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Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops!

Photo gallery for Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops!

Enjoy evenings on the lanai after a fun day at the beach!
Pineapple Cove has a screened lanai so you can enjoy a bit of fruit & wine in the fresh air.
Queen sofa sleeper so 4 people can enjoy this adorable beach get-a-way
Book a romantic get-a-way for two....ensuite bath and new Roku TV with cable.
Stocked kitchen makes it really convenient to whip up your favorite meals at home if you prefer.

Reviews

9.6 out of 10
Exceptional
1 bedroom1 bathroomSleeps 464.5 sq m

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Deck or patio
  • Free Wi-Fi

Explore the area

View map
Sarasota, FL
  • Place, Crescent Beach
    ‪4 min walk‬
  • Place, Siesta Key Marina
    ‪8 min walk‬
  • Place, Siesta Key Beach
    ‪15 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪30 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Living Room

1 Queen Sofa Bed

Master

1 Queen Bed

1 bathroom

En-Suite

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Number of living rooms
Dining area

About this property

Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops!

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savings

Welcome to Pineapple Cove!



Experience the best of Siesta Key at Pineapple Cove, a beautifully updated one-bedroom retreat on the vibrant south end of the island. Whether you’re here for a week of sun-drenched relaxation, a solo coastal getaway, or a small family beach break, this ground-floor condo puts you right where you want to be.



LOCATION HIGHLIGHTS

Skip the parking hassle! You are perfectly positioned for a car-free vacation:

- Beach Access: A breezy 6-minute stroll to Crescent Beach (Access #12 & #13).

- Nature’s Beauty: 7 minutes to the famous Point of Rocks for snorkeling and scenery.

- Island Life: Walkable to local favorites like Captain Curt’s, Big Water Fish Market, and the Orange Octopus for dessert - just a few minutes from your doorstep!

- Easy Transport: Hop on the free Siesta Key Breeze Trolley nearby for a stress-free ride to Siesta Village for more shopping and dining.



THE SPACE

- Living: Open, beach-themed living area featuring a queen sleeper sofa and a screened lanai. The perfect spot for morning coffee in the salt air.

- Rest: A serene Master Suite with a cooling queen mattress and wall-mounted Roku TV.

- Kitchen: Fully equipped for beachside brunch or a quiet dinner at home, with dining seating for four.

- Perks: Dedicated High-Speed WiFi, beach chairs, umbrella, and towels are all provided.



AT A GLANCE:

- Sleeps: Up to 4 guests.

- Convenience: Ground floor unit, bike rack, and communal laundry.

- No smoking/vaping

- No pets

- Self check in with keyless lock



Discover your perfect Siesta Key rhythm. Book your stay at Pineapple Cove today!

We help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.



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Feel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.

IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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 no carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Siesta Key

Located near the beach, this condo is in South Village, 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 going on at Ed Smith Stadium, or consider a night out at Venice Train Depot. Discover the area's water adventures with jet skiing, snorkelling and sailing nearby, or enjoy the great outdoors with cycling.
Map
Sarasota, FL

What's nearby

  • Crescent Beach - 4 min walk - 0.4 km
  • Siesta Key Marina - 8 min walk - 0.7 km
  • Siesta Key Beach - 15 min walk - 1.3 km
  • Gulf Gate Mall - 3 min drive - 2.4 km
  • Lido Beach - 23 min drive - 17.1 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 33 min drive

Restaurants

  • ‪Panera Bread - ‬3 min drive
  • ‪McDonald's - ‬2 min drive
  • ‪Hooters - ‬3 min drive
  • ‪Taco Jalisco - ‬3 min drive
  • ‪Captain Curt's Crab & Oyster Bar - ‬5 min walk

Frequently asked questions

Is Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops!?

As of 10 Apr 2026, prices found for a 1-night stay for 2 adults at Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops! on 29 May 2026 start from AU$285, 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.

How much is parking at Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops!?

On-site parking is available at the property.

What time is check-in at Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops!?

Check-in begins at 3:00 PM.

What time is check-out at Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops!?

Checkout is at 10:00 AM.

Where is Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops! located?

Located in South Village, this condo building is within 1 mi (2 km) of Crescent Beach and Siesta Key Beach. Siesta Key Marina and Point of Rocks are also within 10 minutes.

Reviews

9.6

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. 31 out of 39 reviews
Rating 8 - Good. 6 out of 39 reviews
Rating 6 - Okay. 2 out of 39 reviews
Rating 4 - Poor. 0 out of 39 reviews
Rating 2 - Terrible. 0 out of 39 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Lanny & Kristin G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communication, information and amenities!
Stayed 3 nights in Feb 2026
Response from VrboOwner on 5 Mar 2026
You were awesome guests! Please don't be strangers, we would love to host you again! Best Regards, iTrip Sarasota and Venice
Verified

6/10 Okay

Don B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Communication was very good and helpful. Location was good. Unit was overall very clean. Mattress was unlevel which negatively impacted our sleep during the stay. Would have rated a 4-star otherwise.
Stayed 4 nights in Feb 2026
Response from VrboOwner on 25 Mar 2026
Thank you for your review! We’re glad to hear you found the communication helpful, enjoyed the location, and that the unit was clean overall. We’re sorry to hear the mattress affected your comfort and sleep during your stay. Your feedback has been shared with our team so it can be inspected and addressed. We appreciate you choosing to stay with us and hope to have the opportunity to host you again in the future. Best Regards, iTrip Sarasota and Venice
Verified

8/10 Good

Barry B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Easy check in little confusing on location not a big deal but the stove is not working yes would return again.
Stayed 4 nights in Mar 2026
Response from VrboOwner on 25 Mar 2026
Thanks for your review and letting us know about the stove. It was a tripped breaker and all is working fine now. We appreciate you staying with us and would love to host you again! Best Regards, iTrip Sarasota and Venice
Verified

10/10 Excellent

DAVID

Liked: Cleanliness, property conditions & facilities
Very clean and nicely decorated. It is in a great location with easy access to restaurants and Cresent Beach. It had a very beachy look that we really liked.
Stayed 4 nights in Jun 2025
From a partner site

10/10 Excellent

Gustavo

Loved the Place

I love all the house and the vacation. The furniture is very clean. Its very comfortable.
Verified

10/10 Excellent

Dona T.

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

Great place

We loved it
Stayed 6 nights in Feb 2025
Verified

8/10 Good

Michael S.

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

Our stay

loved the location - close to restaurants, beach and ice cream!!
Stayed 21 nights in Feb 2023
Response from VrboOwner on 6 Sept 2023
Thank you for your review! If there is anything we can do it make it 5 stars, please don't hesitate to reach out. We would love to host you again. Best Regards, Anh, iTrip Sarasota Beach Vacations
From a partner site

10/10 Excellent

Patricia S.

very pleased

Condo was comfortable and a great location.
Verified

10/10 Excellent

carol D.

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

Beautiful quiet area

You can walk to beach and many restaurants in the area. Place was roomy and clean.
Stayed 14 nights in Mar 2023
Response from VrboOwner on 6 Sept 2023
Thank you for choosing to stay with us and we hope to see you again!
From a partner site

10/10 Excellent

Michelle

Walk 6 Minutes to Crescent Beach, Walk to Cafes

We loved the decor of the condo, the fact that beach items were supplied and the beautiful and convenient location!
Verified

10/10 Excellent

Linda K.

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

Vacation 11/20/2023

Very nice, quiet and easily accessible.
Stayed 8 nights in Nov 2023
Response from VrboOwner on 14 Dec 2023
Thanks Linda! We appreciate you staying with us. Anh, iTrip Sarasota and Venice
From a partner site

10/10 Excellent

Abby H.

Repeat Renter - Home Away from Home

I've lost count how many times we have stayed at Pineapple Cove. It feels like home away from home to our family. The kids love the light up palm trees & us adults like the access to the beach, trolley, & food. We are always comfortable staying here! Thank you!
Verified

10/10 Excellent

James H.

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

Nice place for two.

Very good. Nice place to stay for two.
Stayed 11 nights in Apr 2023
Response from VrboOwner on 6 Sept 2023
We are glad you enjoyed the property! Thank you, Anh, iTrip Sarasota Beach Vacations
Verified

10/10 Excellent

Jen F.

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

Pineapple Cove

The location was perfect! Short walk from the beach and things to do in town. Perfect amount of space for us as we vacationed in Siesta Key! Would definitely come back!
Stayed 5 nights in Jul 2022
Response from VrboOwner on 6 Sept 2023
Thank you for choosing us and we hope to see you again!
Verified

10/10 Excellent

Janna R.

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

Perfect beach home

We thoroughly enjoyed our stay at this little beach condo! It was clean and had all the basics, and we loved the beachy vibe. Just minutes from the beach and walkabale to several restaurants and bars. Highly recommend!
Stayed 4 nights in Aug 2022
Response from VrboOwner on 6 Sept 2023
We loved hosting you Janna! Best Regards, iTrip Sarasota and Venice
Verified

10/10 Excellent

Mary D.

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

Everything you need

We enjoyed our stay so much! Great location to the beach and restaurants! Clean and decorated cute! Equipped with everything we needed to enjoy a week away from home.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 6 Sept 2023
We are so glad you enjoyed your stay! Best Regards, iTrip Sarasota and Venice
From a partner site

10/10 Excellent

Larry E.

Loved Our Stay!

We loved our stay here! The unit decor was fun and inviting. We found everything we needed. The beach umbrella & chairs were an excellent addition! Everything was clean and the bed was so comfortable. We were close to all of the activities, food and shopping.
Verified

10/10 Excellent

Darren G.

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

Siesta Key

Condo was great. Just a couple blocks to beach/bars/restaurants
Stayed 9 nights in Jan 2023
From a partner site

10/10 Excellent

Tekoa G.

Great Location, Clean

Great location. Everything was clean. This complex was quiet which was very nice. We appreciated the beach supplies, cooler, etc.
Stayed 7 nights in Apr 2022
Verified

10/10 Excellent

Lisa F.

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

Wonderful Siesta Condo

Had a great week in this clean and cute condo! Walked to the beach to witness the amazing sunsets. Even extended our stay a couple of nights without any hassle or issues.
Stayed 8 nights in Aug 2022
Response from VrboOwner on 6 Sept 2023
We enjoyed hosting you! Best Regards, Anh, iTrip Sarasota and Venice
Verified

10/10 Excellent

Mark P.

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

Siesta Key 1st timer

Property worked out fantastic, easy beach access, and had all the beach stuff needed! Clean and comfortable
Stayed 14 nights in May 2023
Response from VrboOwner on 6 Sept 2023
We are glad you enjoyed it! Thank you for your review, Anh, iTrip Sarasota Beach Vacations
From a partner site

10/10 Excellent

Abby

Walk 6 Minutes to Crescent Beach, New Furnishings, WiFi, Parking, Walk to Restaurants

This is our 3rd staying here! It feels like home away from home now. I love how the unit is fully equipped with everything, a home needs. It is especially helpful for kids traveling - they love the palm trees and beach wagon. It's a convenient walk to beach and trolley too
Verified

10/10 Excellent

Abby H.

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

Above and Beyond Expectations

Awesome experience! Staff went above and beyond to ensure a comfortable stay and convenient check-in. Unit was clean, cozy & wide variety of amenities. Location is excellent- quick walk to the beach, trolley comes by every 20 minutes, and eateries right around the corner. Loved everything about staying here! Plan on making it our annual stay!
Stayed 5 nights in Oct 2021
Response from VrboOwner on 6 Sept 2023
We were so happy to host you and look forward to your return.
Verified

10/10 Excellent

Kevin G.

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

OUTSTANDING!!!

We have vacationed a lot in Florida, this was by far the best "bang for your buck" accommodations we have ever had! You will not be disappointed, very nice location, 2 blocks from the beach, 1 block from 7/11, Captain Curt's restaurant/bar/ lounge only 3 blocks. You will not find cleaner and more beautiful beaches any where!!!!
Stayed 7 nights in May 2023
Response from VrboOwner on 6 Sept 2023
Thank you so much Kevin! It was lovely to hot you! Best Regards, Anh, iTrip Sarasota Beach Vacations
From a partner site

10/10 Excellent

Aislyn

So Very Clean!

The blinds were unable to be moved throughout the stay but it was so incredibly clean! Seriously so clean. Very nice AC in unit and awesome that it came w/ all the beach items for 2! Would happily book again.

About the host

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