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South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub

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South St. Cottage
South St. Cottage
South St. Cottage
South St. Cottage
South St. Cottage

Reviews

9.8 out of 10, Loved by Guests
Top 10% based on
2 bedrooms2 bathroomsSleeps 41000 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 2

1 King Bed

Main Bedroom

1 King Bed

2 bathrooms

Bath 2

Main Bath Ensuite

Spaces

Kitchen
Garden

About this property

South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub

28 DAY MINIMUM RENTAL

This bright and sunny cottage is situated on a quiet residential street. Guests can walk to the nearby beaches, White Street shops, and enjoy the sunny pool, hot tub and patio space.

A large open kitchen, skylights, light tile floors and french doors leading from the living room & both the bedrooms to the pool area create a real indoor/outdoor living experience. The living room is spacious & comfortable with bright tropical colors with a small lounging corner where you can relax in the overstuffed chaise, read a good book, take a nap, all while gazing out to the pool and patio. Several new upgrades have been added by the owners including a new ductless air conditioner to cool or heat the living area.

The master bedroom sits to the rear of the property with french doors to a private patio space complete with the new 6-person hot tub. It's your own outdoor spa! The second bedroom is on the front of the house adjacent to the living room with French doors leading out to the pool. Bedding: 2 kings, 1 sleeper sofa.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

We should mention

A car is recommended for transport to and from this property

About the area

Key West

Located by the sea, this holiday home is in Key West Historic District, 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 Fort Zachary Taylor Historic State Park and Florida Keys Beaches. Key West Butterfly and Nature Conservatory and MLK Community Pool & Community Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Key West, FL

What's nearby

  • Clarence S. Higgs Memorial Beach Park - 9 min walk - 0.8 km
  • Smathers Beach - 16 min walk - 1.4 km
  • Duval Street - 16 min walk - 1.4 km
  • South Beach - 17 min walk - 1.4 km
  • Southernmost Point - 18 min walk - 1.6 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 6 min drive

Restaurants

  • ‪Circle K - ‬12 min walk
  • ‪Dions Truman & White - ‬9 min walk
  • ‪Morrison's Market - ‬11 min walk
  • ‪Sandy's Café - ‬9 min walk
  • ‪Popeyes Louisiana Kitchen - ‬15 min walk

Frequently asked questions

Does South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub?

As of 5 Mar, 2026, prices found for a 1-night stay for 2 adults at South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub on 2 Jun, 2026 start from S$269, 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 South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub?

Check-in begins at 4:00 PM.

What time is check-out at South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub?

Checkout is at 10:00 AM.

Where is South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub located?

Located in Key West Historic District, this holiday home is within a 15-minute walk of Bayview Park and Florida Keys Beaches. Duval Street and South Beach are also within 1 mile (2 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 27 out of 30 reviews
Rating 8 - Good. 2 out of 30 reviews
Rating 6 - Okay. 1 out of 30 reviews
Rating 4 - Poor. 0 out of 30 reviews
Rating 2 - Terrible. 0 out of 30 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Amy H.

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

The spot

Our new home away from home! Everything was above and beyond exceptional! Cant wait to go back! Had everything we needed- fully stocked! Super clean. Private. Comfortable. 5 stars all around. Thank yall
Stayed 30 nights in Jan 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Bruce D.

Fantastic!

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: South St Cottage was one of our best rentals ever, and we rent a lot! It was by far the best-stocked home as far as kitchenware, supplies, etc. They thought of EVERYTHING, and it was all very nice quality, not just cheap "rental" items. We were so impressed. The pool is wonderful, the beds were comfortable, plenty of space for parking, a great location...everything we needed. And a fabulous new waterfall rain shower in the primary bath! Extensive artwork collection, too. Again, very nice things as if it were the owner's home and not just a rental. The only cons were that the floors were rather dirty upon arrival, almost as if the cleaning crew had missed them somehow. Also, the deck by the pool had several sections that are a little rotted out and for children or elderly folks could pose a hazard to walk on. We noted the owners have a building permit posted out front where it appears they intend to repair the decking. We discovered, entirely by chance, a drawer at one end of the kitchen/dining table that has a cornucopia of pamphlets, coupons, and other great info about Key West attractions and restaurants—renters should be notified about this treasure so they can benefit from all the good info. So, all in all, would absolutely recommend this cottage to anyone wanting a great, quiet, and well-located stay in KW!
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

A guest from Sarasota, FL

South Street Cottage Monthly Stay

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The South Street Cottage was in an ideal location. We had ideal room for both of us to work remotely. The Cottage is furnished with everything we needed for our month long stay.
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Audrey W., N. Florida, USA

Perfect Private Oasis

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We thoroughly enjoyed our stay in this home! It’s located in a quiet, well-kept neighborhood with easy parking out front and quick biking access to everything. The home was larger than we expected, was well stocked, and very clean. Even if you never leave the front yard tropical pool oasis, you will not regret this stay. Most definitely would not hesitate to stay again!
This review is from a guest who booked and stayed through a partner site and can't be verified.

8/10 Good

A guest from Boothwyn, PA H.

Enjoyable

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Charming home in a quiet neighborhood- worth the visit. Thanks Shad and Jann for everything
This review is from a guest who booked and stayed through a partner site and can't be verified.

6/10 Okay

lynn g.

Great Pool But Dirty and Falling Apart!

Rating Details: The property manager was very unhelpful. The vacation rental was very dirty. I was happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The outdoor space and pool is fabulous. The weekly pool man did a wonderful job.....But, the house was dirty (moldings hadn't been washed or dusted for at least a year, some dishes had mold on them, and the toilet was barely wiped clean to name just a few of the cleaning issues) and much needed fixing (the dishwasher was falling out of the cabinet and flooded the entire kitchen floor the first time we used it ~ the towels were filthy when I wiped all that water off the floor/ didn't plan on washing floors on my vacation!), the air conditioner did not work in the second bedroom and was probably the reason there was black mold behind the bed and nightstand, the front gate lock wasn't keeping anyone out because it was falling off, the towel bar on the sliding glass shower door fell off in my hands, and there was a large hole in the living room wall from someone pushing a couch too hard into the wall.) Overall, it seems as though nothing has been done to this house in years! When I called Rent Key West the first day and reported all of this they wanted to send people out to address my long list, but I was on vacation and didn't want to entertain a bevy of work people coming and going. They did quickly send someone to fix the dishwasher and replace the gas tank for the grill (which no longer lit automatically. We had to go buy a lighter to get it started). Lastly, we stopped in to see the rental agent and when her bulldog came from out of nowhere and attacked our 12 lb dog, I fell on my back during the rukus. A decent, caring person would have called the next day to see how I was. Nope, never heard from her. Before her dog caming running out she was blaming the management company for the poor condition of the house, isn't that them?? This rental agency has lost our business. We have rented a far more expensive house for three months in Key West for next winter, but not this house or with this rental agency.
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Jim S., Washington DC

January in Paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We really enjoyed our stay at South Street Cottage. It was in a quiet neighborhood, but close enough to walk or bike to the beach and wonderful restaurants.
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Jim and Diane M.

Home Sweet Home

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We recently completed our third year of renting South Street Cottage and we already have our reservations in for next year! Needless to say we love the house and the location. It's the perfect size and has the open floor plan that we love, with french doors that allow you to feel a part of that gorgeous KW weather. One month is never enough!!
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Sherri W., Waynesboro

South st cottage

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had an absolutely wonderful time! We loved it here and being secluded once inside the gates was wonderful! We have already saved this rental for next year!
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Holly A.

Great Rental Property

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is our 3rd year staying at South St. Cottage. Great location and property. This year the tile floor and refrigerator were new. The kitchen is very well stocked, plenty of closet & storage space, 2 bedroom & 2 bath are great for 2 couples. The pool & outside area is the best part of the rental! A must when staying in Aug. The management is awesome. We had an issue with the washer that was fixed right away. There was a power outage on the island and the outside lights and pool were off schedule. They came out right away and reset them. Highly recommend this property.
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

richard s.

Fourth time for a two stay.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: When we arrived at RENTKEYWEST to check in, Joyce said "welcome home". And, we did feel like we were coming home. South Street is the perfect property to stay in while in Key West. It is a large two bedroom with a lot of living area. It is always in tip top shape. The owners and RENTKEYWEST are constantly addressing maintenance and updating and it shows. Park your car , enter the private retreat, unpack you bags, and you are home. Our favorite spot is the large front porch overlooking a beautiful pool with lush green landscaping. From the pool to the hot tub or relaxing with a steak on the grille, you will love this oasis.
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Laura M.

Always Sunny at South Street Cottage

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My husband an I thoroughly enjoyed our time at SSC - lovely neighborhood and the cottage is super!
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Kevin B.

January 2018 After Irma Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: After hearing about Irma we were concerned about what to expect b I get that we are very familiar with recent hurricanes. The drive from Islamorada South was through the worst hit areas. Trash was piled up on the side of the mHWu 1 almost the entire distance to Key West.Wow, we arrive in Key West and there was virtually now impact visible Naldo on the return trip ALL the trash on the other keys have been removed. I have to give Monroe County and the State of Florida a big Kudos for the enormous job they had getting the Keys in such great shape so quickly.Our stay also benefited from lighter than normal hotel stays , so parking was never a problem the entire month. Never need a reservation fo a meal and never had a wait line. So to be honest it was our best vacation ever and having been to Key West and Islamorada before this was very unusual for January and the traffic flow between the Keys was a breeze.The property was awesome, location is perfect. 10 minute walk to a beautiful Whites Pier. Restaurants everywhere and a grocery nearby although expensive it’s very convenient. Publix is 10 minutes away, but so is everything elseWe had our own car, but we used Uber a few times, average wait 1 minute so be ready.Best pizza delivery was the top rated on Google and it was a flat $20 best deal on the island. Sint is a Burrito, taco and craft beach place, again sub $20 food but the best I have had anywhere in California or Mexico.Ladeta show must do, great entertainment. We did a play is was a fun night.Breakfast Bannana Cafe roof top, and the pastry shop next door had the best breakfasts. Blue Heaven was OK, maybe over hyped. Schooner Bar best Wings , to be honest there are tons of great food establishments.Great festivals, and something to do every day. Very safe neighborhood and yes you have Iguanas, one big one. Dogs love the yard great privacy and landscaping. Kitchen has all the
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Jim and Diane M.

Best Ever!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We rented South Street Cottage in Key West for November and December was the best vacation we have ever experienced! Perfect weather...perfect house...perfect neighborhood. This was our third year renting from Rent Key West Vacations, they did an excellent job as always, and our second year renting this house. We already have it reserved for next year...that says it all!
This review was submitted before 2018 and can't be verified.

10/10 Excellent

richard s.

Our third year in a row!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We have only been back at home for two days and we are missing our second home in Key West. We completed our two month stay for the third year. South Street cottage is the perfect place to be. It is an ideal two bedroom house with a great porch overlooking a beautiful pool with luscious landscaping. A very private oasis in a quiet residential neighborhood. The owners have gone great lengths to make it very comfortable and up to date with a new and fresh interior. All the amenities are first class. You can also expect First Class service from the entire staff at Rent Key West. Rent Key West leaves all the i's dotted and the t's crossed. They are the premier agency in Key West.
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Laura M.

South Street oasis

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Out stay was wonderful - perfect quiet location - but close enough to all the key west attractions to walk if you want to.
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Ed H.

Two Months In Paradise!

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Celebrating my wife's retirement, we decided to go as far south as we could while still be able to take our 3 kitties with us. We couldn't leave them home for two months. Anyway, we enjoyed our stay in this quiet neighborhood. Most photos aren't necessarily a true representation of the property. In this case it was. Very nice pool area located in front. Spa on rear deck. Beds and furniture were very comfortable and kitchen had all you needed. It's not a short walk to Duval but you have a couple, few restaurants within walking distance. Fausto's grocery is close and offers most everything. Next time in the Keys we will strongly consider this property again.??
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Holly A.

Great house in paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is our 2nd year staying at South St. Cottage. House is spacious - plenty of light from sky lights, king beds are comfortable, kitchen is fully stocked, plenty of closet space, awesome pool and outdoor space. Great location on a quiet street with parking right out front.
This review was submitted before 2018 and can't be verified.

10/10 Excellent

September 2016 South Street Wrap Up

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: we enjoyed our stay at the SS Cottage very much. It had all the right household goods and comfortable was luxurious & oh so very comfortable, a delightful place to come home to after a "hard day at play" in Key West!
This review was submitted before 2018 and can't be verified.

10/10 Excellent

richard s.

Our second home.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The south street cottage is perfect in every way. This is the second year we have stayed there. We extended our stay to two months this year and it couldn"t have been more pleasant. We enjoy the privacy of the compound with the beautiful pool in a tropical oasis. The house is only a two bedroom but it is very spacious and decorated beautifully. The design has a great flow with a single level. The owners should be very proud of their cottage and I can't say enough great things about Rent Key West. The rental company will cater to your every need. I rate this property A++++
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Lis G.

South Street

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautifull spacious house with a well equipped kitchen and lovely yard. New air conditioning was quiet and efficient. The house was charming with a split bedroom configuration ideal for privacy.
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Laura M.

South street cottage

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our stay at South Street cottage was wonderful. The cottage is well stocked and great location in quiet neighborhood but close to the beach and several good restaurants. Lovely!
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Jim and Diane M.

South Street Cottage is my #1 Pick!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Open the gate and you've entered a private world of lush landscaping, a deep water pool, lots of lounge space, and a private hot tub for the master suite. Entire cottage is just as beautiful as shown in the pictures. Layout of house is great for entertaining and privacy. Zoned AC makes it particularly comfortable for all. Quiet neighborhood that's centrally located is perfect for bike riding. Our pets were in heaven, especially our rottie, who loved the freedom of the securely fenced in yard. This is our second year with Rent Key West Vacations, and we would not use anyone else!
This review was submitted before 2018 and can't be verified.

10/10 Excellent

Holly A.

Great Rental House

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great private, fulled fenced and gated house on a quiet street! Pool is awesome - large and deep and great for cooling off on a hot summer day. Very bright inside with sky lights, large, well laid out floorplan, plenty of dishes, utensils, pots & pans, great storage and closet space. Hot tub with a sitting area in back is a nice feature in the cooler months. Huge flat screen TV, plenty of seating for guests, king beds in both rooms were very comfortable, large dining table, outdoor area around the pool is great with lots of chairs and loungers. Property was clean - a couple of broken tiles in kitchen, worn vanity in master bath, a few stains on throw rugs - but nothing that would deter us from renting again. Parking spot right out front, close to beach and dog park and City Marina. Bike ride to everything. Management company was great to work with! Overall very happy with this rental and would rent again!
This review was submitted before 2018 and can't be verified.

8/10 Good

Stephen U.

Key West Vacation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our rental experience was great. The house was as advertised and met all of our needs and expectations.

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