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Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven

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Step into your private retreat—this heated pool is the heart of the home, framed by tropical landscape and Florida sunshine.
An aerial of the property—private, peaceful, and beautifully positioned on northern Siesta Key.
Lounge in total privacy spending the day swimming, sunbathing, or relaxing poolside—this secluded backyard was made for island living.
Resort-style relaxation with a blend of comfort and luxury turns your vacation into a five-star experience—without ever leaving home.
Create unforgettable nights with family and friends—pizza and alfresco dining all in your own backyard.

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • Discover nearby landmarks
    Walk to Shell Beach
3 bedrooms2+ bathroomsSleeps 8

Popular amenities

  • Private pool
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Sarasota, FL
  • Place, Shell Beach
    ‪2 min walk‬
  • Place, Irma Beach
    ‪19 min walk‬
  • Place, Siesta Key Beach
    ‪6 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪22 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed

Common Space

1 Double Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Half Bathroom 3

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Dining area

About this property

Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven

🌴 Hemingway House | Screened Lanai + Heated Pool

💖 Why You'll Love This Home
This thoughtfully updated island retreat blends laid-back coastal charm with stylish indoor-outdoor living. Enjoy coffee in the screened lanai, pizza nights by the wood-burning oven, and breezy evenings around the private heated pool—all just 2.1 miles from Beach Access 5 and a short drive to Siesta Key Beach.

👨‍👩‍👧 Perfect For
Families or small groups who want a quiet, design-forward escape with private amenities and fast access to Siesta Key's best beaches.

🎞️ Imagine This
You start the morning with a cup of fresh coffee from the built-in GE Café Keurig, stepping into the screened lanai as soft island breezes drift through the palms. After sun-soaked hours at Siesta Key Beach, you cool off in the private heated pool, rinse off in the spa-style outdoor shower, and prep hand-tossed pizzas in the Mediterranean wood-burning oven. As stars begin to glow overhead, you dine alfresco under string lights, then wind down indoors with plush linens and cozy spaces made for total relaxation.

🛌 Where You'll Sleep
• Bedroom 1: King Bed, Ensuite Bath, Second Floor, TV
• Bedroom 2: Queen Bed, Shared Bath, Second Floor, TV
• Bedroom 3: Full Bed, Shared Bath, Second Floor, TV
• Living Room: Sleeper Sofa – Shared Bath Access

📍 Explore the Area
• 2.1 Miles to Beach Access 5 – A Local Favorite for Shelling and Sunrise Walks
• 3.0 Miles to Siesta Key Main Beach – Iconic White Sand and Family-Friendly Vibes
• 3.2 Miles to Siesta Key Village – Shops, Restaurants, and Open-Air Cafés
• 0.5 Miles to Gulf Gate Dining District – International Cuisine and Local Eateries
• 1.6 Miles to Crescent Beach – Quieter Sands and a Relaxed Coastal Feel
• Located on the Peaceful North End of Siesta Key – Ideal for Tranquil Mornings and Easy Exploration

⌛ Don't Wait
This home books quickly. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection—so you arrive at a home that feels fresh, spotless, and ready for your vacation.

📌 Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high-speed WiFi is included. This home is registered with the City of Sarasota (VR22-00099). Per city code, rentals require a 7-night minimum and a maximum of 8 guests. All bedrooms are located on the second floor. If stairs or mobility concerns apply, contact us directly for personalized recommendations.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 26
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

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 9686720
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, a first aid kit and a deadlock

About the area

Siesta Key

Located near the beach, this holiday home is in Bay Isle, a neighbourhood in Siesta Key. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Looking to enjoy an event or a game while in town? See what's going on at Stardust Event Center, or consider a night out at Tarpon Bay Grill and Tiki Bar. Jet skiing, kayaking and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby.
View more Holiday homes in Siesta KeyOpens in a new window
Map
Sarasota, FL

What's nearby

  • Shell Beach - 2 min walk - 0.2 km
  • Irma Beach - 19 min walk - 1.6 km
  • Siesta Key Beach - 6 min drive - 4.1 km
  • Crescent Beach - 12 min drive - 8.6 km
  • Lido Beach - 18 min drive - 12.9 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 18 min drive

Restaurants

  • ‪Circle K - ‬4 min drive
  • ‪Sun Garden Cafe - ‬4 min drive
  • ‪The Old Salty Dog - ‬4 min drive
  • ‪The Hub Baja Grill - ‬4 min drive
  • ‪Drift Kitchen & Bar - Lido Beach Resort - ‬14 min drive

Frequently asked questions

Does Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven have a pool?

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

How much does it cost to stay at Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven?

As of 4 July 2026, prices found for a 1-night stay for 2 adults at Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven on 5 September 2026 start from NZ$810, 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 Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven pet-friendly?

No, pets are not allowed at this property.

How much is parking at Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven?

On-site parking is available at the property.

What time is check-in at Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven?

Check-in begins at 4:00 PM.

What time is check-out at Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven?

Checkout is at 10:00 AM.

Where is Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven located?

Located in Bay Isle, this holiday home is 0.2 mi (0.4 km) from Shell Beach and 2 mi (3.3 km) from Siesta Key Beach. Irma Beach and Siesta Key Farmers Market are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 20 out of 22 reviews
Rating 8 - Good. 2 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Allan F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A wonderful house, everything clean and responsive hosts. Would go back!
Stayed 4 nights in Dec 2025
Response from VrboOwner on 8 December 2025
Hi Allan, Thank you for your kind review! We’re happy to hear you enjoyed the home, found everything clean, and felt well supported by our team. We’d love to host you again anytime—come back and visit us soon! Regards, The CottageCrew
Verified

10/10 Excellent

June M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home with a heated pool. Very clean and comfortable with plenty of room to spread out. The property management company, The Cottages on the Key, is first rate and wonderful to deal with any issue that comes up. We were looking forward to using the pizza oven, but after watching the recommended video we were so intimidated we decided to spend a year in training before attempting our first pizza.
Stayed 7 nights in Feb 2026
Response from VrboOwner on 11 March 2026
Hi June, Thank you for your wonderful review! We’re so glad to hear you enjoyed the home, the heated pool, and the space to relax comfortably. It’s also great to know our team at The Cottages on the Key was helpful during your stay—we truly appreciate your kind words. And we completely understand about the pizza oven! It can feel a bit like a chef’s challenge at first, but we hope you’ll give it a try on your next visit. We’d love to welcome you back anytime! Regards, The CottageCrew
Verified

10/10 Excellent

Meg H.

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

Great stay

Wonderful house and lovely neighborhood. We would most definitely book again.
Stayed 6 nights in Mar 2025
Response from VrboOwner on 20 April 2025
Hi Meg, Thank you for the great review! We're thrilled you enjoyed the home and neighborhood. We'd be happy to host you again anytime! Regards, The CottageCrew
Verified

10/10 Excellent

Nancy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice house. Very clean. Agent seemed available if we needed anything. Very well appointed except for boxes of toiletries which had opened and were not usable.
Stayed 4 nights in Dec 2025
Response from VrboOwner on 31 December 2025
Hi Nancy, Thank you for your feedback. We’re pleased to hear you enjoyed the home’s cleanliness, comfort, and our team’s availability. We apologize for the issue with the opened toiletries and appreciate you bringing this to our attention. We’ve shared your comments with our housekeeping team and are reinforcing our inspections to ensure all amenities are fresh and ready for future guests. We hope to have the opportunity to host you again. Sincerely, Guest Services
Verified

10/10 Excellent

Verified traveller

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

Comfortable and relaxing stay

Well equipped and comfortable home made for a relaxing stay
Stayed 30 nights in Sep 2023
Response from VrboOwner on 3 November 2023
Dear Colin, Thank you for your kind words! We're delighted to hear that Hemingway House provided you with a well-equipped and comfortable home, making your stay relaxing. Your satisfaction is our top priority, and we're glad we could contribute to your enjoyable experience. If you ever plan to return to Siesta Key, we'd love to host you again. Feel free to reach out if you have any questions or need assistance in the future. Warm regards, The CottageCrew
Verified

10/10 Excellent

Rita W.

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

Girls trip

We loved it and we’ll be going back! The pool is nice!
Stayed 8 nights in May 2024
Response from VrboOwner on 13 June 2024
Hi Rita, Thank you for your wonderful feedback! We're thrilled to hear you enjoyed your stay at Hemingway House and loved the pool. We look forward to welcoming you back soon! Regards, The CottageCrew
Verified

10/10 Excellent

ed y.

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

Hemingway House

The house was great. We could have stayed forever!
Stayed 7 nights in Feb 2024
Response from VrboOwner on 5 March 2024
Hi Ed, Thank you for your wonderful feedback about your stay at Hemingway House! We're thrilled to hear that you had such a fantastic experience and that you enjoyed the house so much. It means a lot to us to know that our guests feel at home and want to stay longer. We look forward to welcoming you back anytime you're ready for another getaway. Until then, take care! Regards, The CottageCrew
Verified

10/10 Excellent

Dory J.

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

A piece of paradise.

Perfection in all aspects. You will definitely enjoy your stay here.Only thing I would add is that Shell beach, one block from the house, has been largely destroyed subsequent to last year's hurricane. Still a nice spot to watch the sunset.
Stayed 7 nights in Apr 2025
Response from VrboOwner on 2 May 2025
Hi Dory, Thank you for the wonderful review! We're so glad you enjoyed your stay and appreciate the note about Shell Beach—it's still a lovely sunset spot, even as it recovers. We hope to welcome you back soon! Regards, The CottageCrew
Verified

10/10 Excellent

Kelly B.

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

Family get away

Amazing week! The house was perfect for all 6 of us. Plenty of room to relax for the week. We loved the location. It was 2 miles fromsK village. Disappointed shell island was closed bc it would have been so nice to walk to the beach!
Stayed 6 nights in Mar 2025
Response from VrboOwner on 8 April 2025
Hi Kelly, Thank you so much for the kind words! We’re so glad to hear the house was a perfect fit for your group and that you had a relaxing week. The location really is great—close enough to enjoy Siesta Key Village while still offering a peaceful retreat. We totally understand your disappointment about Shell Island being closed—it’s such a beautiful spot, and we hope it reopens soon for future guests to enjoy. We’d love to host you again anytime! Regards, The CottageCrew
Verified

10/10 Excellent

Nicki M.

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

Perfect

Everything about this property, location and rental company was exceptional. We needed rest and relaxation and that’s exactly what we had from the moment we stepped through the door. We cannot recommend this property highly enough and we will definitely be back
Stayed 7 nights in Oct 2022
Response from VrboOwner on 15 November 2022
Hi Nicki, Thank you so much for sharing your amazing vacation experience at Hemingway House! We are absolutely thrilled to hear your vacation was nothing but relaxing and the peace & quiet you were looking for! We would love to host your stay again. When you do come back for another getaway to paradise, make sure that you redeem your return guest discount. (: With love, The Cottage Crew
Verified

10/10 Excellent

suzanne w.

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

FANTASTIC!!!

Thank you for EVERYTHING!! It was PERFECT!’ We also loved the heated pool! What a treat!! Great area!!! The property was managed beautifully!
Stayed 7 nights in Feb 2024
Response from VrboOwner on 19 March 2024
Hi Suzanne, Thank you so much for your enthusiastic feedback about your stay at Hemingway House! We're thrilled to hear that everything was perfect for you and that you enjoyed the heated pool as well as the surrounding area. Your kind words about our property management are truly appreciated. It was our pleasure to ensure your stay was enjoyable. We hope to have the pleasure of hosting you again in the future! Warm regards, The CottageCrew
Verified

10/10 Excellent

Phyllis R.

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

Fantastic property

We had a wonderful stay at this beautiful property.. it was immaculately clean. We had a problem with the AC and they fixed it immediately. Communication was top notch. We didn’t want to leave. We would definitely come back again. Thank you for a great stay 😊
Stayed 7 nights in Jun 2024
Response from VrboOwner on 27 June 2024
Hi Phyllis, Thank you for your kind words! We're delighted you enjoyed your stay at Hemingway House and appreciated our prompt service. We look forward to welcoming you back in the future! 😊 Regards, The CottageCrew
Verified

10/10 Excellent

William P.

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

Beautiful Hemingway House

Really lovely house in a convenient part of Siesta Key (north end), so convenient to town, beach and Sarasota. Most neiboring houses are not to the same standard, that is only a minor detraction.
Stayed 14 nights in Mar 2023
Response from VrboOwner on 29 March 2023
Hi William, Thank you so much for sharing your 5 star vacation experience with us! We are so happy to hear you enjoyed your stay at Hemingway House and got to take advantage of all the incredible amenities this home has to offer. We would love to host your stay again! (: With love, The Cottage Crew
Verified

10/10 Excellent

Liz C.

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

Perfect!

Hemingway House was perfect! The location was great .. close to the Siesta bridge. We were very comfortable and even used the pizza oven. It’s not so easy! Response to us was quick and immediate. I will say that supplies were limited… no start up food stuff in the kitchen. It was wonderful to get away!
Stayed 13 nights in Apr 2024
Response from VrboOwner on 27 May 2024
Hi Liz, Thank you for your fantastic feedback about Hemingway House! We're delighted to hear that you enjoyed the great location and felt comfortable during your stay. It's wonderful that you got to use the pizza oven! We appreciate your note about the kitchen supplies and will look into improving that. We're glad you had a wonderful getaway and look forward to hosting you again soon! Regards, The CottageCrew
Verified

8/10 Good

Jennifer G.

Liked: Cleanliness, check-in, communication
Disliked: Location

Beautiful but noisy...

Beautiful property. Very clean & plenty of room for our family of 5. Management was also extremely responsive. Only issue is location. Streets run in front of and in back of this house. Noise from construction, garbage trucks, landscapers is constant in the mornings. Not as peaceful as I had hoped.
Stayed 6 nights in Jul 2024
Response from VrboOwner on 24 September 2024
Hi Jennifer, Thank you for your feedback. We’re glad to hear you enjoyed the cleanliness and space at Hemingway House, as well as our responsive management. We apologize for the noise and appreciate your understanding. We’ll take your comments into consideration for future improvements. Regards, The CottageCrew
Verified

10/10 Excellent

Alisa M.

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

Beautiful Landscaping, and Peaceful Stay

Upon arriving the first impression was that this property was tucked away on a peaceful street, no traffic, and very quiet. The yard was filled with lush plants which helped with privacy. The interior was well decorated and nice easy flow to all of the rooms. Very clean! The kitchen was stocked with what appeared to be all new pots, pans, dishes. We cooked several meals here and had everything we needed. We did one meal on the grill outside. The patio area was very spacious as well. There were plenty of TV's on the property... 5 to be exact. There was a private office, which held a pullout sofa and tv. This room was very nice for someone needing to do remote work or for a study area. 5 minute drive to public beach. Very nice property!!
Stayed 7 nights in Mar 2023
Response from VrboOwner on 10 April 2023
Hi Alisa, Thank you so much for sharing your 5 star vacation experience with us! We are so happy to hear you enjoyed your stay at Hemingway House and got to take advantage of all the incredible amenities this home has to offer. The location is absolutely unbeatable being so close to the beach, shops and restaurant! We would love to host your stay again! (: With love, The Cottage Crew
Verified

8/10 Good

Travis&Kristin G.

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

Siesta Stay

We really enjoyed our stay at the Hemingway home. The lay out was great and the kitchen was well equipped with cooking necessities. The location was great- however we came 3 weeks post hurricane Milton and the street that the house was/is on- was a destruction zone. There was so much debris on the sides of the road it looked like a war zone. The Hemingway way home was thankfully unscathed but I am pretty sure the surrounding houses were sadly very affected. The only real negative about the house, for us, was the pool. Looking at the pictures I was really happy to see that there was a fence around it. We have a two year old and that made me feel more secure as far as safety goes. However once at the house and seeing/ experiencing it for ourselves - the fence is so tight against the pool there was little area to walk around it. And many of the tiles were uprooted and very unsafe to walk around for children. Not sure if that was a hurricane issue or not. We had our toddler in swim floaties and when walking around the pool the fencing was literally so close to the pool that her floaties were touching the fence as she walked around. So obviously - for the adults there was no room to lounge with chairs etc by the pool- and the pool was shaded by 12:30 daily. Although the house was very nice, the location was great and the rental owners were very responsive we wouldn't rent the house again based on the pool situation. We ended up using the beach more because of it.
Stayed 7 nights in Nov 2024
Verified

10/10 Excellent

Michelle D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our time at the Hemingway House. The property was clean, located in a great area and the property manager was top notch. The property is located a few miles from the Siesta Key beach. During our stay, we did not have any issues finding parking at the beach. There is mention in some of the older comments about being close to the beach, the reference is to a small beach area located a short walk from the property. This was originally a small beach area, but the hurricane in 2024 destroyed the small area that was there. There is a free trolley that has a stop close to this property, but it was easier for us to drive ourselves. There are bicycles located on the property for use, too. We loved the outdoor pizza oven! My family would definitely stay at this property again!
Stayed 7 nights in Jun 2026
Response from VrboOwner on 23 June 2026
Hi Michelle, Thank you so much for your thoughtful review! We’re delighted to hear you enjoyed your stay at Hemingway House and that the home, location, and service from our team all contributed to a great experience. We also appreciate you sharing your observations about the beach access and transportation options. Feedback like this can be very helpful for future guests planning their stay. Thank you again for choosing to stay with us. We’re thrilled to hear your family would return, and we look forward to welcoming you back for another memorable getaway in the future. Warm regards, Guest Services Team
Verified

10/10 Excellent

Valerie L.

Stayed 11 nights in Apr 2026
Response from VrboOwner on 8 June 2026
Hi Valerie, Thank you so much for your five-star rating! We truly appreciate you choosing to stay with us and are so glad you had a great experience. We hope to have the pleasure of welcoming you back again soon. Warm regards, Guest Services Team
Verified

10/10 Excellent

Julie M.

Stayed 7 nights in Mar 2026
Response from VrboOwner on 21 April 2026
Hi Julie, Thank you so much for your five-star rating! We truly appreciate you choosing to stay with us and are so glad you had a great experience. We hope to have the pleasure of welcoming you back again soon. Warm regards, Guest Services Team
Verified

10/10 Excellent

Vicki K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Don P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Mar 2024
Response from VrboOwner on 26 August 2024
Hi Don, Thank you for providing 5 star rating and we hope to welcome you back in Siesta Key. Regards, The CottageCrew

About the host

Hosted by The Cottages on the Key, Inc.

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