Dredgers Key Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Dredgers Key Vacation Homes

Fridge, microwave, oven, stovetop
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
10.0 out of 10, Exceptional, (1)
"We had a great time at Pagitt House. The location is central to everything you’d want to do in Key West. The rooms are comfortable and well appointed. We didn’t use the kitchen much but it was well stocked with whatever you might need."
The price is CA $681
CA $1,803 total
includes taxes & fees
Jun 5 - Jun 6
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Pool
Duval Square in Key West
10.0 out of 10, Exceptional, (12)
"Great location and nice accommodations. Very enjoyable trip. Located right by Duvall Loop free trolly so no reason to pay for the old Town Trolly. Only negative is I don’t like having to wash dishes and put away, having to strip beds and do their laundry. This is my vacation so I could do these things at home. Manager helped 2 old people with our luggage because we thought the elevator was out of order. He even took it up the stairs to our bedroom. So nice and helpful!"
Duval Square in Key West
Pool
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
10.0 out of 10, Exceptional, (72)
"This home was wonderful! House had all we needed and was very comfortable. Fully gated yard which was perfect for our dog. It was in such a quiet and peaceful part of town that we sat on the deck and enjoyed the small pool every day. We walked into town each day and we explored all of Old Town from the North end (great marina, restaurants and view) to the South end (great views, restaurants and shopping). Would absolutely recommend this home and would we definitely would rent here next time!"
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
Save an average of 15% on thousands of hotels when you're signed in
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is CA $294
CA $503 total
includes taxes & fees
Jun 4 - Jun 5
Poolside Cottage #411
A heated pool
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
10.0 out of 10, Exceptional, (54)
"From the moment we arrived at our Key West retreat, we were enchanted despite the initial hiccup of discovering that two of the bedrooms were situated on the third floor. Yes, the stairs were a bit of a challenge, but what awaited us inside made it all worthwhile. The accommodation was exceptionally cozy, with a delightful small pool that became our little oasis. Cleanliness and comfort were top-notch, and the location could not have been better, placing us right in the heart of Kew West and...
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w/ Private Pool!
Pool
Great Family Vacation Rental.
10.0 out of 10, Exceptional, (3)
"The townhome was nice and is located in a quaint community. The pool area was beautiful. We found that we needed to Uber into Key West since parking is very limited and we were told the bus service is often not on time."
Great Family Vacation Rental.
TV
SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
10.0 out of 10, Exceptional, (16)
"Everything about this was perfect. Location is great. Having a parking spot right at the rear of unit was a huge plus. Communication with property manager was a breeze (and he even got us in early!) Unit was super clean, updated and well stocked. Having the concierge service was definitely an added plus"
SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
Fridge, microwave, oven, stovetop
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
10.0 out of 10, Exceptional, (31)
"We had an amazing time! The house is within walking distance of everything! Really cool layout, and we all had our own bedroom and bath. The pool is great as well!"
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
TV
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
10.0 out of 10, Exceptional, (21)
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (6)
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
The price is CA $294
CA $503 total
includes taxes & fees
Jun 5 - Jun 6
Poolside Cottage #412
A heated pool
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
10.0 out of 10, Exceptional, (68)
"Beautiful property inside and out. The patio and pool area was perfect for both sun and shade throughout the day. House had all the necessities for cooking and entertaining. We had a blast. Looking forward to our next stay there."
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Outdoor pool, a heated pool
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
10.0 out of 10, Exceptional, (388)
"We loved our stay at Judy’s place. It’s a short drive into downtown key west. We rented a car and took Ubers, which were readily available. The house was exactly as described and so nicely decorated. Had everything you need, including plenty of towels for bath and pool. Pool was very clean and relaxing. The house feels very private with all of the landscaping. Across the street is a great brewery, coffee shop and pizza/Italian restaurant. Judy was so helpful and responsive. Highly recommend to...
Casa Cay West Beautiful Tropical House 3 bedrooms 2 KING suites POOL 2 mi beach
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (190)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
The price is CA $951
CA $2,069 total
includes taxes & fees
May 22 - May 23
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Property grounds
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
9.8 out of 10, Exceptional, (57)
"We had a very positive stay at Tropical Retreat. The property is in a great location and was very comfortable. It was as presented on the website and the property managers were great to work with."
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1/2 Block From Duval St. w/ Pool!
Outdoor dining
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
9.8 out of 10, Exceptional, (59)
"If you like being right downtown in the middle of shops, restaurants and entertainment this place is for you. We parked our car upon arrival and never used it until check out. This is the perfect house for two or maybe three people. We really had a great time."
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w/ Outdoor Area Steps to Duval!
Smart TV
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
9.8 out of 10, Exceptional, (73)
"Great place!! Very convenient You get what you see Quiet in the gates but duval street 100 feet"
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (203)
"Fantastic property and location, our 2nd time there. Melanie, the host, is super responsive. I would highly recommend."
The price is CA $476
CA $601 total
includes taxes & fees
Jun 16 - Jun 17
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
9.8 out of 10, Exceptional, (153)
"Loved this home! (even asked to buy it) plenty of room comfortable beds, great pool and grounds. I have stayed at dozens of properties in Key West and this is hands down my favorite. Location doesn't get much better as well. Overall fantastic"
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
Pool
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
9.6 out of 10, Exceptional, (184)
"The stay was excellent, a beautiful home with lovely touches to make you feel comfortable. Overall I gave the highest rating, but the TV didn’t work. The manager was attentive but still took a few days to resolve the issue. Also, pool guy arrived unannounced to service the pool, I would have preferred notice. As I said it was overall perfect in terms of location, cleanliness and charm, would recommend it!"
MANGO MARGARITA~ 2 bedroom/2.5 bath, heated private pool, and close to Duval!
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.6 out of 10, Exceptional, (90)
"House was exactly as stated. We enjoyed it there. Close enough to downtown to enjoy it. Nice touch having the bikes there to use! Condo pool was great too. We enjoyed the amenities! Would stay again if we came back to the area!"
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Don't see what you're looking for?
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 property types in Dredgers Key

Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is CA $294
CA $503 total
includes taxes & fees
Jun 4 - Jun 5
Poolside Cottage #411
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (190)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
The price is CA $951
CA $2,069 total
includes taxes & fees
May 22 - May 23
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is CA $135
CA $326 total
includes taxes & fees
May 20 - May 21
Steps from Duval, Pool & Bikes $129-$299 Night!
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.

Dredgers Key Vacation Homes information

Number of reviews
1,016
Accommodation
533 Vacation Homes
Lowest Price
CA $294
Highest Price
CA $951

Recent Reviews in Dredgers Key
Expedia verified reviews