Dredgers Key Holiday Rentals

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Holiday Rentals in Dredgers Key

Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, 333 reviews
"My husband and I came to Key West to celebrate our 30th anniversary. Ken's Studio was perfect. We knew it was small going in and so that didn't bother us. The location is outstanding as it is within walking distance of Duval Street and easy bike rides to the beach. The bikes were great for getting around KW, we rode them all over. The beach supplies (cooler, umbrella, chairs, snorkel equipment) were very much appreciated as well. Ken was an excellent host and was very good at communicating with...
The price is NZ$391
includes taxes & fees
20 Jun - 21 Jun
Steps from Duval, Pool & Bikes $129-$299 Night!
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, 99 reviews
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is NZ$447
includes taxes & fees
17 Jun - 18 Jun
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, 88 reviews
"Everyone was extremely nice and helpful."
The price is NZ$407
includes taxes & fees
13 Jun - 14 Jun
Aqua Lodges at Hurricane Hole Marina
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FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, 103 reviews
"Beautiful property in a great location. I would definitely stay again."
The price is NZ$462
includes taxes & fees
16 Jun - 17 Jun
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Poolside Cottage #411
10.0 out of 10, Exceptional, 17 reviews
"Clean. Everything we needed in a key west stay."
The price is NZ$600
includes taxes & fees
12 Jun - 13 Jun
Poolside Cottage #411
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
9.8 out of 10, Exceptional, 108 reviews
"I recently stayed at Azul Key West, and it was an absolutely incredible experience! The historic charm of the mansion, combined with modern amenities, created the perfect ambiance for a relaxing getaway. The location is unbeatable, just a short walk from Duval Street and the Hemingway House. The serene atmosphere and lush surroundings made it a true oasis. The staff were incredibly welcoming and attentive, ensuring our stay was comfortable and memorable. I highly recommend Azul Key West for...
The price is NZ$469
includes taxes & fees
12 Jun - 13 Jun
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
9.8 out of 10, Exceptional, 56 reviews
"Perfect, loved the pool area, very peaceful, beautiful property"
The price is NZ$734
includes taxes & fees
10 Jun - 11 Jun
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
COHIBA ~ Adults Only, Poolview 1 Bedroom Suite in Historic Azul Mansion!
9.6 out of 10, Exceptional, 102 reviews
"We were very happy with our stay! We recommend staying here."
The price is NZ$507
includes taxes & fees
3 Jul - 4 Jul
COHIBA ~ Adults Only, Poolview 1 Bedroom Suite in Historic Azul Mansion!
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, 95 reviews
"Wonderful stay. Was not in the room much, except to sleep and used the pool and common areas a few times and, overall, Azul was just beautiful and should I return, I would stay here again."
The price is NZ$458
includes taxes & fees
16 Jun - 17 Jun
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Salvador's Studio by Brightwild | Heated Pool!
8.0 out of 10, Very good, 20 reviews
"So enjoyed it ! Had never stayed in this part of Old Town , and this introduced me to so much. Would absolutely return."
The price is NZ$485
includes taxes & fees
26 Jun - 27 Jun
Salvador's Studio by Brightwild | Heated Pool!
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
9.0 out of 10, Wonderful, 214 reviews
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Penthouse Level Ocean Views- Live the Dream
9.6 out of 10, Exceptional, 210 reviews
"The penthouse was even more beautiful in person than shown in the photos! The view of the water was amazing, and there was plenty of space inside and on the (huge) balcony for me and my family to relax. Having access to the pool and private beach were also highlights, and it is conveniently located near Smathers Beach! The owners had everything setup and ready for us, and we had the best time! We will definitely be coming back!"
Penthouse Level Ocean Views- Live the Dream
Feb 3-10 $245 off the rates close beach full kitchen & patio
9.6 out of 10, Exceptional, 186 reviews
"We spent a week in Key West at this nice little main floor one bedroom suite. The location is great, and walkable to anywhere you might want to go in Key West. Parking was pretty easy...always found a spot within a 1/2 block. The area is safe and quiet, but really easy to get to all the great sites and the beaches. If you are considering a trip to Key West, Marilyn's place is a great place to stay. Thank you, Marilyn for having us!"
Feb 3-10 $245 off the rates close beach full kitchen & patio
Key West Beachfront Luxury 2/2 Condo A212
9.8 out of 10, Exceptional, 119 reviews
"Nice property with great furnishings; really liked that it felt more like a residence than a resort. I would stay here again if I had the chance."
Key West Beachfront Luxury 2/2 Condo A212
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, 204 reviews
"Beautiful and quiet location. Close to Key West yet just far enough to be away from the crowds. Family thoroughly enjoyed it. Everything is as pictured and immaculately clean, truly a gem. Melanie was friendly, always available and always responsive."
The price is NZ$623
includes taxes & fees
20 Jun - 21 Jun
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
9.6 out of 10, Exceptional, 41 reviews
"We spent a few nights here during a wedding weekend celebration in Key West. The home was in the perfect location. Very close to Duval street but set back enough for peace and quiet. The pool was amazing and much bigger than anticipated. The home was extremely roomy. All the amenities you would need and tons of towels! Highly recommend and will definitely stay here again!"
The price is NZ$3,528
includes taxes & fees
15 Jun - 16 Jun
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
Poolside Cottage #412
10.0 out of 10, Exceptional, 6 reviews
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
The price is NZ$600
includes taxes & fees
12 Jun - 13 Jun
Poolside Cottage #412
Steps To The Beach And The Sunrise-No Contact Check-In
9.4 out of 10, Exceptional, 95 reviews
"I rent a lot of VRBO’s and this is one of the best condos I have ever stayed at. It was very clean. It was very comfortable and I have to specifically comment on the beds. They were the most comfortable beds I’ve ever slept on in a condo. My friends said their bed was very very comfortable too. Also the location of this condo right by the pool is very convenient. And to sit on the patio and enjoy the wildlife out in the wetlands was very peaceful and enjoyable. I would rent his condo again."
Steps To The Beach And The Sunrise-No Contact Check-In
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, 25 reviews
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, 10 reviews
"The Yacht was beautiful. The marina was amazing. The marina and resort had excellent restaurants and bars. It was very cool to see all of the boats coming and going. It was an easy Uber ride to Key West and enjoy the fast pace life. Then it was wonderful to come back to the quiet of the marina. Would highly recommend a stay here."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
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See all available properties in Dredgers Key
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.

Other types of properties in Dredgers Key you may be interested in

Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, 1,542 reviews
"Oceans Edge was a great stay. The room and grounds were amazing. The pools were clean and stay did an great job. The onsite restaurant and bar was very nice but expensive. There are other places to eat on Stock Island, but they either require a car or bike. Fortunately, you revived received complimentary bike rentals daily from the resort if you wanted to grab breakfast or lunch. And the shuttle service to Key Island was on time, comfortable, and usually had available seating. It was about a $20...
The price is NZ$403
includes taxes & fees
10 Jun - 11 Jun
Oceans Edge Key West Resort, Hotel & Marina
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, 1,785 reviews
"Great service and great room!"
The price is NZ$451
includes taxes & fees
9 Jul - 10 Jul
Margaritaville Beach House Key West
Southernmost Beach Resort
4.0 star property
8.2 out of 10, Very good, 1,920 reviews
"All the people were very friendly and helpful. It was close to all the hot spots in old town. Would definitely stay again. "
The price is NZ$497
includes taxes & fees
10 Jun - 11 Jun
Southernmost Beach Resort
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Dredgers Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Dredgers Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Dredgers Key. Seeing all the best attractions is bound to make you fall in love with Dredgers Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Dredgers Key short-term rentals, that won’t be hard to do.

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