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 –
Check-in is at 4pm
Check-out is at 10am
GUEST VERIFICATION:
To ensure a smooth and secure stay, we require the primary guest listed on the reservation to complete a simple screening process within 48 hours of booking confirmation. Please note that your reservation is not confirmed until these steps are completed.
Once verified, and prior to check-in, guests will be asked to sign a Rental Agreement that includes:
The damage waiver covers accidental damage that may occur during your stay. To ensure coverage, all damage must be reported promptly while you’re still at the property. We understand there is normal wear and tear at houses but should anything accidentally break or get stained during your stay please just let us know. Thank you!
Bedroom
1 full bed
Bedroom
1 full bed
Bedroom
1 full bed
Bedroom
1 full bed
Bedroom
1 full bed
Bedroom
1 full bed
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Sarasota, Florida 34236, US
Sarasota, Florida, USFree 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 |
|---|---|---|
| Oct 17, 2026 | $224 | Not Available |
| Oct 18, 2026 | $224 | Available |
| Oct 19, 2026 | $222 | Available |
| Oct 20, 2026 | $222 | Available |
| Oct 21, 2026 | $222 | Available |
| Oct 22, 2026 | $222 | Not Available |
| Oct 23, 2026 | $222 | Available |
| Oct 24, 2026 | $224 | Available |
| Oct 25, 2026 | $222 | Available |
| Oct 26, 2026 | $222 | Available |
| Oct 27, 2026 | $224 | Available |
| Oct 28, 2026 | $224 | Available |
| Oct 29, 2026 | $224 | Available |
| Oct 30, 2026 | $222 | Available |
| Oct 31, 2026 | $224 | Available |
| Nov 1, 2026 | $224 | Available |
| Nov 2, 2026 | $222 | Available |
| Nov 3, 2026 | $222 | Available |
| Nov 4, 2026 | $224 | Available |
| Nov 5, 2026 | $224 | Not Available |
| Nov 6, 2026 | $224 | Not Available |
| Nov 7, 2026 | $222 | Not Available |
| Nov 8, 2026 | $224 | Not Available |
| Nov 9, 2026 | $222 | Available |
| Nov 10, 2026 | $224 | Available |
| Nov 11, 2026 | $224 | Available |
| Nov 12, 2026 | $224 | Available |
| Nov 13, 2026 | $222 | Available |
| Nov 14, 2026 | $222 | Available |
| Nov 15, 2026 | $224 | Available |
| Nov 16, 2026 | $222 | Available |
| Nov 17, 2026 | $224 | Available |
| Nov 18, 2026 | $224 | Available |
| Nov 19, 2026 | $222 | Available |
| Nov 20, 2026 | $224 | Available |
| Nov 21, 2026 | $224 | Available |
| Nov 22, 2026 | $222 | Available |
| Nov 23, 2026 | $224 | Available |
| Nov 24, 2026 | $224 | Not Available |
| Nov 25, 2026 | $229 | Not Available |
| Nov 26, 2026 | $230 | Not Available |
| Nov 27, 2026 | $227 | Not Available |
| Nov 28, 2026 | $224 | Available |
| Nov 29, 2026 | $224 | Available |
| Nov 30, 2026 | $224 | Available |
| Dec 1, 2026 | $222 | Available |
| Dec 2, 2026 | $222 | Available |
| Dec 3, 2026 | $222 | Available |
| Dec 4, 2026 | $222 | Available |
| Dec 5, 2026 | $224 | Available |
| Dec 6, 2026 | $222 | Available |
| Dec 7, 2026 | $222 | Available |
| Dec 8, 2026 | $224 | Available |
| Dec 9, 2026 | $224 | Available |
| Dec 10, 2026 | $222 | Available |
| Dec 11, 2026 | $222 | Available |
| Dec 12, 2026 | $224 | Available |
| Dec 13, 2026 | $222 | Available |
| Dec 14, 2026 | $224 | Available |
| Dec 15, 2026 | $222 | Available |
| Dec 16, 2026 | $222 | Available |
| Dec 17, 2026 | $224 | Available |
| Dec 18, 2026 | $234 | Available |
| Dec 19, 2026 | $259 | Available |
| Dec 20, 2026 | $265 | Available |
| Dec 21, 2026 | $294 | Available |
| Dec 22, 2026 | $298 | Available |
| Dec 23, 2026 | $346 | Available |
| Dec 24, 2026 | $365 | Available |
| Dec 25, 2026 | $387 | Available |
| Dec 26, 2026 | $396 | Available |
| Dec 27, 2026 | $406 | Available |
| Dec 28, 2026 | $415 | Available |
| Dec 29, 2026 | $416 | Available |
| Dec 30, 2026 | $375 | Available |
| Dec 31, 2026 | $378 | Available |
| Jan 1, 2027 | $382 | Available |
| Jan 2, 2027 | $365 | Available |
| Jan 3, 2027 | $302 | Available |
| Jan 4, 2027 | $269 | Available |
| Jan 5, 2027 | $265 | Available |
| Jan 6, 2027 | $270 | Available |
| Jan 7, 2027 | $287 | Available |
| Jan 8, 2027 | $310 | Available |
| Jan 9, 2027 | $311 | Available |
| Jan 10, 2027 | $291 | Available |
| Jan 11, 2027 | $265 | Available |
| Jan 12, 2027 | $226 | Available |
| Jan 13, 2027 | $232 | Available |
| Jan 14, 2027 | $310 | Not Available |
| Jan 15, 2027 | $348 | Not Available |