I trusted my instincts to go with the Inn on Fleming! The room looked exactly as pictured. The whole lodge had a cute charm to it. Perfect place to stay when visiting the keys."
The price is ￥18,261
￥42,580 total
includes taxes & fees
Sep 4 - Sep 5
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite w/Shared Pool!
Heart of Downtown Key West Cottage With Off-Street Parking
Exterior

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (134)
"May not be a better location"
Heart of Downtown Key West Cottage With Off-Street Parking
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
Exterior detail

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

9.6 out of 10, Exceptional, (15)
"Great place to stay! Very clean and steps to Duval Ave."
The price is ￥14,432
￥55,584 total
includes taxes & fees
Sep 10 - Sep 11
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
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, (296)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (55)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: great place, great location! we'll be back year after year!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
Beach

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

9.6 out of 10, Exceptional, (188)
"The location was perfect for exploring and getting places in key West. It had a relaxing vibe that was perfect for vacation. "
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
Beach nearby

ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!

9.6 out of 10, Exceptional, (131)
"This was a clean property which had everything including an ice machine and filttered water machine! Friendly professional people who work there and have thought of every extra touch to make your stay worry free! Great pool,and I stayed at the top "treehouse" room which had 2 sets of stairs to get to it. It was a large room and I enjoyed it with my own private deck!"
The price is ￥14,432
￥36,763 total
includes taxes & fees
Sep 9 - Sep 10
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
Terrace/patio

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 ￥37,848
￥123,497 total
includes taxes & fees
Sep 7 - Sep 8
Southernmost Retreat | On Duval! With Hot Tub, Patio, & Private Parking
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
A heated pool

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

9.8 out of 10, Exceptional, (44)
"Wonderful view, lot's of space, great location "
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
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

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