Entire home

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

Holiday home in Siesta Key with private pool and kitchen

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

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 8178.4 sq m

Popular amenities

  • Parking available
  • Air conditioning
  • Dryer
  • Washer
  • Outdoor space
  • Pool

Explore the area

View map
Sarasota, FL
  • Place, Shell Beach
    ‪2 min walk‬
  • Place, Siesta Key Beach
    ‪4 min drive‬
  • Place, Lido Beach
    ‪16 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪17 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.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 26
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

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 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 happening at Stardust Event Center or Ed Smith Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Sarasota, FL

What's nearby

  • Shell Beach - 2 min walk - 0.2 km
  • Siesta Key Beach - 4 min drive - 3.4 km
  • Crescent Beach - 9 min drive - 7.2 km
  • St. Armands Circle - 14 min drive - 12.2 km
  • Lido Beach - 16 min drive - 14.3 km

Getting around

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

Restaurants

  • ‪Circle K - ‬4 min drive
  • ‪Drift Kitchen & Bar - Lido Beach Resort - ‬14 min drive
  • ‪Sun Garden Cafe - ‬4 min drive
  • ‪Tiki Bar at Lido Beach Resort - ‬15 min drive
  • ‪Star Thai & Sushi, Seista Key - ‬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.

Is Hemingway House | Serene Siesta Key Getaway with Heated Pool, Pizza Oven pet-friendly?

No, pets are not allowed at this 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).

About the host

Hosted by The Cottages on the Key, Inc.

Host profile image

Languages:

English, French, German, Dutch

Premier Host

They consistently provide great experiences for their guests