Sarasota, Florida

Pineapple Paradise - 13 min to Beach - Fire Pit

3 bedrooms3 beds3 baths8 guestsNew

About the property

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:

  • Full-sized Bed
  • Nightstand and Lamps
  • Mirror

Pineapple Paradise #2
BEDROOM 2:

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

Pineapple Paradise #3
BEDROOM 3:

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

– 3 BATHROOMS –

  • Full Bathroom with Walk-in Shower
  • Ensuite Bathroom with Walk-in Shower
  • Ensuite Bathroom with Walk-in Shower

– 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
  • Queen Size Sleeper Sofa (Pineapple Paradise #3)

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:

  • Full-sized Bed
  • Nightstand and Lamps
  • Mirror

Pineapple Paradise #2
BEDROOM 2:

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

Pineapple Paradise #3
BEDROOM 3:

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

– 3 BATHROOMS –

  • Full Bathroom with Walk-in Shower
  • Ensuite Bathroom with Walk-in Shower
  • Ensuite Bathroom with Walk-in Shower

– 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
  • Queen Size Sleeper Sofa (Pineapple Paradise #3)

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$201Available2
Jul 29, 2026$201Available2
Jul 30, 2026$200Available2
Jul 31, 2026$200Available2
Aug 1, 2026$200Available2
Aug 2, 2026$201Available2
Aug 3, 2026$200Available2
Aug 4, 2026$200Available2
Aug 5, 2026$200Available2
Aug 6, 2026$201Available2
Aug 7, 2026$201Available2
Aug 8, 2026$200Available2
Aug 9, 2026$201Available2
Aug 10, 2026$201Available2
Aug 11, 2026$201Available2
Aug 12, 2026$200Available2
Aug 13, 2026$200Available2
Aug 14, 2026$201Available2
Aug 15, 2026$200Available2
Aug 16, 2026$201Available2
Aug 17, 2026$201Available2
Aug 18, 2026$201Available2
Aug 19, 2026$200Available2
Aug 20, 2026$200Available2
Aug 21, 2026$201Available2
Aug 22, 2026$201Available2
Aug 23, 2026$200Available2
Aug 24, 2026$201Available2
Aug 25, 2026$200Available2
Aug 26, 2026$201Available2
Aug 27, 2026$200Available2
Aug 28, 2026$201Available2
Aug 29, 2026$200Available2
Aug 30, 2026$200Available2
Aug 31, 2026$201Available2
Sep 1, 2026$200Available2
Sep 2, 2026$200Available2
Sep 3, 2026$201Available3
Sep 4, 2026$201Available3
Sep 5, 2026$200Available3
Sep 6, 2026$200Available3
Sep 7, 2026$201Available3
Sep 8, 2026$201Available2
Sep 9, 2026$201Available2
Sep 10, 2026$201Available3
Sep 11, 2026$201Available3
Sep 12, 2026$200Available3
Sep 13, 2026$200Available2
Sep 14, 2026$201Available2
Sep 15, 2026$200Available2
Sep 16, 2026$200Available2
Sep 17, 2026$200Available3
Sep 18, 2026$200Available3
Sep 19, 2026$201Available3
Sep 20, 2026$200Available2
Sep 21, 2026$201Available2
Sep 22, 2026$200Available2
Sep 23, 2026$201Available2
Sep 24, 2026$200Available3
Sep 25, 2026$201Available3
Sep 26, 2026$201Available3
Sep 27, 2026$200Available2
Sep 28, 2026$200Available2
Sep 29, 2026$200Available2
Sep 30, 2026$201Available2
Oct 1, 2026$201Available3
Oct 2, 2026$200Available3
Oct 3, 2026$201Available3
Oct 4, 2026$201Available2
Oct 5, 2026$201Available2
Oct 6, 2026$201Available2
Oct 7, 2026$200Available2
Oct 8, 2026$200Available3
Oct 9, 2026$200Available3
Oct 10, 2026$200Available3
Oct 11, 2026$201Available3
Oct 12, 2026$201Available3
Oct 13, 2026$200Available2
Oct 14, 2026$200Available2
Oct 15, 2026$200Available3
Oct 16, 2026$200Available3
Oct 17, 2026$201Available3
Oct 18, 2026$200Available2
Oct 19, 2026$201Available2
Oct 20, 2026$201Available2
Oct 21, 2026$201Available2
Oct 22, 2026$200Available3
Oct 23, 2026$201Available3
Oct 24, 2026$200Available3
Oct 25, 2026$201Available3
Oct 26, 2026$200Available3

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

Immerse yourself in the sophisticated coastal charm of Sarasota, where cultural treasures and seaside adventures seamlessly align. Stroll the breathtaking waterfront paths at Marie Selby Botanical Gardens Downtown Sarasota or wander nearby Marina Jack to watch the yachts glide along the sparkling bay. A short drive brings you to the upscale boutiques of St. Armands Circle and family-friendly wildlife encounters at Sarasota Jungle Gardens, while premium

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 8 guests.