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Featured Condo Rentals in Sugarloaf Key and around

Our top choices for Sugarloaf Key condo rentals

SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool

9.8 out of 10, Exceptional, (20)
"The Inn was very well kept, very quiet, comfortable, and clean. We enjoyed our stay very much and it was in a great location. "
The price is €311
includes taxes & fees
21 Oct - 22 Oct
SIMONTON ROOM @ Inn on Fleming~ADULTS ONLY 1st Lvl King w/Shared Heated Pool

SUMMER ISN'T OVER YET - PRICES REDUCED FOR OPEN NIGHTS!!!!

9.4 out of 10, Exceptional, (205)
"wonderful place to stay"
SUMMER ISN'T OVER YET - PRICES REDUCED FOR OPEN NIGHTS!!!!

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

9.6 out of 10, Exceptional, (146)
"We had a great stay places is amazing"
The price is €336
includes taxes & fees
20 Oct - 21 Oct
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

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

9.8 out of 10, Exceptional, (157)
"Place was clean and had everything we needed to explore key west"
The price is €393
includes taxes & fees
21 Oct - 22 Oct
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

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

9.4 out of 10, Exceptional, (132)
"Over perfect. A couple blocks from good eats and beaches. Couldn’t have been more pleased"
FONTANA ~ Adults Only, Pool Access King Room at Azul Mansion!

Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK

9.0 out of 10, Wonderful, (121)
"Very nice place to stay. We really enjoyed our visit. Would recommend for anyone visiting Key West. "
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (819)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

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

9.8 out of 10, Exceptional, (129)
"Beautiful property & great location with stunning views. "
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

9.8 out of 10, Exceptional, (212)
"perfect for families with young kids"
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

Direct Ocean View from Your Condo-No Contact Check-In

9.4 out of 10, Exceptional, (161)
"The condo was perfect!!! Close to everything yet far enough away to enjoy quiet evenings on the balcony. Pool was clean. Grounds are beautiful. We look forward to staying here next year!! "
Direct Ocean View from Your Condo-No Contact Check-In

COCONUT PALM STUDIO ~ Adult Only Studio, Heated Shared Pool & Close to Town!

9.6 out of 10, Exceptional, (93)
"Very secluded feel to this place. When in the pool, you feel like you are in an oasis on a tropical Caribbean island! Loved this place. Will definitely stay here for our next visit."
COCONUT PALM STUDIO ~ Adult Only Studio, Heated Shared Pool & Close to Town!

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (182)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

9.2 out of 10, Wonderful, (17)
"My brother and I decided to take a weekend trip to Key West and the Fleming Inn was perfect for our stay. Beds are comfortable. Rooms were nice and cool. Plenty of amenities for eating in. I loved our little balcony for drinking coffee in the morning. Plus we were just a short walk to all the fun stuff. I would definitely stay here again. "
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor & Shared Heated Pool

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

9.6 out of 10, Exceptional, (19)
"Great place will rent again "
TRUMAN ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen & Shared Heated Pool

AMBROSIA ~ Adults Only, Poolside King Room in Azul Mansion!

9.4 out of 10, Exceptional, (117)
"Was great "
The price is €368
includes taxes & fees
21 Oct - 22 Oct
AMBROSIA ~ Adults Only, Poolside King Room in Azul Mansion!

Luxury Waterfront at Galion Resort in Old Town

9.6 out of 10, Exceptional, (91)
"Enjoyed our stay at Galleon"
Luxury Waterfront at Galion Resort in Old Town

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

9.0 out of 10, Wonderful, (16)
"Nice location. Near restaurants and shopping. Pool perfect mid day. Unit clean. "
The price is €676
includes taxes & fees
21 Oct - 22 Oct
The Caroline Suite | 1 bed, 1 bath condo w/shared pool

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

9.6 out of 10, Exceptional, (141)
"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 €207
includes taxes & fees
24 Sept - 25 Sept
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

9.6 out of 10, Exceptional, (17)
"Short walk to Duval street, quiet and very clean and comfortable."
The price is €202
includes taxes & fees
23 Sept - 24 Sept
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

CORNISH SUITE @ Inn on Fleming ADULTS ONLY 3rd Floor 2 BR /Shared Heated Pool

9.0 out of 10, Wonderful, (16)
"Would definitely stay again or recommend "
The price is €416
includes taxes & fees
21 Oct - 22 Oct
CORNISH SUITE @ Inn on Fleming ADULTS ONLY 3rd Floor 2 BR /Shared Heated Pool
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

Find out more about Sugarloaf Key

Sugarloaf Key Condo Rentals information

Number of reviews
2,229
Accommodation
379 Condo Rentals
Lowest Price
€202
Highest Price
€676

Frequently asked questions

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What is there to do in Sugarloaf Key near my condo?
The most useful travel accessory is a well-planned to-do list. Florida Keys Beaches is a wonderful place to begin your exploration of Sugarloaf Key.