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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

9.8 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 81920 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Sarasota, FL
  • Place, Shell Beach
    ‪2 min walk‬
  • Place, Irma Beach
    ‪19 min walk‬
  • Place, Siesta Key Beach
    ‪4 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪24 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.
Our prices include all fees. No hidden fees.

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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

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Siesta Key

Located in Bay Isle, a neighbourhood in Siesta Key, this holiday home is near a water park and near the beach. 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. Mote Marine Laboratory & Aquarium and Coconuts Family Entertainment Center are also worth visiting. 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 - 4 min drive - 3.4 km
  • Crescent Beach - 8 min drive - 7.6 km
  • Lido Beach - 17 min drive - 12.5 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 Hub Baja Grill - ‬4 min drive
  • ‪Drift Kitchen & Bar - Lido Beach Resort - ‬14 min drive
  • ‪The Old Salty Dog - ‬4 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 2 May 2026, prices found for a 1-night stay for 2 adults at Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven on 30 Jul 2026 start from £257, 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

9.8

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. 18 out of 20 reviews
Rating 8 - Good. 2 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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

Julie M.

Stayed 7 nights in Mar 2026
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

About the host

Hosted by The Cottages on the Key, Inc.

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Languages:

English, French, German, Dutch

Premier Host

They consistently provide great experiences for their guests
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