Sarasota, FL

The Pearl on the Bay - 1370

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8 guests
4 bedrooms
4 bathrooms
3506 sqft

Escape to Paradise at The Pearl on the Bay

8 guests
4 bedrooms
4 bathrooms
3506 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation

    You can cancel your trip for up to 14 days prior to start.


About this property

Escape to Paradise at The Pearl on the Bay Indulge in the ultimate waterfront escape at The Pearl on the Bay, a breathtaking residence nestled in the prestigious San Remo neighborhood of Siesta Key. This exquisite home offers unparalleled luxury and stunning views, creating the perfect backdrop for an unforgettable vacation. Unparalleled Luxury and Waterfront Views: Prime Location: Enjoy breathtaking water views and easy access to the Intracoastal Waterway from this prestigious San Remo neighborhood. Luxurious Amenities: Immerse yourself in the luxurious amenities, including a private heated pool and spa, a fishing dock with underwater lights, and a spacious covered deck with a fire table. Elegant Interiors: The interior boasts elegant design with five HD smart TVs, a chef's kitchen featuring Wolf and Subzero appliances, and four spacious master bedrooms, each with a king or queen bed. Unforgettable Experiences: Waterfront Adventures: Explore the nearby waters with the provided kayak and paddleboards, or try your luck at fishing from the dock. Relaxation and Recreation: Lounge poolside, soak in the spa, or unwind on the hammock while enjoying the captivating scenery. Gourmet Dining: Prepare delicious meals in the fully equipped kitchen or dine al fresco on the outdoor patio. A Home Away From Home: Comfort and Convenience: Enjoy the convenience of free Wi-Fi, a starter pack of toiletries and home essentials, and comfortable linens. Privacy and Relaxation: Each of the four master bedrooms offers a peaceful retreat for ultimate relaxation. Book Your Waterfront Getaway Today! Exclusive Amenities Include: • Private Heated Pool & Spa • Breathtaking Intracoastal Views • 4 Bedrooms (4 Master Bedrooms), 4 Full Baths • 3 King Beds, 1 Queen Beds (Sleeps 8) with linens provided • Outdoor Dining Space • Fishing Dock w/ Underwater Lights • Outdoor Fire Table • Spacious Balcony Deck Viewing The Bay w/ Lounging & Exterior Dinning Areas • Private 2 Car Garage • Free WiFi & 5 HD Smart TV's • Wolf / Subzero Kitchen Appliances, Regular & Keurig Coffee Maker, Washer and Dryer Set, and Kitchen Essentials Provided • Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes • Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes • Beach Towels, Chairs, Cooler, & Caddy Provided • Outdoor Lounge Area Includes Private Heated Pool, Spa, Fire Table, Hammocks, Crows Nest, Gas Grill, & more • 1 Kayak & 2 Paddle Boards • Enhanced cleaning protocols provided by our CottageClean Team • Island Shuttle Transportation Available The Pearl on The Bay can accommodate up to 10 guests with a bedding configuration as follows: •Bedroom #1: King Bed (1) - sleeps: 2 •Bedroom #2: King Bed (1) - sleeps: 2 •Bedroom #3: King Bed (1) - sleeps: 2 •Bedroom #4: Queen beds (1) - sleeps: 2 PLEASE NOTE: This pool is heated from November 15th to April 15th.

Escape to Paradise at The Pearl on the Bay Indulge in the ultimate waterfront escape at The Pearl on the Bay, a breathtaking residence nestled in the prestigious San Remo neighborhood of Siesta Key. This exquisite home offers unparalleled luxury and stunning views, creating the perfect backdrop for an unforgettable vacation. Unparalleled Luxury and Waterfront Views: Prime Location: Enjoy breathtaking water views and easy access to the Intracoastal Waterway from this prestigious San Remo neighborhood. Luxurious Amenities: Immerse yourself in the luxurious amenities, including a private heated pool and spa, a fishing dock with underwater lights, and a spacious covered deck with a fire table. Elegant Interiors: The interior boasts elegant design with five HD smart TVs, a chef's kitchen featuring Wolf and Subzero appliances, and four spacious master bedrooms, each with a king or queen bed. Unforgettable Experiences: Waterfront Adventures: Explore the nearby waters with the provided kayak and paddleboards, or try your luck at fishing from the dock. Relaxation and Recreation: Lounge poolside, soak in the spa, or unwind on the hammock while enjoying the captivating scenery. Gourmet Dining: Prepare delicious meals in the fully equipped kitchen or dine al fresco on the outdoor patio. A Home Away From Home: Comfort and Convenience: Enjoy the convenience of free Wi-Fi, a starter pack of toiletries and home essentials, and comfortable linens. Privacy and Relaxation: Each of the four master bedrooms offers a peaceful retreat for ultimate relaxation. Book Your Waterfront Getaway Today! Exclusive Amenities Include: • Private Heated Pool & Spa • Breathtaking Intracoastal Views • 4 Bedrooms (4 Master Bedrooms), 4 Full Baths • 3 King Beds, 1 Queen Beds (Sleeps 8) with linens provided • Outdoor Dining Space • Fishing Dock w/ Underwater Lights • Outdoor Fire Table • Spacious Balcony Deck Viewing The Bay w/ Lounging & Exterior Dinning Areas • Private 2 Car Garage • Free WiFi & 5 HD Smart TV's • Wolf / Subzero Kitchen Appliances, Regular & Keurig Coffee Maker, Washer and Dryer Set, and Kitchen Essentials Provided • Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes • Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes • Beach Towels, Chairs, Cooler, & Caddy Provided • Outdoor Lounge Area Includes Private Heated Pool, Spa, Fire Table, Hammocks, Crows Nest, Gas Grill, & more • 1 Kayak & 2 Paddle Boards • Enhanced cleaning protocols provided by our CottageClean Team • Island Shuttle Transportation Available The Pearl on The Bay can accommodate up to 10 guests with a bedding configuration as follows: •Bedroom #1: King Bed (1) - sleeps: 2 •Bedroom #2: King Bed (1) - sleeps: 2 •Bedroom #3: King Bed (1) - sleeps: 2 •Bedroom #4: Queen beds (1) - sleeps: 2 PLEASE NOTE: This pool is heated from November 15th to April 15th.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Dec 11, 2025$721.28Available2
Dec 12, 2025$715.39Not Available3
Dec 13, 2025$709.50Not Available2
Dec 14, 2025$709.50Not Available3
Dec 15, 2025$709.50Not Available3
Dec 16, 2025$709.50Not Available3
Dec 17, 2025$721.28Not Available3
Dec 18, 2025$1,137.18Not Available3
Dec 19, 2025$1,568.20Not Available3
Dec 20, 2025$2,017.67Not Available3
Dec 21, 2025N/ANot Available3
Dec 22, 2025N/ANot Available3
Dec 23, 2025N/ANot Available3
Dec 24, 2025N/ANot Available3
Dec 25, 2025N/ANot Available3
Dec 26, 2025N/ANot Available3
Dec 27, 2025$3,060.68Not Available3
Dec 28, 2025N/ANot Available3
Dec 29, 2025N/ANot Available3
Dec 30, 2025N/ANot Available3
Dec 31, 2025N/ANot Available3
Jan 1, 2026N/ANot Available3
Jan 2, 2026N/ANot Available3
Jan 3, 2026$864.72Available3
Jan 4, 2026$851.76Available3
Jan 5, 2026$845.27Available3
Jan 6, 2026$838.79Available3
Jan 7, 2026$845.27Available3
Jan 8, 2026$851.76Available3
Jan 9, 2026$858.24Available3
Jan 10, 2026$858.24Not Available3
Jan 11, 2026$858.24Not Available3
Jan 12, 2026$858.24Not Available3
Jan 13, 2026$864.72Not Available3
Jan 14, 2026$871.19Not Available3
Jan 15, 2026$1,029.14Not Available3
Jan 16, 2026$1,170.99Not Available3
Jan 17, 2026$1,332.09Available2
Jan 18, 2026$1,332.09Available2
Jan 19, 2026$1,341.71Available2
Jan 20, 2026$1,341.71Not Available3
Jan 21, 2026$1,351.34Not Available3
Jan 22, 2026$1,360.97Not Available3
Jan 23, 2026$1,360.97Not Available3
Jan 24, 2026$1,370.59Not Available3
Jan 25, 2026$1,380.21Not Available3
Jan 26, 2026$1,389.83Not Available3
Jan 27, 2026$1,399.45Not Available3
Jan 28, 2026$1,409.07Not Available3
Jan 29, 2026$1,497.25Not Available3
Jan 30, 2026$1,586.80Not Available3
Jan 31, 2026$1,687.35Not Available3
Feb 1, 2026$1,709.34Not Available3
Feb 2, 2026$1,720.34Not Available2
Feb 3, 2026$1,720.34Not Available3
Feb 4, 2026$1,731.34Not Available3
Feb 5, 2026$1,742.33Not Available3
Feb 6, 2026$1,764.33Not Available3
Feb 7, 2026$1,786.33Not Available3
Feb 8, 2026N/ANot Available3
Feb 9, 2026N/ANot Available3
Feb 10, 2026N/ANot Available3
Feb 11, 2026N/ANot Available3
Feb 12, 2026N/ANot Available3
Feb 13, 2026N/ANot Available3
Feb 14, 2026$2,710.14Not Available3
Feb 15, 2026N/ANot Available3
Feb 16, 2026N/ANot Available3
Feb 17, 2026N/ANot Available3
Feb 18, 2026N/ANot Available3
Feb 19, 2026N/ANot Available3
Feb 20, 2026N/ANot Available3
Feb 21, 2026$3,152.98Not Available3
Feb 22, 2026$3,188.72Not Available3
Feb 23, 2026$3,206.59Not Available3
Feb 24, 2026$3,188.73Not Available3
Feb 25, 2026$3,152.99Not Available3
Feb 26, 2026$3,313.63Not Available3
Feb 27, 2026$3,452.96Not Available2
Feb 28, 2026$3,652.79Not Available3
Mar 1, 2026N/ANot Available3
Mar 2, 2026N/ANot Available3
Mar 3, 2026N/ANot Available3
Mar 4, 2026N/ANot Available3
Mar 5, 2026N/ANot Available3
Mar 6, 2026N/ANot Available3
Mar 7, 2026$3,588.86Not Available3
Mar 8, 2026N/ANot Available3
Mar 9, 2026N/ANot Available3
Mar 10, 2026N/ANot Available3
Mar 11, 2026N/ANot Available3

Amenities

Carbon monoxide detector
Air conditioning
Balcony
BBQ Area
Beach essentials
Balcony
BBQ Area
BBQ Utensils
Air conditioning

Where you'll sleep



Explore Sarasota, FL

Set in the upscale San Remo neighborhood near Siesta Key, Florida, this home sits right on the Intracoastal Waterway offering uninterrupted views and access to the bay. With direct water frontage and easy reach to beachfront dining, boutique shopping, and the Gulf of Mexico, the location brings together serene luxury and coastal lifestyle.

Things to know

Here are some things which you should know before booking The Pearl on the Bay - 1370

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
8 guests maximum
Pets not allowed
Events require approval

Cancellation policy

This property follows Vaaraway’s standard cancellation policy.