3 bedrooms
•
3 beds
•
3 bathrooms
•
8 guests
•
New
•
462.8477 sq. ft.
Operated by a Wander partner
Trusted operators, vetted by Wander
This unique combination of three homes offers a total of 3 bedrooms, is in a prime location, and has EVERYTHING you need for an amazing vacation in Sarasota, FL!
• Shared Outdoor Patio
• Fire Pit
• Hammock
• Dedicated Workspace
• Fully Stocked Kitchen
• Drip & Keurig Coffee Maker
• Plush Beds
• High Speed WIFI
• Family Friendly-High Chair & Pack ’n Play
• Dog Friendly
• Street Parking
Welcome to Pineapple Paradise #1–3, a unique Sarasota retreat comprising three private homes combined into one stay, perfectly designed for groups seeking space, privacy, and a prime location.
This thoughtfully arranged getaway offers a total of 3 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests—ideal for families, friends, or couples traveling together who appreciate having separate spaces under one booking.
Located in the heart of downtown Sarasota, you’re just minutes from world-class beaches, vibrant dining, shopping, arts, and nightlife. Whether you’re heading to Lido Beach, exploring St. Armands Circle, or enjoying Sarasota’s cultural scene, Pineapple Paradise places you close to it all while providing a relaxed home base to unwind.
Enjoy the flexibility of multiple living spaces, the convenience of a central location, and the charm of a one-of-a-kind setup. This is your perfect Florida escape!
MAIN SPACES OF THE HOME:
– 3 BEDROOMS & 3 BATHROOMS –
Pineapple Paradise #1
BEDROOM 1:
Pineapple Paradise #2
BEDROOM 2:
Pineapple Paradise #3
BEDROOM 3:
– 3 BATHROOMS –
– CHEF’S KITCHEN –
– LIVING ROOM –
Bedroom
1 full bed
Bedroom
1 full bed
Bedroom
1 full bed
Bedroom
1 full bed
Bedroom
1 full bed
Bedroom
1 full bed
Be the first to review this place.
Sarasota, Florida 34236, US
Sarasota, Florida, USDetwiler’s Farm Market is a lively local market known for fresh produce, seafood, meats, and baked goods. Its friendly, hometown feel and old-fashioned hand-dipped ice cream make it a welcoming stop.
Marina Jack is a beloved Sarasota waterfront restaurant serving fresh seafood and classic coastal fare with sweeping bay views. Its mix of elegant dining rooms, lively patio seating, and sunset vibes makes it a standout bayfront destination.
Columbia Restaurant is a Florida icon serving traditional Spanish and Cuban cuisine in a historic, old-world setting. Known for signature dishes, sangria, and rich family-run charm, it blends timeless ambiance with a lively dining experience.
Walt’s Fish Market Restaurant is a laid-back Sarasota seafood spot serving fresh catches, classic coastal favorites, and tiki-bar vibes. Its long history and market-meets-restaurant feel give it an easygoing, local charm.
St. Armands Circle offers a lively mix of waterfront-inspired dining, from classic Cuban and Spanish fare to fresh seafood and casual tropical spots. Its palm-fringed, walkable setting gives every meal a relaxed Sarasota vacation feel.
Dry Dock Waterfront Grill serves fresh seafood and American coastal favorites in a relaxed, polished-casual setting. Its al fresco waterfront dining and Sarasota Bay views make it a standout Longboat Key spot.
Yoder’s Restaurant serves hearty Amish comfort food in a warm, friendly setting, known for homemade dishes, baked goods, and award-winning pies. It’s a classic spot for simple, down-home cooking.
Owens Fish Camp serves Southern-style seafood and classic coastal favorites in a relaxed Old Florida setting. With rustic charm, outdoor seating, and live-local energy, it feels like a hidden fish camp in the heart of Sarasota.
Connors Steak & Seafood serves premium steaks and fresh seafood in an upscale, polished setting. It’s a classic steakhouse with a lively, inviting atmosphere and a menu that balances surf-and-turf favorites with refined sides.
A lush bayfront escape in downtown Sarasota, Marie Selby Botanical Gardens is perfect for plant lovers, art fans, and anyone who enjoys peaceful walks among tropical gardens, mangroves, and sweeping water views.
St. Armands Circle is a charming open-air destination known for its upscale shops, dining, and coastal strolls. It’s perfect for visitors who enjoy a lively, walkable atmosphere with a touch of Sarasota elegance.
Dive into a one-of-a-kind aquarium where cutting-edge marine science meets immersive, hands-on exhibits. It’s perfect for families, curious explorers, and anyone who loves ocean life and learning by discovery.
Bayfront Park is a scenic waterfront escape in the heart of Downtown Miami, with bay views, open green spaces, and a lively mix of walking paths, events, and family-friendly fun. It’s especially great for anyone who enjoys relaxing outdoors with a city skyline backdrop.
Step into a grand Sarasota estate where European masterworks, elegant architecture, and lush bayfront grounds come together in one unforgettable visit. It’s especially appealing for art lovers, history fans, and anyone who enjoys a beautiful cultural day out.
Lido Beach is a relaxing seaside escape known for its soft sand, open views, and easygoing atmosphere. It’s a great choice for anyone who wants to swim, sunbathe, or simply unwind by the water.
Nathan Benderson Park is a scenic waterfront escape known for its world-class rowing course, wide-open trails, and peaceful lake views. It’s ideal for active visitors, nature lovers, and families looking for outdoor fun.
Celery Fields is a unique mix of wetlands, wildlife habitat, and flood-control landscape that’s especially loved by birdwatchers. It’s a great fit for anyone who enjoys peaceful walks, scenic views, and spotting hundreds of bird species.
Free cancellation up to 30 days before check-in. 50% refund up to 7 days before. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Sep 12, 2026 | $222 | Not Available |
| Sep 13, 2026 | $222 | Available |
| Sep 14, 2026 | $224 | Available |
| Sep 15, 2026 | $224 | Available |
| Sep 16, 2026 | $222 | Available |
| Sep 17, 2026 | $222 | Available |
| Sep 18, 2026 | $224 | Available |
| Sep 19, 2026 | $224 | Available |
| Sep 20, 2026 | $224 | Available |
| Sep 21, 2026 | $224 | Available |
| Sep 22, 2026 | $224 | Available |
| Sep 23, 2026 | $224 | Available |
| Sep 24, 2026 | $222 | Available |
| Sep 25, 2026 | $224 | Available |
| Sep 26, 2026 | $222 | Available |
| Sep 27, 2026 | $222 | Available |
| Sep 28, 2026 | $224 | Available |
| Sep 29, 2026 | $224 | Available |
| Sep 30, 2026 | $222 | Available |
| Oct 1, 2026 | $224 | Available |
| Oct 2, 2026 | $224 | Available |
| Oct 3, 2026 | $224 | Available |
| Oct 4, 2026 | $224 | Available |
| Oct 5, 2026 | $222 | Available |
| Oct 6, 2026 | $224 | Available |
| Oct 7, 2026 | $224 | Available |
| Oct 8, 2026 | $222 | Available |
| Oct 9, 2026 | $222 | Available |
| Oct 10, 2026 | $224 | Available |
| Oct 11, 2026 | $222 | Available |
| Oct 12, 2026 | $222 | Available |
| Oct 13, 2026 | $222 | Available |
| Oct 14, 2026 | $222 | Available |
| Oct 15, 2026 | $224 | Available |
| Oct 16, 2026 | $224 | Available |
| Oct 17, 2026 | $222 | Available |
| Oct 18, 2026 | $222 | Available |
| Oct 19, 2026 | $224 | Available |
| Oct 20, 2026 | $224 | Available |
| Oct 21, 2026 | $222 | Available |
| Oct 22, 2026 | $224 | Available |
| Oct 23, 2026 | $224 | Available |
| Oct 24, 2026 | $222 | Available |
| Oct 25, 2026 | $222 | Available |
| Oct 26, 2026 | $224 | Available |
| Oct 27, 2026 | $224 | Available |
| Oct 28, 2026 | $222 | Available |
| Oct 29, 2026 | $224 | Available |
| Oct 30, 2026 | $222 | Available |
| Oct 31, 2026 | $222 | Available |
| Nov 1, 2026 | $222 | Available |
| Nov 2, 2026 | $222 | Available |
| Nov 3, 2026 | $224 | Available |
| Nov 4, 2026 | $224 | Available |
| Nov 5, 2026 | $224 | Not Available |
| Nov 6, 2026 | $222 | Not Available |
| Nov 7, 2026 | $224 | Not Available |
| Nov 8, 2026 | $222 | Not Available |
| Nov 9, 2026 | $222 | Available |
| Nov 10, 2026 | $224 | Available |
| Nov 11, 2026 | $224 | Available |
| Nov 12, 2026 | $228 | Available |
| Nov 13, 2026 | $231 | Available |
| Nov 14, 2026 | $230 | Available |
| Nov 15, 2026 | $222 | Available |
| Nov 16, 2026 | $222 | Available |
| Nov 17, 2026 | $222 | Available |
| Nov 18, 2026 | $222 | Available |
| Nov 19, 2026 | $224 | Available |
| Nov 20, 2026 | $231 | Available |
| Nov 21, 2026 | $238 | Available |
| Nov 22, 2026 | $230 | Available |
| Nov 23, 2026 | $235 | Available |
| Nov 24, 2026 | $260 | Not Available |
| Nov 25, 2026 | $272 | Not Available |
| Nov 26, 2026 | $274 | Not Available |
| Nov 27, 2026 | $265 | Not Available |
| Nov 28, 2026 | $259 | Available |
| Nov 29, 2026 | $222 | Available |
| Nov 30, 2026 | $224 | Available |
| Dec 1, 2026 | $224 | Available |
| Dec 2, 2026 | $222 | Available |
| Dec 3, 2026 | $222 | Available |
| Dec 4, 2026 | $224 | Available |
| Dec 5, 2026 | $224 | Available |
| Dec 6, 2026 | $224 | Available |
| Dec 7, 2026 | $222 | Available |
| Dec 8, 2026 | $222 | Available |
| Dec 9, 2026 | $222 | Available |
| Dec 10, 2026 | $224 | Available |
| Dec 11, 2026 | $237 | Available |