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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Featured Condo Rentals in Sugarloaf Key

Coconut Mallory Resort And Marina By Kees Vacations
2 outdoor pools

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (808)
"Very tropical, on the water. Everything u need in amenities. Pools were great!"
Coconut Mallory Resort And Marina By Kees Vacations
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Beach nearby

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

9.6 out of 10, Exceptional, (130)
"We had a great time. Enjoyed the property very much."
The price is NZ$481
includes taxes & fees
6 May - 7 May
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!
Interior

THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!

9.2 out of 10, Wonderful, (7)
"The place looks even better in person. Pictures don’t do it justice! Super clean and cozy. The entire place is maintained very well. The only tiny issue we had while staying there was the slow internet.Enjoy our stay & highly recommended!"
The price is NZ$501
includes taxes & fees
5 May - 6 May
THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
Flat-screen TV, DVD player, stereo

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (173)
"We would definitely stay here again! Great location, exactly as described, overall great place."
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!
AMBROSIA ~ Adults Only, Poolside King Room in Azul Mansion!
Miscellaneous

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

9.4 out of 10, Exceptional, (107)
"Was great "
The price is NZ$595
includes taxes & fees
8 May - 9 May
AMBROSIA ~ Adults Only, Poolside King Room in Azul Mansion!
STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!
Exterior

STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!

9.8 out of 10, Exceptional, (88)
"Place was awesome, would definitely stay there again"
STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
A heated pool

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

9.2 out of 10, Wonderful, (131)
"Place was great. "
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!
Terrace/patio

THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!

9.4 out of 10, Exceptional, (8)
"Great accommodations. Perfect location."
The price is NZ$601
includes taxes & fees
4 May - 5 May
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
A heated pool

GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!

9.8 out of 10, Exceptional, (81)
"We had a great stay. Loved the location. Location made it easy for us to walk everywhere. Very quiet & relaxing. Pool felt private. Everything was clean"
The price is NZ$658
includes taxes & fees
5 May - 6 May
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
A heated pool

Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!

8.6 out of 10, Excellent, (11)
"Small unit but it’s all we need and everything advertised "
The price is NZ$600
includes taxes & fees
14 May - 15 May
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!
Beach nearby

FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!

9.8 out of 10, Exceptional, (124)
"Great location "
The price is NZ$524
includes taxes & fees
5 May - 6 May
FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!
Leo’s Lodge | Newly Updated!
A heated pool

Leo’s Lodge | Newly Updated!

8.2 out of 10, Very good, (11)
"Bery mice pkace clean and quiet close to Duvall street"
The price is NZ$603
includes taxes & fees
4 May - 5 May
Leo’s Lodge | Newly Updated!
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Beach nearby

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

9.8 out of 10, Exceptional, (105)
"Excellent location, walkable to Duval Street. We were able to park on-site and walk to everything. We would definitely stay here again."
The price is NZ$498
includes taxes & fees
4 May - 5 May
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Beach nearby

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

9.4 out of 10, Exceptional, (79)
"Property was wonderful and pricing was lower than all other location on the busy New Year’s time frame. Pool are was secluded and peaceful "
The price is NZ$684
includes taxes & fees
21 May - 22 May
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Spectacular Morning Sunrises, Smathers Beach convenience La Brisa 3 Bedroom.
Beach/ocean view

Spectacular Morning Sunrises, Smathers Beach convenience La Brisa 3 Bedroom.

9.8 out of 10, Exceptional, (7)
"The place was great - had most everything we needed. Location was ideal across the street from the beach. Pool and tennis court were both great. "
Spectacular Morning Sunrises, Smathers Beach convenience La Brisa 3 Bedroom.
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, (286)
"Great time!! Great place!!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Key West Beachfront Luxury 2/2 Condo A212
Outdoor pool, a heated pool

Key West Beachfront Luxury 2/2 Condo A212

10.0 out of 10, Exceptional, (146)
"Great location! Pool area and a short walk to the beach were exactly what we were looking for."
Key West Beachfront Luxury 2/2 Condo A212
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Beach nearby

SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!

9.8 out of 10, Exceptional, (78)
"Loved the property, pool area and location!"
The price is NZ$758
includes taxes & fees
1 May - 2 May
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Interior

ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath

9.8 out of 10, Exceptional, (45)
"This is an amazing property in an amazing location. "
The price is NZ$1,562
includes taxes & fees
6 May - 7 May
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Luxury Waterfront at Galion Resort in Old Town
Terrace/patio

Luxury Waterfront at Galion Resort in Old Town

9.6 out of 10, Exceptional, (80)
"Great location and very nice place "
The price is NZ$1,442
includes taxes & fees
4 May - 5 May
Luxury Waterfront at Galion Resort in Old Town
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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Other property types in Sugarloaf Key

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

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (223)
"Lovely, quiet place on the water with plenty of space in the houseboat"
The price is NZ$432
includes taxes & fees
1 May - 2 May
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (134)
"Would definitely stay here again! "
The price is NZ$554
includes taxes & fees
5 May - 6 May
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Sunset Harbor, Key West
Outdoor pool

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very good, (295)
"We had a nice stay. The property was in a great location."
The price is NZ$578
includes taxes & fees
4 May - 5 May
Hyatt Vacation Club at Sunset Harbor, 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.

Frequently asked questions

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.