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Pineapple on Siesta Key

Vacation home near Siesta Key Beach in Siesta Key

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Photo gallery for Pineapple on Siesta Key

A modern kitchen with a stainless steel refrigerator, a dining area with a table and chairs, a large window with a view of greenery, and a ceiling fan.
A private dock with a sign stating "PRIVATE DOCK NO TRESPASSING."
A wooden dock leading to a calm water body, surrounded by lush greenery and residential buildings in the background.
A modern kitchen with grey cabinets, a central island, and a dining area with grey chairs.
A living room with a beige sofa, a wooden coffee table, a TV on a stand, and a window with a view of palm trees.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms4 bathrooms12917 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Free WiFi
  • Air conditioning
  • Parking available
  • Barbecue grill

Explore the area

View in a map
Siesta Key, FL
  • Place, Siesta Key Farmers Market
    ‪9 min walk‬
  • Place, Siesta Key Beach
    ‪12 min walk‬
  • Place, Siesta Key Beach Playground
    ‪3 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪28 min drive‬

Room options

About the neighborhood

Siesta Key

On waterfront.You'll find Siesta Key Beach and Siesta Key Farmers Market within a 15-minute walk of this Siesta Key vacation home. Siesta Key Beach Playground and Irma Beach are also within 2 miles (3 km).
View more Vacation Homes in Siesta KeyOpens in a new window

What's nearby

  • Siesta Key Farmers Market - 9 min walk - 0.5 miles
  • Siesta Key Beach - 12 min walk - 0.7 miles
  • Siesta Key Beach Playground - 3 min drive - 0.9 miles
  • Crescent Beach - 7 min drive - 3.2 miles
  • Turtle Beach - 10 min drive - 5.3 miles

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 37 min drive

Restaurants

  • ‪Circle K - ‬11 min walk
  • ‪Gilligan's Island Bar & Grill - ‬11 min walk
  • ‪Siesta Beach Pavilion - ‬3 min drive
  • ‪Siesta Key Oyster Bar - ‬10 min walk
  • ‪Daiquiri Deck Siesta Key Village - ‬11 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.

Pineapple on Siesta Key

Kick back and relax in this calm, stylish 3-bedroom, 4-full bathroom canal-front home, perfect for families or couples seeking a tranquil getaway. Just a short 5-minute walk away, you`ll find the vibrant Siesta Key Village, offering a variety of shops, restaurants, and entertainment. And, of course, you`re just minutes from Siesta Key Beach, consistently ranked as the #1 beach in the US!
Book your dream vacation today and experience the best of Siesta Key!`

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  • Parking included
  • Barbecue grill
  • Living/Dining area
5.0 out of 5, Exceptional, 1 review
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Property amenities

Beach

  • Beach nearby

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Bedrooms

  • 3 bedrooms

Bathroom

  • 4 bathrooms

Entertainment

  • Smart TV

Outdoor areas

  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • On the waterfront

Things to do

  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Parasailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby

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)
  • Fire extinguisher

General

  • Unit size: 12,917 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

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

Rules

Minimum age 25 without parents.

Pets

  • No pets allowed

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
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 and a smoke detector in each accommodation.

Property is also known as

357154

Frequently asked questions

How close is Pineapple on Siesta Key to the airport?

This vacation home is 10.5 mi (37-min drive) away from the Sarasota-Bradenton Intl. Airport (SRQ) airport, the closest popular airport to the property.

Does Pineapple on Siesta Key have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Pineapple on Siesta Key to the beach?

This vacation home is a short 13-minute walk from Siesta Key Beach and 10.7 mi (37-min drive) from Lido Beach. Don't forget your sunscreen!

Does Pineapple on Siesta Key offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Pineapple on Siesta Key?

No, there is no casino at this vacation home.

What time is check-in at Pineapple on Siesta Key?

Check-in begins at 3:00 PM.

Is there free parking at Pineapple on Siesta Key?

Free parking is not available at this vacation home.

Does Pineapple on Siesta Key have a pool?

This vacation home does not have a pool.

Does Pineapple on Siesta Key have a spa?

There are no spa services available at this vacation home.

How close is Pineapple on Siesta Key to downtown Siesta Key?

This vacation home is 0.4 mi away from Siesta Key.

Pineapple on Siesta Key Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 17 out of 17 reviews
Rating 8 - Good. 0 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

jill m.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location - walking distance to town and beach! Very comfortable stay for 5 adults and one child.
Stayed 6 nights in Mar 2026
Verified review

10/10 Excellent

Iosif B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Donna M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect place for couples 3 king beds and bathrooms for each room. All of the amenities you could ever need for cooking, for the beach and comfort. The beach and shops were close by and parking was adequate for vehicle and golf cart. We loved the patio, grill and pool area. I definitely would stay here again.
Stayed 5 nights in Apr 2026
Verified review

10/10 Excellent

adam s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was perfectly located for our stay. Easy walk into town and the beach. Parking was a breeze. Pool was spotless. Rooms were spacious and accomodatimg. Quiet area of neighborhood.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Sean E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was as advertised...very clean, great pool and the communication with the owners was great. Highly recommend
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Yvonne P.

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

Perfect!

Perfect stay! Location, clean and has everything you could ever need!
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

Kathleen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a wonderful property. The host was so kind and always responded to my million questions and gave us good information and tips about the area the house itself and everything you could need. It was very clean. The beds were very comfortable. The location was perfect. You could get to the beach or to any of the downtown area very quickly. We had the best time.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Nicole M.

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

Perfect getaway

This house was in the perfect location. Short walk to the beach and Siesta Village for shopping and restaurants. It was comfortable, clean, and quiet. The pool was perfect to relax at at the end of the day. Will stay here again if we come back to the area!
Stayed 4 nights in Mar 2025
Verified review

10/10 Excellent

Alyssa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful experience. Marcus and Nicki were very responsive when we need anything. The location was excellent walking distance to the village, but far enough you didn't hear the nightlife when wanting to go to bed. The beach chairs, umbrella, roller cart they provide was one less thing to worry about finding. Highly recommend staying here in the future!
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

lesley p.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nikki and Marcus were great to rent from! quick communication and everything was as expected! house was great and great location!! highly recommend!
Stayed 5 nights in Jul 2025
Verified review

10/10 Excellent

alejandra R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is very comfortable, the master bedroom is huge, it has a king size bed another bed definitely fits in there. The house had everything we needed. The pool is very nice, my kids loved it. The neighborhood is nice and quiet and min away from the village and beach. We rented a golfcart to get around and it was great. Marcus was quick to respond for any concerns. We are very pleased and would definitely stay there again.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Bruce P.

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

Great Stay

Great location. Very nice pool. Recently renovated so appliances are all new. Location close to the village yet far enough so it is quiet. Greatly appreciated condiments being left in the refrigerator. A lot of rentals make you remove everything when you leave. Nikki was very responsive to our questions.
Stayed 14 nights in Apr 2025
Verified review

10/10 Excellent

Dan P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Pineapple was a great house. Location was great too.
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

leslie c.

Stayed 5 nights in Mar 2026
Verified review

10/10 Excellent

Sarah O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Feb 2025

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