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Hemingway House

Name: Hemingway House - 117
Brand: The Cottages on the Key
SKU: hemingway-house-117
Rating: 5.0 (20 reviews)

Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!

Bedrooms: 3

Bathrooms: 2 Full, 1 Half

Sleeps: 8

Step into your private retreat—this heated pool is the heart of the home, framed by tropical landscape and Florida sunshine.

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Exclusive Amenities Include: ↑↓

• Private Heated Pool & Screened Lanai With Outdoor Lounge
• Mediterranean-Inspired Wood-Burning Pizza Oven & Gas Grill
• 2.1 Miles to Beach Access 5 & 3 Miles to Siesta Key Beach
• Private Outdoor Shower With Bench Seat
• GE Café Refrigerator With Built-In Keurig
• Private 2-Car Garage
• Free WiFi & Multiple HDTVs
• In-House Washer/Dryer Laundry
• Regular & Keurig Coffee Makers, Dishwasher & Kitchen Essentials Provided
• Starter Pack of Toiletry Essentials – Shampoo, Conditioner, Hand/Face Soap, Body Lotion & Makeup Wipes
• Starter Pack of Home Essentials – Dish Soap, Sponge, Dishwasher Tablets, Laundry Pods & Cleaning Wipes
• Beach Towels, Chairs, Cooler & Caddy Provided + Enhanced Cleaning Protocols by Our CottageClean™ Team

Overview ↑↓

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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Reviews ↑↓

Total reviews: 20

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Review Date: June 14, 2026

"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!

Reviewed By: Michelle

Response from The Cottages on the Key:
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

Review Date: May 28, 2026

Reviewed By: Valerie

Response from The Cottages on the Key:
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

Beautiful home with a heated pool.

Review Date: March 11, 2026

"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.

Reviewed By: June Millar

Would go back!

Review Date: December 8, 2025

"A wonderful house, everything clean and responsive hosts. Would go back!

Reviewed By: Allan Ferguson

We'll most definitely look at using The Cottages again on our next visit.

Review Date: October 10, 2025

"What a beautiful home! We absolutely loved the privacy but also how close it was to what Siesta Key offers. The amenities of the home were amazing and has everything that you need. We loved the heated pool and the bikes the home has available. We’ll most definitely look at using The Cottages again on our next visit.

Reviewed By: Spencer Bebout

The Cottages on the Key supervise the property perfectly

Review Date: September 22, 2025

"The entire two weeks at Hemingway House, Siesta Key, was a peaceful retreat and a beautiful home to host my son and daughter-in-law from London. We began our days in the pool surrounded by superb landscaping and shaded by ancient Live Oaks; we took the island trolley to restaurants in Siesta Village; we drove to the other Keys and shopped in Sarasota; we ended every day with a sunset at Shell Beach, a block from the house. We cooked in the fully furnished kitchen and outdoor pizza oven, we relaxed on the screened-in lanai chatting late into the nights. The Cottages on the Key supervise the property perfectly, always there when we needed anything. I am pleased to recommend this AirB&B.

Reviewed By: Susan Jane Guiher

Perfection in all aspects.

Review Date: May 2, 2025

"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.

Reviewed By: Dory Jewelewicz

Wonderful house and lovely neighborhood.

Review Date: April 20, 2025

"Wonderful house and lovely neighborhood. We would most definitely book again.

Reviewed By: Meg Herdrich

Plenty of room to relax for the week.

Review Date: April 8, 2025

"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 from SK village. Disappointed shell island was closed bc it would have been so nice to walk to the beach!

Reviewed By: Kelly Britt

Our stay was fantastic!

Review Date: March 17, 2025

"Our stay was fantastic! We totally enjoyed the property, the pool was at a perfect temperature, we had our grandson with us he sure enjoyed the pool, our host was very responsive to any questions we had. I would definitely stay at this property again.

Reviewed By: Chris Snarski

Communication was top notch.

Review Date: June 27, 2024

"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 😊

Reviewed By: Phyllis Rubin

We loved it and we'll be going back!

Review Date: June 13, 2024

"We loved it and we'll be going back! The pool is nice!

Reviewed By: Rita Wendt

It was wonderful to get away!

Review Date: May 27, 2024

"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!

Reviewed By: Liz Cooper

The property was managed beautifully!

Review Date: March 19, 2024

"Thank you for EVERYTHING!! It was PERFECT!' We also loved the heated pool! What a treat!! Great area!!! The property was managed beautifully!

Reviewed By: Suzanne Whayne

Hemingway House was a perfect

Review Date: March 7, 2024

"Hemingway House was a perfect delight for celebrating my sister's 75th birthday. The delicious cupcakes welcomed us upon our arrival. It was wonderful to have access to bicycles and beach chairs. The heated salt water pool was a wonderful surprise, as well. Overall, a beautiful home for our sister trip!

Reviewed By: Sally Fife

We could have stayed forever!

Review Date: March 5, 2024

"The house was great. We could have stayed forever!

Reviewed By: Ed Young

Wonderful week spent at Hemingway House

Review Date: February 29, 2024

"We celebrated my oldest sister's 75th birthday with family in Siesta Key. Hemingway House made the perfect location for all of us. The house, pool and yard were wonderful and made our sister stay so relaxing. We had the best time spending the week with each other.

Reviewed By: Sally Fife

Well equipped and comfortable home

Review Date: November 3, 2023

"Well equipped and comfortable home made for a relaxing stay

Reviewed By: Colin Masterson

Beautiful Landscaping, and Peaceful Stay

Review Date: March 27, 2023

"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!

Reviewed By: Alisa Marciniak

Perfect

Review Date: November 15, 2022

"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

Reviewed By: Nicki Mayhew