Step into serenity as you dip into your private waterfront pool—palm trees swaying, spa bubbles rising, and the waterway sparkling just beyond. Water everywhere you look—this is life at the edge of paradise, nestled in San Remo’s most exclusive corner. Bird’s eye of The Pearl on the Bay—your private retreat framed by tropical palms, with direct access to the shimmering intracoastal. Feel the warmth of the setting sun reflect off the still waters as you float in the private pool, where the bay stretches endlessly beyond—pure serenity with a golden-hour glow. Sink into the patio lounge as the fire pit flickers, the pool glistens, and the sun melts into the bay—this is your front-row seat to paradise. Float above it all—your private dock, shimmering pool, and elegant waterfront home await, nestled perfectly on the edge of the bay. Second floor balcony where lounge chairs line the sun-drenched deck, your favorite drink in hand and not a care in the world. Gaze down on your private slice of Siesta Key paradise—where the elegant bayfront home, sparkling pool, and tranquil waters come together in one unforgettable view. Curb appeal with coastal elegance—the Pearl welcomes you with a wide driveway, tropical landscaping, and architectural grace. Step onto the charming front deck and through the vibrant red door—your luxurious waterfront retreat begins the moment you arrive. Chef’s dream kitchen, where Wolf and Sub-Zero meet morning mimosas and candlelit dinner prep. Wolf range, Sub-Zero fridge, fully stocked—every inch curated for those who know and love to cook. Feel the smooth, cool surface beneath your hands as you prep fresh local seafood, ready to savor with stunning bay views just beyond the window. Sip your morning coffee here as warm sunlight spills in, the perfect spot to start your day with peaceful bay breezes and a gentle hum of waves nearby. Soft evening light wraps the breakfast bar and dining table, inviting you to savor intimate meals while the sunset casts a golden glow through the windows. Kitchen island perfect for wine and appetizers, with high-end finishes that make cooking feel indulgent. An inviting space where the breakfast bar and dining table blend seamlessly with the cozy living room beyond—perfect for sharing stories, laughter, and sunset views all under one roof. Sunlight spills across the breakfast bar and dining table, inviting you to savor morning coffee or evening meals while soaking in the relaxed flow toward the living area. The dining table takes center stage—perfect for sharing meals, laughter, and sunset views through the wide open living space beyond. Gather at the dining table with water as your backdrop, where every meal feels like a celebration. Double sliders blur indoor-outdoor living, inviting salty air and conversation to flow freely. Sink into plush seating beside the sleek fireplace, where warm flames meet cool coastal vibes and the bay glows just beyond the glass. Sink into plush seating in the living room, where calming tones and soft light invite you to fully unwind. From cozy couches to sunset-soaked sliders, this expansive living space flows effortlessly—welcoming you into the heart of waterfront living. Feel the warmth of the setting sun wash over you while lounging in total comfort—just steps from the breezy bayfront deck. Living room opens to water views with sunset reflections dancing off the bay. The fire crackles, the sky blushes, and through the sliders, the view stretches wide—pure waterfront magic from the heart of the home. Gaze through four massive glass sliders to a glowing balcony and a bay kissed by sunset—where every evening feels like a private show. Sink into plush seating as golden sunlight spills across the room—just beyond, the bay shimmers through wall-to-wall glass, drawing you into the view. Bedroom I, a king suite with plush bedding and private bath access, every detail tailored for deep rest. This king suite features peaceful garden views, perfect for couples or those seeking quiet comfort. Step into your private ensuite where a sleek sink and glass-enclosed shower offer a refreshing start or a calming close to your day. Unwind in a space designed for ease and elegance—featuring a spacious vanity with a lighted mirror and a glass-enclosed shower just steps away. Spa-like ensuite with a spacious vanity and a glass shower featuring a built-in bench—your perfect spot to relax and refresh. Bedroom 2, stretch out on the plush king bed or curl up in the cozy chair and ottoman—your private retreat after a day by the bay. Sink into the king bed while your favorite show plays on the wall-mounted TV, creating the perfect blend of comfort and entertainment. Step into your private spa-like bathroom where warm light wraps around the sleek vanity and glass shower, inviting you to refresh and unwind. Breathe in the salty breeze as you sink into the cozy outdoor seating, soaking up the sparkling bay views and warm midday sun. Lounge seating by the water, soft cushions and a breeze scented with salt and sunshine. Twilight reflections on the bay, as the sun sets and your evening begins. Sway gently in the hammock as golden sunset hues dance across the bay, wrapping you in pure tranquility and bliss. Grill station just steps from the kitchen, with easy flow to the dining area and pool beyond. Twilight softens the sky as you dine al fresco, the warm glow from inside inviting you to savor every moment overlooking the shimmering bay. Bayfront balcony dining, fresh catch grilling nearby, laughter echoing into the night. Bedroom 4, with water views, and private sliders to the patio—your sanctuary awaits. Spacious and serene, Bedroom 4 welcomes you with soothing tones and ample natural light for a restful escape. Bright and elegant, the ensuite bathroom offers a sleek glass shower and modern fixtures that invite you to unwind in style. ChatGPT said: Curl up on the plush sofa or chair in Bedroom 4’s cozy living area, your private nook to unwind. A spacious retreat: Bedroom 4’s living area opens up to a TV and plenty of room to relax in style. The home’s stunning façade glows warmly against the twilight sky, inviting you inside to unforgettable evenings. Up close, the twilight casts a magical glow over the elegant entrance, setting the tone for a luxurious stay. The glowing warmth from inside spills out into the twilight, promising cozy nights and peaceful moments overlooking the tranquil backyard. The Pearl glows at dusk, firelight flickering, pool shimmering, and the house wrapped in quiet luxury. Soak in the spa, toes in warm water, with unobstructed views across the calm intracoastal—pure Siesta Key magic. Evening glow, underwater light show—watch the bay light up while the pool glows from within, inviting one more sunset soak.

The Pearl on the Bay – 1370

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Overview Amenities Availability Location Room Details Reviews

Description

The Pearl on the Bay Bayfront Luxury Retreat | Heated Pool, Spa, Fire Table, Sunsets Water Access

Why You ll Love This Home

Wake up to sweeping water views over Roberts Bay, then unwind with cocktails on the west-facing deck as the sun melts into the horizon. This Beachy Lux single-family home pairs refined interiors with outdoor living that feels like a private resort.

Every corner invites ease, from the chef-ready kitchen to the heated pool, spa, and fire table under the stars, perfect for shared moments and lifelong memories.

Perfect For

Families, couples, multigenerational groups, luxury travelers, and water lovers seeking stylish space and direct bay access.

️ Imagine This

Step inside and feel the calm of coastal living: gentle breezes drift in while light plays off the water. Mornings begin with espresso from your Keurig or regular brewer before a dip in the heated pool.

In the afternoon, launch the provided kayak or paddleboards straight from your private dock, or savor sunset from the spa as the sky bursts into color over the bay. Evenings gather around the fire table with laughter, then retreat to plush master suites overlooking water that glimmers under moonlight.

Where You ll Sleep

Primary Bedroom: King Bed, Ensuite Bath, Bay Views

Second Bedroom: King Bed, Shared Bath, TV

Third Bedroom: King Bed, Shared Bath, TV

Fourth Bedroom: Queen Bed, Shared Bath, TV

Explore the Area

4.6 Miles to Siesta Public Beach World-famous quartz-white sand, turquoise Gulf waters, and full beach amenities

4.4 Miles to Siesta Key Village Dining, shopping, nightlife trolley access

3.5 Downtown Sarasota – a lively mix of culture, dining, shopping, and outdoor recreation

3.9 Miles to Bayfront Park Bayfront dining, sunset cruises, fishing charters

6.2 Miles to St. Armands Circle Boutiques, galleries cafe culture

6.7 Miles to Lido Beach Wide Gulf shoreline with nearby park trails

⏱️ Don t Wait This home books fast. Your reservation includes peace of mind with Vaaraway s enhanced cleaning protocols and elevated guest care.

Need to Know: Free High-Speed WiFi. This pool is heated between November 15 – April 15.

Availability

  • Today
  • Booked
  • Available

Location

Room Details

Room Beds Baths TVs Comments
Bedroom 1
Bedroom 2
Bedroom 3
Bedroom 4
Bathroom 1
Bathroom 2
Bathroom 3
Bathroom 4

Reviews(15)

Don

02/12/2026
Wonderful stay! Great property location in a quiet, residential neighborhood. Beautiful views of the bay and sunsets. Comfortable beds. Fast internet. Plenty of seating inside and out. Plenty of closet storage. Loved having access to kayaks. Loved the pool and hot tub (although, sometimes hard to figure out how the timing of the pool heating worked). Very nice to be able to park in the garage. Unfortunately, the pool and hot tub were not cleaned or heated upon our arrival. It was a couple of days before they were able to be used.

Ann

01/20/2026
The views and amenities were awesome!

Lucienne

01/19/2026
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. 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. 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!

Cindy

12/24/2025
We truly enjoyed our stay at Pearl on the Bay! The house was beautifully decorated and was perfect for our family of four. We enjoyed the pool and the waterfront location. The owners were very responsive to any questions we had.

Brandyn

11/27/2025
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 next door 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

Alex

10/16/2025
We had a wonderful vacation at this beautiful property. The location is perfect…close to great shopping, dining, and the beach. On the days we wanted to simply relax, the home offered plenty to enjoy without leaving. We couldn't have asked for a better place to stay.

Christopher

10/16/2025
Beautiful home with an immaculate view of the water. Amazing upscale, quiet neighborhood situated in the perfect location for going to the beach or downtown. The house has plenty of paddle boards and kayaks, and we saw dolphins swimming every single day. We loved the house and we couldn't have been happier with everything!

Geoanna

10/16/2025
Such a Beautiful Spot. ☝🏾Of my Favorites 🐦☀️☀️☀️☀️🙏🏾💙💗💜🌈

Peter

09/08/2025
Our second stay at this property. Beautiful home and pool. Excellent area, very quiet. The owner was very friendly and attentive to our needs

Chris

08/04/2025
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!

John

07/08/2025
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.

Kathy

06/25/2025
Beautiful, tasteful, home, inside and outside. Everything was superb: furnishings, beds, pool, and the prime location...will definitely return!

Jill

05/23/2025
The house is great, perfect for a family get together. The kitchen is excellent and well equipped (we are a family of cooks) and the overall layout of the house is so comfortable with lots of areas to hang out and enjoy the view. We'll be back for sure.

Jane

04/24/2025
The home was lovely and well managed. The pool was by far my favorite spot!

Tambra

03/11/2025
This home was absolutely beautiful and looked just like the photos. The host was extremely nice and answered any questions we had quickly. Would highly recommend this home and host.
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