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

5.0/10
  • Waterfront
  • Hot tub
  • Kayaks
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


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)
Feb 18, 2026N/ANot Available3
Feb 19, 2026N/ANot Available3
Feb 20, 2026N/ANot Available3
Feb 21, 2026$2,795.55Not Available3
Feb 22, 2026$2,795.55Not Available3
Feb 23, 2026$2,795.55Not Available3
Feb 24, 2026$2,813.42Not Available3
Feb 25, 2026$2,831.30Not Available3
Feb 26, 2026$3,010.50Not Available3
Feb 27, 2026$3,150.52Not Available2
Feb 28, 2026$3,311.86Not 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$3,290.54Not Available3
Mar 8, 2026N/ANot Available3
Mar 9, 2026N/ANot Available3
Mar 10, 2026N/ANot Available3
Mar 11, 2026N/ANot Available3
Mar 12, 2026N/ANot Available3
Mar 13, 2026N/ANot Available3
Mar 14, 2026$3,354.48Not Available3
Mar 15, 2026N/ANot Available3
Mar 16, 2026N/ANot Available3
Mar 17, 2026N/ANot Available3
Mar 18, 2026N/ANot Available3
Mar 19, 2026N/ANot Available3
Mar 20, 2026N/ANot Available3
Mar 21, 2026$3,122.55Not Available2
Mar 22, 2026N/ANot Available3
Mar 23, 2026N/ANot Available3
Mar 24, 2026N/ANot Available3
Mar 25, 2026N/ANot Available3
Mar 26, 2026N/ANot Available3
Mar 27, 2026N/ANot Available3
Mar 28, 2026$3,570.90Not Available3
Mar 29, 2026N/ANot Available3
Mar 30, 2026N/ANot Available3
Mar 31, 2026N/ANot Available3
Apr 1, 2026N/ANot Available3
Apr 2, 2026N/ANot Available3
Apr 3, 2026N/ANot Available3
Apr 4, 2026$2,972.11Not Available2
Apr 5, 2026N/ANot Available3
Apr 6, 2026N/ANot Available3
Apr 7, 2026N/ANot Available3
Apr 8, 2026N/ANot Available3
Apr 9, 2026N/ANot Available3
Apr 10, 2026N/ANot Available3
Apr 11, 2026$1,751.64Not Available2
Apr 12, 2026N/ANot Available3
Apr 13, 2026N/ANot Available3
Apr 14, 2026N/ANot Available3
Apr 15, 2026N/ANot Available3
Apr 16, 2026N/ANot Available3
Apr 17, 2026N/ANot Available3
Apr 18, 2026$1,592.40Not Available2
Apr 19, 2026N/ANot Available3
Apr 20, 2026N/ANot Available3
Apr 21, 2026N/ANot Available3
Apr 22, 2026N/ANot Available3
Apr 23, 2026N/ANot Available3
Apr 24, 2026N/ANot Available3
Apr 25, 2026$1,603.21Not Available2
Apr 26, 2026N/ANot Available3
Apr 27, 2026N/ANot Available3
Apr 28, 2026N/ANot Available3
Apr 29, 2026N/ANot Available3
Apr 30, 2026N/ANot Available3
May 1, 2026$1,292.29Not Available2
May 2, 2026$1,122.24Not Available3
May 3, 2026N/ANot Available3
May 4, 2026N/ANot Available3
May 5, 2026N/ANot Available3
May 6, 2026N/ANot Available3
May 7, 2026N/ANot Available3
May 8, 2026N/ANot Available3
May 9, 2026$1,137.36Not Available3
May 10, 2026N/ANot Available3
May 11, 2026N/ANot Available3
May 12, 2026N/ANot Available3
May 13, 2026N/ANot Available3
May 14, 2026N/ANot Available3
May 15, 2026N/ANot Available3
May 16, 2026$1,182.74Not Available2
May 17, 2026N/ANot Available3
May 18, 2026N/ANot Available3
May 19, 2026N/ANot Available3

Amenities

Waterfront
Hot tub
Fire pit
Fire place
BBQ Area
Patio
Balcony
Kayaks
Carbon monoxide detector

Where you'll sleep



5.0 Guest love this place

8 VERIFIED REVIEWS
5.0 / 5
"Our stay at Roberts Bay was magical! Every morning we saw Roseate Spoonbills, dolphins, and fish right from the property. We loved the ‘indoor-outdoor’ feel with the bifold doors open. The house was beautiful, well-stocked for cooking, and perfectly set up for families.<br/>We stayed busy swimming in the pool, relaxing in the spa, and playing basketball. A highlight was using the provided canoes and paddleboards for nature excursions; my son loved taking the canoe to find hidden fishing spots! Evenings were spent playing board games, watching movies on the big screen, or enjoying breathtaking sunsets by the fire pit.<br/>The host was incredibly hospitable and came by personally to help with any questions. We had such a memorable experience and will definitely be back!
Lucienne
LucienneStayed in February 2026
5.0 / 5
A wonderful home in a wonderful neighborhood, we always base our experience on whether or not we would rent again and when I asked my wife it was an immediate yes and I had to agree. Hard to believe how quiet and peaceful this home is at night. Also sitting and watching the intercoastal boat traffic was a great morning coffee activity, with access to a great waterway to endless possibilities was perfect (Midnight Pass was amazing with a little closer boat ride to Lido Beach was also beautiful) We also brought our own paddle boards and combined the provided ones as well for several nice adventures. This home has a great feel, and we felt right at home which is super important to us as we love our home and hate to leave so we have high expectations. This place checked all of the boxes for our family, thank you so much!
Chris
ChrisStayed in November 2025
5.0 / 5
Beautiful home in an even more beautiful setting and location. So close to Siesta as well as downtown Sarasota. Would definitely consider booking this house again; our only slight issues would be the master bathroom shower being hard to use (confusing configuration) and the house nextdoor coming on the market while we were there so there was TONS of traffic going in and out of the house and people walking the backyard area the whole time. Other than that it was excellent
Brandyn
BrandynStayed in November 2025
5.0 / 5
Such a Beautiful Spot. ☝🏾Of my Favorites 🐦☀️☀️☀️☀️🙏🏾💙💗💜🌈
Geoanna
GeoannaStayed in November 2025
5.0 / 5
Beautiful, tasteful, home, inside and outside. Everything was superb: furnishings, beds, pool, and the prime location...will definitely return!
Kathy
KathyStayed in November 2025
5.0 / 5
The property was even better than the photos display. Phenomenal views from almost every location of the house!! I would recommend this property for anyone who needs a nice relaxing get away.
John
JohnStayed in November 2025

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 allowed with fee (max 2)
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Vaaraway’s standard cancellation policy.