2 bedrooms
•
2 beds
•
2 bathrooms
•
4 guests
•
New
•
1194.7929 sq. ft.
Operated by a Wander partner
Trusted operators, vetted by Wander
Escape to sunny Sarasota with this one-of-a-kind 2-unit retreat, perfect for families, friends, or multi-generational travelers! Rent both 2-bedroom units for extra space, enjoy flexible accommodations, and experience the ultimate vacation filled with relaxation, fun, and memorable moments together.
• 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 - 2 cars
Welcome to Pineapple 1 & 2, a charming combo listing in the heart of Sarasota—ideal for couples, friends, or a small family traveling together while still enjoying a bit of privacy. This thoughtfully designed retreat offers 2 bedrooms and 2 full bathrooms, comfortably accommodating up to 4 guests. Each unit features a cozy coastal vibe and all the essentials for a relaxing, effortless stay.
Located just minutes from downtown Sarasota, you’ll be close to beautiful Gulf beaches, top dining spots, shopping, and the area’s vibrant arts and culture scene. Whether you’re soaking up the sun, exploring the city, or unwinding after a beach day, Pineapple 1 & 2 is the perfect home base. Experience the best of Sarasota—comfort, convenience, and coastal charm all in one place!
MAIN SPACES OF THE HOME:
– 2 BEDROOMS & 2 BATHROOMS –
BEDROOM 1 (Pineapple 1):
BEDROOM 2 (Pineapple 2):
– 2 BATHROOMS –
– CHEF’S KITCHEN –
– LIVING ROOM –
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, USWalt’s Fish Market is a laid-back Sarasota seafood spot serving exceptionally fresh, catch-of-the-day fish from its own working market. With a tiki bar and no-frills coastal vibe, it feels both local and distinctly Florida.
Dry Dock Waterfront Grill serves fresh seafood in a casual waterfront setting with panoramic Sarasota Bay views. It’s especially known for its grouper sandwich and relaxed dockside ambiance.
Der Dutchman serves hearty Amish-inspired comfort food in a warm, rustic setting. It’s known for generous buffet-style dining, homestyle baked goods, and a welcoming, family-friendly atmosphere.
Marina Jack is a beloved Sarasota waterfront restaurant serving seafood and American fare with sweeping bay views. Its mix of fine dining, patio seating, and live music creates an upbeat, scenic dining experience.
St. Armands Circle offers a lively mix of Mediterranean, Italian, Cuban, and seafood dining, all set in a charming, upscale outdoor shopping district. Many spots feature stylish patios and a relaxed, vacation-like atmosphere.
Yoder’s Restaurant serves hearty Amish comfort food, from homemade baked goods to award-winning pies, in a friendly, down-home setting. It’s a longtime local favorite known for simple, satisfying meals and warm hospitality.
Lido Beach is a laid-back stretch of soft sand and calm water, perfect for swimming, sunset walks, and easygoing beach days. It’s especially appealing to families, couples, and anyone who enjoys a scenic spot with a relaxed local feel.
Bayfront Park is a lively waterfront escape in downtown Miami, known for its Biscayne Bay views, open lawns, and year-round events. It’s especially great for families, walkers, and anyone who enjoys relaxing outdoors with a city skyline backdrop.
Mote SEA is a stunning, hands-on aquarium where marine science comes to life through immersive habitats and interactive exhibits. It’s ideal for families, curious kids, and anyone who loves ocean life and discovery.
A lush bayfront escape in downtown Sarasota, Marie Selby Botanical Gardens blends tropical plants, artful displays, and scenic mangrove walks. It’s ideal for nature lovers, photographers, and anyone seeking a peaceful, beautiful outing.
Celery Fields is a scenic Sarasota wetland preserve known for exceptional birdwatching, peaceful trails, and wide-open views. It’s especially great for nature lovers, walkers, cyclists, and anyone looking for a quiet outdoor escape.
The John and Mable Ringling Museum of Art blends world-class European art with stunning architecture and bayfront gardens, making it a memorable stop for art lovers, history buffs, and anyone who enjoys beautiful, one-of-a-kind places.
Sarasota Jungle Gardens is a lush Old Florida escape where families can wander tropical trails and enjoy entertaining wildlife shows. It’s especially appealing to animal lovers, kids, and anyone who enjoys a relaxed, nostalgic outing.
Nathan Benderson Park is a scenic waterfront destination with a world-class rowing course, perfect for active visitors who enjoy kayaking, biking, walking, and outdoor events. Families, fitness fans, and nature lovers will all find plenty to enjoy here.
St. Armands Circle is a charming, walkable mix of boutiques, galleries, and restaurants set in a stylish European-inspired plaza near the beach. It’s perfect for anyone who enjoys shopping, dining, and an easygoing coastal stroll.
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
4 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 28, 2026 | $178 | Not Available |
| Jul 29, 2026 | $179 | Available |
| Jul 30, 2026 | $178 | Available |
| Jul 31, 2026 | $178 | Available |
| Aug 1, 2026 | $178 | Available |
| Aug 2, 2026 | $179 | Available |
| Aug 3, 2026 | $179 | Available |
| Aug 4, 2026 | $179 | Available |
| Aug 5, 2026 | $179 | Available |
| Aug 6, 2026 | $178 | Available |
| Aug 7, 2026 | $179 | Available |
| Aug 8, 2026 | $178 | Available |
| Aug 9, 2026 | $179 | Available |
| Aug 10, 2026 | $178 | Available |
| Aug 11, 2026 | $178 | Available |
| Aug 12, 2026 | $178 | Available |
| Aug 13, 2026 | $179 | Available |
| Aug 14, 2026 | $179 | Available |
| Aug 15, 2026 | $179 | Available |
| Aug 16, 2026 | $179 | Available |
| Aug 17, 2026 | $178 | Available |
| Aug 18, 2026 | $178 | Available |
| Aug 19, 2026 | $179 | Available |
| Aug 20, 2026 | $179 | Available |
| Aug 21, 2026 | $178 | Available |
| Aug 22, 2026 | $178 | Available |
| Aug 23, 2026 | $178 | Available |
| Aug 24, 2026 | $178 | Available |
| Aug 25, 2026 | $179 | Available |
| Aug 26, 2026 | $179 | Available |
| Aug 27, 2026 | $178 | Available |
| Aug 28, 2026 | $179 | Available |
| Aug 29, 2026 | $178 | Available |
| Aug 30, 2026 | $179 | Available |
| Aug 31, 2026 | $179 | Available |
| Sep 1, 2026 | $179 | Available |
| Sep 2, 2026 | $179 | Available |
| Sep 3, 2026 | $179 | Available |
| Sep 4, 2026 | $179 | Available |
| Sep 5, 2026 | $178 | Available |
| Sep 6, 2026 | $178 | Available |
| Sep 7, 2026 | $178 | Available |
| Sep 8, 2026 | $178 | Available |
| Sep 9, 2026 | $178 | Available |
| Sep 10, 2026 | $179 | Available |
| Sep 11, 2026 | $178 | Available |
| Sep 12, 2026 | $178 | Available |
| Sep 13, 2026 | $179 | Available |
| Sep 14, 2026 | $178 | Available |
| Sep 15, 2026 | $178 | Available |
| Sep 16, 2026 | $179 | Available |
| Sep 17, 2026 | $178 | Available |
| Sep 18, 2026 | $179 | Available |
| Sep 19, 2026 | $178 | Available |
| Sep 20, 2026 | $179 | Available |
| Sep 21, 2026 | $179 | Available |
| Sep 22, 2026 | $178 | Available |
| Sep 23, 2026 | $178 | Available |
| Sep 24, 2026 | $178 | Available |
| Sep 25, 2026 | $179 | Available |
| Sep 26, 2026 | $179 | Available |
| Sep 27, 2026 | $179 | Available |
| Sep 28, 2026 | $178 | Available |
| Sep 29, 2026 | $179 | Available |
| Sep 30, 2026 | $179 | Available |
| Oct 1, 2026 | $178 | Available |
| Oct 2, 2026 | $184 | Available |
| Oct 3, 2026 | $180 | Available |
| Oct 4, 2026 | $178 | Available |
| Oct 5, 2026 | $178 | Available |
| Oct 6, 2026 | $178 | Available |
| Oct 7, 2026 | $178 | Available |
| Oct 8, 2026 | $180 | Available |
| Oct 9, 2026 | $195 | Available |
| Oct 10, 2026 | $187 | Available |
| Oct 11, 2026 | $184 | Available |
| Oct 12, 2026 | $179 | Available |
| Oct 13, 2026 | $179 | Available |
| Oct 14, 2026 | $179 | Available |
| Oct 15, 2026 | $178 | Available |
| Oct 16, 2026 | $178 | Available |
| Oct 17, 2026 | $178 | Available |
| Oct 18, 2026 | $178 | Available |
| Oct 19, 2026 | $179 | Available |
| Oct 20, 2026 | $179 | Available |
| Oct 21, 2026 | $178 | Available |
| Oct 22, 2026 | $179 | Available |
| Oct 23, 2026 | $178 | Available |
| Oct 24, 2026 | $178 | Available |
| Oct 25, 2026 | $178 | Available |
| Oct 26, 2026 | $179 | Available |