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

As of 5 November 2026, prices found for a 1-night stay for 2 adults at South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub on 1 December 2026 start from NZ$22,564, 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.

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

Q: 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.

Q: Is South Street Cottage: Bright & Sunny with Pool, Patio & Hot Tub pet-friendly?

Yes, pets are allowed at this property.

Q: 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).

Verified review

10/10 Excellent

Amy H.

15 February 2024

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

From a partner site

10/10 Excellent

Bruce D.

3 June 2022

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!

Response from VrboOwner on 16 June 2022

Thank you for your review. We are so glad that you enjoyed the cottage and its location. We greatly appreciate your feedback and have addressed those issues you mentioned. Thanks again for your review and recommending South Street Cottage to anyone wanting a great, quiet and well-located stay in Key West!

From a partner site

10/10 Excellent

A guest from Sarasota, FL

3 August 2021

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.

From a partner site

10/10 Excellent

Audrey W.

3 July 2021

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!

From a partner site

8/10 Good

A guest from Boothwyn, PA H.

1 June 2021

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

From a partner site

6/10 Okay

lynn g.

25 March 2021

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.

From a partner site

10/10 Excellent

Jim S.

22 February 2019

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.

From a partner site

10/10 Excellent

Jim and Diane M.

10 January 2019

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!!

From a partner site

10/10 Excellent

Sherri W.

1 November 2018

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!

From a partner site

10/10 Excellent

Holly A.

30 August 2018

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.

From a partner site

10/10 Excellent

richard s.

31 July 2018

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.

From a partner site

10/10 Excellent

Laura M.

6 March 2018

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!

From a partner site

10/10 Excellent

Kevin B.

4 February 2018

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

From a partner site

10/10 Excellent

Jim and Diane M.

21 January 2018

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!

Archival

10/10 Excellent

richard s.

23 July 2017

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.

Response from VrboOwner on 20 May 2022

Thank you for the wonderful review! We look forward to seeing you every year. South Street Cottage is one of our most popular rentals and you described it perfectly in your review. Thanks again!

Archival

10/10 Excellent

Laura M.

17 March 2017

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.

Archival

10/10 Excellent

Ed H.

1 December 2016

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.??

Archival

10/10 Excellent

Holly A.

1 September 2016

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.

Archival

10/10 Excellent

1 September 2016

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!

Archival

10/10 Excellent

richard s.

10 August 2016

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++++

Response from VrboOwner on 26 May 2022

Thank you for your wonderful review! We truly appreciate your business. We are very happy to hear that our staff and South Street Cottage met your needs and expectations. We look forward to you staying with us again next year!

Archival

10/10 Excellent

Lis G.

6 May 2016

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.

Archival

10/10 Excellent

Laura M.

1 March 2016

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!

Archival

10/10 Excellent

Jim and Diane M.

21 December 2015

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!

Archival

10/10 Excellent

Holly A.

1 September 2015

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!

Archival

8/10 Good

Stephen U.

17 July 2015

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.

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

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

Reviews

Highlights

Popular amenities

Explore the area

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 2

Main Bedroom

2 bathrooms

Bath 2

Main Bath Ensuite

Spaces

Add dates for prices

Similar properties

Private Paradise with Heated Waterfall Pool

About the area

Key West

What's nearby

Getting around

Restaurants

Frequently asked questions

Reviews

Exceptional

10/10

10/10

10/10

10/10

10/10

Reviews

10/10 Excellent

Amy H.

The spot

10/10 Excellent

Bruce D.

Fantastic!

10/10 Excellent

A guest from Sarasota, FL

South Street Cottage Monthly Stay

10/10 Excellent

Audrey W.

Perfect Private Oasis

8/10 Good

A guest from Boothwyn, PA H.

Enjoyable

6/10 Okay

lynn g.

Great Pool But Dirty and Falling Apart!

10/10 Excellent

Jim S.

January in Paradise

10/10 Excellent

Jim and Diane M.

Home Sweet Home

10/10 Excellent

Sherri W.

South st cottage

10/10 Excellent

Holly A.

Great Rental Property

10/10 Excellent

richard s.

Fourth time for a two stay.

10/10 Excellent

Laura M.

Always Sunny at South Street Cottage

10/10 Excellent

Kevin B.

January 2018 After Irma Stay

10/10 Excellent

Jim and Diane M.

Best Ever!

10/10 Excellent

richard s.

Our third year in a row!

10/10 Excellent

Laura M.

South Street oasis

10/10 Excellent