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BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal

Waterfront holiday home with private pool and kitchen

Photo gallery for BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal

Pool
Master bedroom.
The lounge
Pool
Outdoor dining

Reviews

9.4 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6176.5 sq m

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Fireplace

Explore the area

View map
Key West, FL
  • Place, Smathers Beach
    ‪4 min drive‬
  • Place, Duval Street
    ‪10 min drive‬
  • Place, Southernmost Point
    ‪10 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪5 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single Beds and 1 Crib

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Separate dining area
Outdoor play area
Garden

About this property

BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal

LOCATION LOCATION! Located on the only canal in Key West, with a protected bird sanctuary across the canal. A short Uber ride to Duval Street to all of Key West's fun filled amenities. On the same street as Jimmy Buffet's former home in New Town. A short walk to the ocean.

BOAT LOVERS! Five minutes to open ocean. Keep your boat in the canal right at your back door.

KAYAK LOVERS! Slip the two sea going kayaks into the water and explore the mangrove trails and Salt Ponds right across the canal.

ANGLERS! Fish directly off the stone deck out back and catch anything from snapper to grouper. Throw them on the grill and have dinner by the water.

Serenity and privacy can be yours as you relax on the patio by the large free form pool, right across from a protected bird sanctuary with gorgeous unencumbered views of the sunrise and sunset over the mangroves. Ten minutes away from the zany fun of Duval Street when you are ready to party. Two bikes (Cruisers) available to explore the hidden corners of the island.

A beautifully landscaped, family-owned home on Key West's only canal, Dragonfly gives you the feeling of visiting an old friend instead of a sterile rental unit. This 1950's retro-chic house is furnished with an eclectic combination of custom furniture, family antiques and wicker in an exclusive area of Key West not usually on the rental market. This property includes all the amenities of your own home. You will enjoy two newly remodeled baths, a fully functional kitchen, linens, big screen SMART TV (Prime, Netflix, MAX, HULU, etc), high speed internet, washer/dryer, air conditioning and outdoor grill. The backyard has plenty of seating by the luxurious private pool on the water. Large private driveway for parking multiple vehicles and a boat/trailer.

Bedding configurations: 3 BR 2 BA. Two king size beds (one of which can be separated into two twins) along with a twin bed with trundle. Additionally two pillowtop King and Queen blow up mattresses for your convenience. 1900 square feet. Large wrap around yard.

If you are looking for that anonymous condo feel this is not the place to go, but if you want a home away from home that is charming and relaxing Dragonfly is for you.

Due to local law this property can only be rented by the month. Full months only. No pets allowed.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 11:00 AM
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Children

Children allowed: ages 3–17
WARNING: sea wall is a 6’ drop into the water.
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Events

No events allowed
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Pets

No pets allowed
Care dogs allowed
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Smoking

Smoking is not permitted
Rent: 1/2 up front, non refundable if no new renter is located. 1/2 at 60 days out, non refundable if no new renter located.
Due to local law this property can only be rented by the month. FULL MONTHS ONLY (not half of one month and half of the next one.)

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock

About the area

Key West

Located on the waterfront, this holiday home is in New Town, a neighbourhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Smathers Beach. Travelling with kids? Consider Key West Tropical Forest and Botanical Garden and Key West Butterfly and Nature Conservatory. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with horse riding and ecotours.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Smathers Beach - 4 min drive - 2.4 km
  • Key West Golf Club - 5 min drive - 2.1 km
  • Duval Street - 10 min drive - 5.0 km
  • Southernmost Point - 10 min drive - 5.0 km
  • South Beach - 10 min drive - 5.0 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 4 min drive

Restaurants

  • ‪McDonald's - ‬18 min walk
  • ‪Toasted Coconut - ‬16 min walk
  • ‪Outback Steakhouse - ‬3 min drive
  • ‪Starbucks - ‬16 min walk
  • ‪Wendy's - ‬3 min drive

Frequently asked questions

Does BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal?

As of 11 Nov 2025, prices found for a 1-night stay for 2 adults at BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal on 30 Nov 2025 start from AU$946.85, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal pet-friendly?

No, pets are not allowed at this property.

What time is check-in at BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal?

Check-in begins at 4:00 PM.

What time is check-out at BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal?

Checkout is at 11:00 AM.

Where is BARGAIN FOR DECEMBER 2025! 1/3 OFF REGULAR PRICE! Private Home/Pool/on canal located?

This family-friendly Key West holiday home is located on the waterfront, within 1 mi (2 km) of Key West Tropical Forest and Botanical Garden and Regal Key West. Duval Street and Smathers Beach are also within 3 miles (5 km).

Reviews

9.4

Exceptional

9.0/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.2/10

Location

9.2/10

Listing accuracy
Rating 10 - Excellent. 15 out of 20 reviews
Rating 8 - Good. 4 out of 20 reviews
Rating 6 - Okay. 1 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

Reviews

10/10 Excellent

Patti S., Pennsylvania

Liked: Cleanliness, check-in, communication, location, listing accuracy

Precious jewel in Paradise

We absolutely loved this property. The outside covered patio area is wonderful to eat meals or just relax. The pool is just perfect to float around and cool off when needed. We biked and kayaked almost everyday. Had a vip visitor to the dock one day, a beautiful manatee. Each room has its own AC units so everyone can have it just as they like it. The main area has a lot of seating/gathering areas for the guests. The hosts were incredible with their communication and quick response if I had any questions. The house has everything you need. Just bring your clothes and bathing suit to enjoy your time in beautiful Key West.
Stayed 31 nights in Dec 2022

8/10 Good

Kathy G.

Liked: Check-in, communication, location

Fun

Fun location, fishing off deck not very good, kayak access for getting in water poor
Stayed 30 nights in Mar 2025

8/10 Good

Jaime P.

Liked: Cleanliness, check-in, communication, listing accuracy

Good for boaters

Older 70’s style home on canal with pool. I enjoyed the house but not being so far from Old Town (25 mins bike). I feel property would be best enjoyed by someone who has a boat and also a car. The pool is really nice, but was too chilly to enjoy this January. The kayaks are heavy and must be maneuvered over/back up a 6’ seawall while balancing on a small floating dock. I was unable to use them but was delighted with three manatee sightings from the deck. The home was comfortable and relaxing just not well suited to my situation.
Stayed 28 nights in Dec 2023

10/10 Excellent

Christine W., Petoskey, Michigan

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoyed our stay

Quiet neighborhood. We didn't mind the distance to downtown. Pool is very nice. Plenty of room inside. Outdoor living area is roomy and relaxing. Enjoyable watching the boaters an dhayakers go by in the canal. Owner was attentive and easy to work with. We would stay again!
Stayed 30 nights in Mar 2023

10/10 Excellent

john K., Excelsior Minnesota

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoy our time very much thanks to our host

Great quiet neighborhood and home with lots of room. Enjoyed patio area very much and did get to see manatee.!
Stayed 30 nights in Jan 2023

10/10 Excellent

Patty W., Hapeville, Ga USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

House was wonderful, air conditioners in each bedroom allowed individuals to control their own air. Property owner very involved and concerned about our stay, when we had a pipe leaking stayed in contact with us. They were a little slow in getting it fixed, but otherwise everything was great.
Stayed 31 nights in Dec 2021

8/10 Good

Joann G.

Great House

The house is perfect. The pool & canal were great to have. We rented a boat & fished everyday. Close to downtown when you need a little shopping & restaurants, The only reason I didn’t give it a 5 star was because of bad communication w/ owner. Every rental gets 1st chance to rebook for next year same time period. This did not happen. They let someone else rent the house for next year. Even if they are new at this, they should have known how things work
Stayed 31 nights in Feb 2019

10/10 Excellent

Kathy J., Halfmoon, New York

Enjoyed our stay!

The spacious house is conveniently located in a quiet residential neighborhood. It is just a short drive to everything Key West has to offer . . . great fishing, restaurants, entertainment and beautiful sunsets. We enjoyed the private outdoor space, updated bathrooms and comfortable beds. We are looking forward to our next visit.
Stayed 30 nights in Jan 2019

10/10 Excellent

Donna P., Denver Colorado

Great find!!!

The living area is spacious and the home had everything we needed. Owners have done a nice job rehabbing the home while maintaining its retro style. The canal is great for kayaking and we kept our boat on the sea wall. Thanks for a great month!
Stayed 31 nights in Dec 2018

10/10 Excellent

Lucielle M.

Awesome location- easy boating access to both Gulf and Atlantic side! Awesome house & pool!

We really enjoyed the vintage features of the home and appreciated the beautifully updated bathrooms. The pool was the perfect hang out spot after a day of boating. We loved being right there in KW without having to be right in the middle of the touristy part. Downtown KW is a mere 3 miles away and an easy bike ride away! Convenient canal location allowed access to both the Gulf and Atlantic. We loved having access to the kayaks to discover the salt ponds and visit a very friendly manatee we named “Manny”. The neighbors are the mangroves and the variety of birds which created the perfect tranquil and private outdoor vista to enjoy early morning coffee. We really loved being here and we're worried that it’s only a matter of time before others will begin to discover the absolutely best spot in KW to vacation!
Stayed 30 nights in Jun 2018

10/10 Excellent

Joseph B.

If your a boater and love key west then you will love this home.

The house is great but what makes this place special is the outside pool area and the boating access. Your just a short canal trip to anywhere in the keys your boat can take you . The house gives you easy access to the great places in key west but allows you to escape the Duvall street crowds once you have enjoyed that yourself .
Stayed 29 nights in Jun 2017

8/10 Good

Tim C.

Great water access for kayaking and boating!

This house was exactly what we were hoping for. We brought our boat and enjoyed fishing and diving for lobster many days. The pool is refreshing after a hot day of boating or kayaking. Quiet neighborhood but close enough to bike to Old Town. Needs more outdoor furniture for outside dining however. Great time overall!
Stayed 30 nights in Mar 2017

6/10 Okay

Nancy H.

my 2 cents

The home has much character kind of like my house so I felt at home. Easy to get out to Atlantic and Gulf unfortunetly the weather was not cooperating for us. I especially like the pool and all the gardens. If I was staying there again I most certainly want a freezer for ice. and most of all calm seas! I Most certainly recommend this home to my friends. Not into partying toooooo much so I stayed away from Duval and enjoyed the rest of the city. Love the food at El siboney Cuban food! the wines bring your own!
Stayed 30 nights in Jul 2016
This review was submitted before 2018 and has not been verified.

10/10 Excellent

TOM G.

This is a state of mind, not a vacation rental.

This is an authentic 60's era architecture house on the waterway and salt marsh. Very well-maintained and charming. The back patio is covered and a wonderful place to spend the day reading, and watching the boats, kayaks, paddle boarders, manatees and tarpon roll by. We sat out there during a fierce squall and stayed dry. The pool is wonderful, there are always areas in shade and sun to move around in. Good kayaks and Bikes at your disposal. Wifi, big screen TV, excellent washer/dryer, great vintage full kitchen, neat sunken living room, comfortable beds with good mattresses, kickass air conditioning, very private, great jogging neighborhood,... A week here and your mind will be in a better place!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Test T.

Everyday I stayed just got better and better

A serene and wonderful spot. The outside view over the mangrove is amazing. Kayaking in the back each morning was fantastic - with the occasional manatees swimming by. The pool is made for relaxing and watching sunsets. The decor is primarily 50s and it's a normal home with everything you need. If that's not your thing or you want something fancy however, this may not be the place for you. We loved it.
Stayed 30 nights in Mar 2016
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Chris T.

Perfect place to get away from it all!

First let me say that at first I was a little concerned about the location for this property as it looks on the map to be a long way away from Duval and some of the other hotspots of Key West, but I found after arriving that this really enhanced my stay. Being away from all of the night-time craziness allowed me and my family to have a much more enjoyable and relaxing trip. A few gems from the trip that we haven't been able to get at other places in Key West: 1) Taking out the sea kayaks to explore the mangrove swamp behind the house; 2) Set up the ping pong table and doing my best Forrest Gump impersonation; 3) Petting the manatees that came right up to the seawall behind the house (I'm sure someone will scold me for doing this, but c'est la vie); 4) Cooking up some fresh lobsters and grouper on the grill; 5) Jumping in the canal behind the house after a day at Smather's Beach. This is a great property that really makes you feel at home. I can't wait to go back again!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Doug H.

Hidden Treasure!

First of all, the photos on Homeaway don't do this home any justice. The home is absolutely beautiful and is located in "new town" which is away from all the noise and touristy stuff in "old town" near Duval St. My wife an I go to Key West 2 - 3 times per year and only stay at this property. The home is really set up for enjoying being outside. The house site on the only canal in Key West and it was fun to sit in the pool and watch boats, kayakers and paddleboarders roll by. One boat even threw us a couple of fresh snapper they just caught! The mangrove forest (an attraction that people pay to kayak through) is right on the other side of the canal and there are two kayaks at the house...you can just go at your liesure. There is also a ping-pong table, two beach cruiser bikes, a grill, lounge chairs and a huge covered area outside in case of rain or if you just want to get out of the sun for a bit! Being here gives you a true sense of what's like to actually live in the Key West paradise.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Howard N.

The best way to melt into the Keys

I love KW and everything about it. I've stayed all over Old Town and walked the island from place to place. A friend sent me the link to this site when I needed a longer stay option. I was very surprised how much more space you have in New Town. This home is on a large canal. What makes it so great, is there aren't homes across the water. Just trees and sky. There is also a pool. Its shallow and ideal for sitting and half standing. My wife and I like to grill out, listen to music, and lounge in the pool day and night. The best part is, there's nobody to see what you are or aren't wearing. This was a hit with my wife. When we did manage to get dressed and leave, Duvall is just a 10 5 min taxi ride away. The airport is 3 mins. I'll be back!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Heather D.

Fantastic stay. Totally serene.

A wonderfully serene and beautiful spot. I rarely left the back deck. Gorgeous sunrises and sunsets almost everyday I was there. Quiet and peaceful with beautiful unencumbered views over the mangrove. I'd spend my mornings on the kayak paddling into the tunnels across from the Sea wall or reading by the pool under the palm tree it's built around. The home is very 1950s style and nothing fancy inside- but everything you need. It has a very homey feel - not the plastic or generic feel of a condo or hotel room. I like that, but if you are looking for that condo feel or something real fancy - this is not the place to go. But if you want a home away from home that's totally relaxing I'd highly recommend it.

10/10 Excellent

john p.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 30 nights in Mar 2024

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