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Entire home

Pineapple on Siesta Key

Photo gallery for Pineapple on Siesta Key

Pool
Property grounds
Exterior
Private kitchen
Living area

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Free Wi-Fi

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

4 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

Kitchen

About this property

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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About the area

Siesta Key

Located in Siesta Key, this holiday home is on the waterfront. 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 St. Boniface Episcopal Church Labyrinth are also worth visiting. Discover the area's water adventures with scuba diving, snorkelling and parasailing nearby, or enjoy the great outdoors with ecotours.
View more Holiday homes in Siesta KeyOpens in a new window
Map
Siesta Key, FL

What's nearby

  • Siesta Key Farmers Market - 9 min walk - 0.8 km
  • Siesta Key Beach - 12 min walk - 1.1 km
  • Siesta Key Beach Playground - 3 min drive - 1.4 km
  • Crescent Beach - 7 min drive - 5.1 km
  • Lido Beach - 29 min drive - 18.9 km

Getting around

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

Restaurants

  • ‪Siesta Beach Pavilion - ‬3 min drive
  • ‪Siesta Key Snack Bar - ‬3 min drive
  • ‪Circle K - ‬11 min walk
  • ‪Gilligan's Island Bar & Grill - ‬11 min walk
  • ‪Sun Garden Cafe - ‬9 min walk

Reviews

10

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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

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

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

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

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

10/10 Excellent

Iosif B.

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

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

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

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

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

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

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

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

10/10 Excellent

leslie c.

Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Sarah O.

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