See all properties
Entire home

Siesta Key Waterfront Estate heated Pool Privacy!

Vacation home near Siesta Key Beach in Sarasota

Choose dates to view prices

Photo gallery for Siesta Key Waterfront Estate heated Pool Privacy!

Beach
TV, fireplace, stereo
Fridge, microwave, oven, stovetop
Beach
4 bedrooms, desk, iron/ironing board, free WiFi

Reviews

9.0 out of 10
Wonderful

Entire home

4 bedrooms4 bathroomsSleeps 14

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Sarasota, FL
  • Place, The Landings
    ‪15 min walk‬
  • Place, Bee Ridge Park
    ‪5 min drive‬
  • Place, Coconuts Family Entertainment Center
    ‪5 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪27 min drive‬

Room options

You may also like

Ad
Property amenity

The St. Regis Longboat Key Resort

Longboat Key
  • On private beach
  • Pool
  • Hot tub
  • Spa
4.9 out of 5, Exceptional, 76 reviews
$1,055 nightly
The price is $1,192
Jun 30 - Jul 1
Total with taxes and fees
The St. Regis Longboat Key Resort

About the neighborhood

Sarasota

South Sarasota stay.Your stay at this South Sarasota vacation home places you within 2 miles (3 km) of The Landings and Bee Ridge Park. Sarasota Memorial Health Care System and Gulf Gate Mall are also within 3 miles (5 km).
View more Vacation Homes in SarasotaOpens in a new window

What's nearby

  • The Landings - 15 min walk - 0.8 miles
  • Bee Ridge Park - 5 min drive - 1.5 miles
  • Coconuts Family Entertainment Center - 5 min drive - 2.2 miles
  • St. Armands Circle - 22 min drive - 9.3 miles
  • Lido Beach - 23 min drive - 9.7 miles

Getting around

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

Restaurants

  • ‪Walt's Fish Market - ‬2 min drive
  • ‪Olive Garden - ‬14 min walk
  • ‪Origin Craft Beer & Pizza Cafe The Landing - ‬16 min walk
  • ‪Starbucks - ‬17 min walk
  • ‪Peachey’s Baking Company - ‬14 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Siesta Key Waterfront Estate heated Pool Privacy!

This wooded property is unreal and our 5 star ratings agree! 1 acre on the water for your entire family or group to relax and enjoy. Go swimming in the huge heated pool or go to the water and enjoy paddle boarding or kayaking to the Gulf of Mexico! After a long day at the beach unwind with a great fire pit! Play your music with no neighbors complaining. Every guest says the same thing "I was so relaxed I needed this! The property is tranquility at its BEST! Boating options available.

Go look at the other listings and look at the map! You will see that you are on an estate property and the others are right next to their neighbor and no parking here you have privacy and isnt that what you want??? You have plenty of parking and have your friends stop over plenty of room and privacy for everyone. The 4 bedrooms all have a separate blow up top of the line mattress with built in air compressor. The couch is amazing and can sleep 2-3 people and the second couch is a pull out queen sleeper sofa that can sleep 2. So each bedroom you can add one of the blow up mattresses or there are other areas where they can be placed for privacy. The additional beds listed are ALL blow up mattresses so you can move them to what works best for you but there is ONLY one bed per room + the 4 blow up mattresses.

You are 5 minutes from everything! We are 5 Minutes from the beach, downtown, crazy good location and hidden in the woods.

This is one of the last of the large wooded lots in Sarasota close to Siesta Key on the water. Private drive on the water Kayak, Paddle Board enjoy

You can park 10-20 cars no problem

This is great for a wedding or decent size event Ask us about boating from the back yard to the Gulf of Mexico
Our house rules are simple. Use ALL THE Amenities!! Use the fire pit, kayaks, paddle boards, corn hole, pool, BBQ if you do you will LOVE it like everyone else! If you are planning a party please reach out first for approval ANY guest over 12 people is $50 per person even if they are not staying the night. Pets are allowed and a pet fee is required.


The WiFi and extenders are all over the house so the WiFi is 600/600 extremely fast. Each room has a separate AC/heater just make sure you turn it to 75 each time you leave as they work extremely fast and you will be freezing in no time. The pool is set to 80 degrees. There are washers and dryer’s to use as well.

Similar properties

Outdoor pool
Carlisle Inn
Pinecraft
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
5.0 out of 5, Exceptional, 2,358 reviews
$151 nightly
The price is $171
Jun 4 - Jun 5
Total with taxes and fees
Carlisle Inn

Property amenities

Pool/Spa

  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 4 bathrooms
  • Hair dryer

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Stereo
  • TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Firepit
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the waterfront

Things to do

  • Gym
  • Kayak

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • Pets are welcome
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property is also known as

Siesta Key Paradise on the Water Great Pool
Siesta Key Cottage on the water great pool 5 star rated
Siesta Key Paradise on the Water Great Pool 5 Star Rated
Siesta Key Guest House on the Water Great Pool 5 Star Rated
102582

Frequently asked questions

How close is Siesta Key Waterfront Estate heated Pool Privacy! to the airport?

This vacation home is 8.9 mi (18-min drive) away from the Sarasota-Bradenton Intl. Airport (SRQ) airport, the closest popular airport to the property.

How much does it cost to stay at Siesta Key Waterfront Estate heated Pool Privacy!?

As of Jun 3, 2026, prices found for a 1-night stay for 2 adults at Siesta Key Waterfront Estate heated Pool Privacy! on Jul 1, 2026 start from $1,258, 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.

Does Siesta Key Waterfront Estate heated Pool Privacy! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Siesta Key Waterfront Estate heated Pool Privacy! to the beach?

This vacation home is 4.4 mi (7-min drive) from Siesta Key Beach and 8.9 mi (31-min drive) from Lido Beach. Don't forget your sunscreen!

Does Siesta Key Waterfront Estate heated Pool Privacy! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Siesta Key Waterfront Estate heated Pool Privacy!?

No, there is no casino at this vacation home.

What time is check-in at Siesta Key Waterfront Estate heated Pool Privacy!?

Check-in begins at 4:00 PM.

Is there free parking at Siesta Key Waterfront Estate heated Pool Privacy!?

Free parking is not available at this vacation home.

Does Siesta Key Waterfront Estate heated Pool Privacy! have a pool?

Yes, there's a private pool.

Does Siesta Key Waterfront Estate heated Pool Privacy! have a spa?

There are no spa services available at this vacation home.

How close is Siesta Key Waterfront Estate heated Pool Privacy! to downtown Sarasota?

This vacation home is 3.7 mi away from Sarasota.

Siesta Key Waterfront Estate heated Pool Privacy! Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 12 out of 14 reviews
Rating 8 - Good. 0 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 1 out of 14 reviews
Rating 2 - Terrible. 1 out of 14 reviews

8.8/10

Cleanliness

Reviews

Verified

10/10 Excellent

Karen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is in a great location, very clean and welcoming. Our fur baby (large dog) had a great time too!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Nelson F.

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

Roy made us feel at home

Very enjoyable stay
Stayed 2 nights in Feb 2023
Verified

10/10 Excellent

Roxana Q.

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

Excellent location

We enjoyed this beautiful home. The location was perfect. It was close to the beach and stores.
Stayed 2 nights in Jun 2024
Verified

10/10 Excellent

JAMES L C.

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

Family Vacation

A Good time.
Stayed 5 nights in Dec 2024
Verified

10/10 Excellent

LAMANH S.

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

Memorial Day Weekend Trip

The rental property met all our family needs. The property was spacious, had a pool, and access to waterfront for fishing, kayaking, and paddle boards. We were very satisfied with our stay.
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Megan M.

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

House worked perfectly for our family

We had a wonderful stay at this house! Roy was the BEST host, pool was heated and perfect. The access to the waterfront was amazing- we rented his boat for 3 days and he was extremely helpful. We would stay there again!
Stayed 6 nights in Mar 2024
Verified

10/10 Excellent

kurt s.

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

Excellent

The amenities and location made our stay a very memorable one. You are given access to the kayaks the fire pit and the pool and the host allowed us to borrow additional things that made our beach trips really enjoyable! Thank you!
Stayed 7 nights in Feb 2022
Verified

10/10 Excellent

Pamela T.

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

Serenity

Absolutely the most beautiful tucked away private spot! The owner Roy was super friendly and always available for anything. Cottage was immaculate and amenities were perfect! Great getaway! Highly recommend!!! Definitely going back!!
Stayed 2 nights in Sep 2021
Verified

10/10 Excellent

Heather H.

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

Family Vacation

This property has everything listed and more. We had 9 people with us and there was more than enough space and amenities for all to enjoy. The pool where the kids spent the majority of their time is amazing. The location is wonderful if you want privacy. The house feels like home the minute you arrive. I can't say enough positive about our host Roy. He was always available by phone or text, and often checked in to see if we needed anything. He is outstanding. We will return again next year.
Stayed 5 nights in Feb 2023
Verified

2/10 Terrible

Estela H.

Disliked: Cleanliness, communication, location, listing accuracy
This property did not match the listing or the standard expected for a paid short term rental. Upon arrival, the home was dirty and poorly maintained, including stained pillows, visibly dirty furniture, debris in bathrooms, unpleasant odors, and food left out, plastic tarp on roofSeveral aspects of the home were not clearly disclosed, including a bedroom located in the garage, and another on the patio, lack of bathroom privacy, visible dirty wiring, and overall conditions that made the home feel unsuitable for guests. made us feel like we were intruding rather than staying in a guest ready rentalWe checked out early and requested a refund only for the unused nights, which the host refused to return.More concerning was the host’s behavior after checkout. Instead of addressing the issues, the host became hostile and intimidating, referencing attorneys and stating that our family was recorded on cameras. This made us extremely uncomfortable as guests.We stayed elsewhere afterward. Based on cleanliness, transparency, and host conduct, we would not stay here again and would advise future guests to proceed with caution
Fitness facilities aka garage
Gym
Patio
Gym
Stayed 8 nights in Dec 2025
Verified

10/10 Excellent

Karen L.

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

Paradise in South Sarasota

This little cottage nestled between large live oaks and Florida fauna is a wonderful place to rest and play. The house includes every amenity from shampoo to a comfy bed and even a tiny dishwasher. The river is only steps away and accessible from the dock. There is a wonderful new hot tub which is 20 foot long and features a swimming option. Just awesome. You could spend the day reading on the porch on the couch or watching fish jump in the lagoon or pick up a paddle and head up river. I could go on but most importantly is the host Roy who truly cares about making your stay comfortable and attend to requests immediately. We have never had such a wonderful host. Thank you Roy for letting us enjoy this wonderful paradise in South Sarasota.
Stayed 30 nights in Mar 2022
Verified

10/10 Excellent

Verified traveler

Stayed 3 nights in Apr 2025