Sarasota, Florida

Pineapple Paradise - 2 Units - 13 min to Beach

2 bedrooms2 beds2 baths4 guestsNew

About the property

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):

  • Full-sized Bed
  • Nightstand and Lamps
  • Mirror

BEDROOM 2 (Pineapple 2):

  • Full-sized Bed
  • Nightstand and Lamps
  • Mirror
  • Ensuite Bathroom

– 2 BATHROOMS –

  • Full Bathroom with Walk-in Shower (Pineapple 1)
  • Ensuite Bathroom with Walk-in Shower (Pineapple 2)

– CHEF’S KITCHEN –

  • Fully Stocked
  • High-end Appliances
  • Large Refrigerator
  • Ample Cabinetry
  • Coffee Maker: Drip & Keurig

– LIVING ROOM –

  • Smart TV
  • Plush Sofa + Seating
  • Dedicated Workspace
  • Open Floor Plan

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):

  • Full-sized Bed
  • Nightstand and Lamps
  • Mirror

BEDROOM 2 (Pineapple 2):

  • Full-sized Bed
  • Nightstand and Lamps
  • Mirror
  • Ensuite Bathroom

– 2 BATHROOMS –

  • Full Bathroom with Walk-in Shower (Pineapple 1)
  • Ensuite Bathroom with Walk-in Shower (Pineapple 2)

– CHEF’S KITCHEN –

  • Fully Stocked
  • High-end Appliances
  • Large Refrigerator
  • Ample Cabinetry
  • Coffee Maker: Drip & Keurig

– LIVING ROOM –

  • Smart TV
  • Plush Sofa + Seating
  • Dedicated Workspace
  • Open Floor Plan

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 28, 2026$161Available2
Jul 29, 2026$161Available2
Jul 30, 2026$160Available2
Jul 31, 2026$161Available2
Aug 1, 2026$160Available2
Aug 2, 2026$160Available2
Aug 3, 2026$160Available2
Aug 4, 2026$160Available2
Aug 5, 2026$161Available2
Aug 6, 2026$160Available2
Aug 7, 2026$161Available2
Aug 8, 2026$161Available2
Aug 9, 2026$161Available2
Aug 10, 2026$160Available2
Aug 11, 2026$161Available2
Aug 12, 2026$160Available2
Aug 13, 2026$161Available2
Aug 14, 2026$161Available2
Aug 15, 2026$161Available2
Aug 16, 2026$161Available2
Aug 17, 2026$160Available2
Aug 18, 2026$160Available2
Aug 19, 2026$160Available2
Aug 20, 2026$160Available2
Aug 21, 2026$160Available2
Aug 22, 2026$161Available2
Aug 23, 2026$160Available2
Aug 24, 2026$161Available2
Aug 25, 2026$160Available2
Aug 26, 2026$161Available2
Aug 27, 2026$161Available2
Aug 28, 2026$160Available2
Aug 29, 2026$160Available2
Aug 30, 2026$161Available2
Aug 31, 2026$160Available2
Sep 1, 2026$160Available2
Sep 2, 2026$160Available2
Sep 3, 2026$161Available3
Sep 4, 2026$160Available3
Sep 5, 2026$160Available3
Sep 6, 2026$160Available3
Sep 7, 2026$160Available3
Sep 8, 2026$161Available2
Sep 9, 2026$161Available2
Sep 10, 2026$160Available3
Sep 11, 2026$161Available3
Sep 12, 2026$160Available3
Sep 13, 2026$161Available2
Sep 14, 2026$160Available2
Sep 15, 2026$160Available2
Sep 16, 2026$161Available2
Sep 17, 2026$160Available3
Sep 18, 2026$160Available3
Sep 19, 2026$160Available3
Sep 20, 2026$160Available2
Sep 21, 2026$161Available2
Sep 22, 2026$160Available2
Sep 23, 2026$161Available2
Sep 24, 2026$160Available3
Sep 25, 2026$161Available3
Sep 26, 2026$160Available3
Sep 27, 2026$160Available2
Sep 28, 2026$160Available2
Sep 29, 2026$161Available2
Sep 30, 2026$160Available2
Oct 1, 2026$161Available3
Oct 2, 2026$165Available3
Oct 3, 2026$163Available3
Oct 4, 2026$161Available2
Oct 5, 2026$161Available2
Oct 6, 2026$161Available2
Oct 7, 2026$161Available2
Oct 8, 2026$161Available3
Oct 9, 2026$176Available3
Oct 10, 2026$168Available3
Oct 11, 2026$168Available3
Oct 12, 2026$161Available3
Oct 13, 2026$161Available2
Oct 14, 2026$161Available2
Oct 15, 2026$161Available3
Oct 16, 2026$161Available3
Oct 17, 2026$162Available3
Oct 18, 2026$161Available2
Oct 19, 2026$160Available2
Oct 20, 2026$161Available2
Oct 21, 2026$160Available2
Oct 22, 2026$160Available3
Oct 23, 2026$161Available3
Oct 24, 2026$161Available3
Oct 25, 2026$161Available3
Oct 26, 2026$161Available3

Amenities

BBQ Area
Air conditioning
Bed linens
Coffee maker
Cooking basics
Dishes
Dishwasher
Cleaning supplies

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Where you'll be

Sarasota, Florida, 34236, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

Payment processing fee and a 3% booking fee are non refundable upon cancellation.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 4 guests.