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Featured Condo Rentals in Sugarloaf Key and around

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (807)
"Very comfortable,clean and secure. Perfect location for all your needs. Unique in amenities. Nice swimming pool with spa. Marina was a pleasant surprise. Fishing is allowed. Our only disappointment was the toiletries. Very watered down and of poor quality. Next time we bring our own. We will be back each time we visit Key West. "
Coconut Mallory Resort And Marina By Kees Vacations

Chagall’s Corner | Newly Remodeled!

9.6 out of 10, Exceptional, (8)
"We enjoyed our stay. The place was nice and clean. It was exactly what we expected. "
The price is €474
includes taxes & fees
2 Apr - 3 Apr
Chagall’s Corner | Newly Remodeled!

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

9.8 out of 10, Exceptional, (77)
"Our room was perfect for the short stay.Finding a parking spot was a little challenging but once we found a spot and got settled we ventured out to explore the area.We will definitely recommend to our friends and family."
The price is €467
includes taxes & fees
31 Mar - 1 Apr
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

Duval Delight | Recently Remodeled Condo on Duval!

9.6 out of 10, Exceptional, (10)
"The property was exactly as deceived. Clean and right on Duval Street. We are coming. Ack in April and will try to stay here again. "
The price is €725
includes taxes & fees
27 Mar - 28 Mar
Duval Delight | Recently Remodeled Condo on Duval!

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

9.8 out of 10, Exceptional, (85)
"We had an amazing stay at Stripes for a girls trip. The house was clean and lovely and perfect for a group. We enjoyed the heated pool and the second floor balcony was a great place to enjoy a coffee in the morning or happy hour. The street was quiet but an easy walk to all of the entertainment of Duval Street. There is a great coffee shop around the corner which we enjoyed everyday. Everyone on the trip commented that they would stay there again. 10 out of 10!"
STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!

La Brisa - Ocean Views Across from Smathers Beach

10.0 out of 10, Exceptional, (123)
"Excellent, we will stay everytime we come to Keywest. Love the view. Would not stay anywhere else.The owner was very helpful and got back to us quickly anytime we needed anything! The condo was quiet, and the others at the condo were quiet and thoughtful of everyone staying there!"
La Brisa - Ocean Views Across from Smathers Beach

Tranquility by Smathers and 10 minute bike downtown Key West value savings

9.4 out of 10, Exceptional, (106)
"The property was very clean, is convenient to Key West “Old Town” and is adjacent to the airport. My wife and I stayed there with friends. We used the 2nd bedroom and our friends used the master. Bedding in the 2nd bedroom isn’t great, but was okay for a short stay. If I owned the unit I would definitely update the mattress in the 2nd bedroom. The unit needs some repairs, especially to the closet doors. The closet doors in the master br were the only ones that closed properly. One funny...
Tranquility by Smathers and 10 minute bike downtown Key West value savings

Private Parking & Near Downtown - Sea Breeze

9.4 out of 10, Exceptional, (36)
"Excellent location -you really can’t do better. Management company is excellent and readily available. Linens and kitchen equipment all plentiful. We had a problem with the refrigerator and it was promptly dealt with. Would def stay here again. "
The price is €740
includes taxes & fees
1 Apr - 2 Apr
Private Parking & Near Downtown - Sea Breeze

Oceanfront Marina Condo With All Luxuries

9.8 out of 10, Exceptional, (140)
"I stay here, if available when visiting Key West. The condo is fantastic, the location is superb."
Oceanfront Marina Condo With All Luxuries

Leo’s Lodge | Newly Updated!

8.0 out of 10, Very good, (4)
"The property is well maintained. The room and property were clean. Staff is top notch and very helpful with any need. Highly recommend this property! Close to deval and the night life."
The price is €343
includes taxes & fees
23 Mar - 24 Mar
Leo’s Lodge | Newly Updated!

Penthouse Beach Ocean Views- Live the Dream

9.6 out of 10, Exceptional, (233)
"We thoroughly enjoyed the condo, its surroundings and location. Pool, beach area and convenient location to Smathers beach were excellent! Unit was very clean and well furnished. Beds were a little firm for our liking, but unit was very clean and well stocked. We can't wait to return!"
Penthouse Beach Ocean Views- Live the Dream

Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi

10.0 out of 10, Exceptional, (287)
"Shipyard condos is the place to be in Key West. It’s a quiet peaceful community in the Truman Annex yet just three blocks from Duval. This condo is perfect for a couple with one bedroom on bath. Fully equipped with a lovely deck off the Living area. You’re just steps away from the community pool. The condo comes with two bikes for your use. Highly recommended!"
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi

Galleon Resort beach hotel luxury in Old Town Key West

9.8 out of 10, Exceptional, (126)
"Fantastic rental! Easy check in process. The resort location is perfect to the wharf, bars, and restaurants. The unit was spotless and decorated with tropical vibes. Bed was comfortable, kitchen had everything you needed for your stay.. Ed is a great host."
Galleon Resort beach hotel luxury in Old Town Key West

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

9.4 out of 10, Exceptional, (74)
"Enjoyed our short stay - only negative was the connecting door / noise transmission with the adjoining unit"
The price is €498
includes taxes & fees
6 Apr - 7 Apr
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Luxury Waterfront at Galion Resort in Old Town

9.6 out of 10, Exceptional, (81)
"The only complaint would be the garden tub. Very hard to get in to get a shower!!! Especially when you have short legs"
Luxury Waterfront at Galion Resort in Old Town

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

9.6 out of 10, Exceptional, (122)
"The property was lovely and very peaceful and quiet. It was delightful to take a dip in the warm pool after a busy day at Dry Tortugas N.P. or mid-day between shopping and going to dinner. The kitchen was very convenient for preparing a light breakfast or lunch"
The price is €346
includes taxes & fees
13 Mar - 14 Mar
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

Ocean Front Presidential Suite | Beachside Resort

10.0 out of 10, Exceptional, (2)
"Our 3-bedroom suite was spacious and we loved the fact that there was a washer/dryer in the suite and a well stocked kitchen. The heated pool was great! Parking convenient."
The price is €1,111
includes taxes & fees
1 Apr - 2 Apr
Ocean Front Presidential Suite | Beachside Resort

Andy’s Attic | Budget-Friendly!

9.0 out of 10, Wonderful, (6)
"Good experience overall nice to have a kitchenette pool area was lovely"
The price is €345
includes taxes & fees
19 Mar - 20 Mar
Andy’s Attic | Budget-Friendly!

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

9.4 out of 10, Exceptional, (3)
"Great accommodations. Perfect location."
The price is €576
includes taxes & fees
2 Apr - 3 Apr
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!

Private Balcony & Parking - Villa Positano

8.2 out of 10, Very good, (10)
"Very nice and clean property in a fantastic location,"
The price is €791
includes taxes & fees
23 Mar - 24 Mar
Private Balcony & Parking - Villa Positano
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

2.5 star property
8.4 out of 10, Very good, (197)
"Our space was nice and the woman was nice and friendly. There were many deer walking through. We didn't spend a lot of time at the property as we were out exploring Key West and other beaches."
The price is €245
includes taxes & fees
16 Mar - 17 Mar
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (121)
"We enjoyed the small deck that allowed us to watch the boat activity. The shower was so slick it was dangerous to use. It was a little inconvenient to either walk on the short gravel path or walk on the decking and step over all the hoses that were used by the fishing boats. Overall, it was about what we expected from the web site description."
The price is €413
includes taxes & fees
20 Mar - 21 Mar
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (375)
"Thank you"
Steps from Duval, Pool on Site & Bikes Included!
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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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.