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Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience

Waterfront holiday home with private pool and kitchen

Photo gallery for Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience

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.
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.

Reviews

9.6 out of 10
Exceptional
4 bedrooms4 bathroomsSleeps 83506 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Explore the area

View in a map
Sarasota, FL
  • Place, Coconuts Family Entertainment Center
    ‪3 min drive‬
  • Place, St. Armands Circle
    ‪12 min drive‬
  • Place, Lido Beach
    ‪13 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪16 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

4 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Outdoor play area
Dining area

About this property

Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience

🌊 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.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly

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House Rules

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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Sarasota

Located on the waterfront, this holiday home is in San Remo, a neighbourhood in Sarasota. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Looking to enjoy an event or a game while in town? See what's happening at Ed Smith Stadium or Sarasota Kennel Club. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Sarasota, FL

What's nearby

  • Coconuts Family Entertainment Center - 3 min drive - 2.7 km
  • Sarasota Memorial Hospital - 3 min drive - 3.1 km
  • St. Armands Circle - 12 min drive - 10.5 km
  • Lido Beach - 13 min drive - 10.9 km
  • Mall at University Town Center - 20 min drive - 17.2 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 25 min drive

Restaurants

  • ‪McDonald's - ‬17 min walk
  • ‪Red Barn Bar - ‬19 min walk
  • ‪CinéBistro - ‬19 min walk
  • ‪Connors - ‬2 min drive
  • ‪Walt's Fish Market - ‬3 min drive

Frequently asked questions

Does Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience?

On-site parking is available at the property.

Where is Pearl on the Bay - A breathtaking Pool & Bayfront property - an unparalleled vacation experience located?

Located in San Remo, this holiday home is 1.2 mi (1.9 km) from Coconuts Family Entertainment Center and within 3 miles (5 km) of Shell Beach and The Landings. Sarasota Memorial Hospital and Irma Beach are also within 3 miles (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 8 out of 9 reviews
Rating 8 - Good. 0 out of 9 reviews
Rating 6 - Okay. 1 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.4/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

Reviews

10/10 Excellent

Ann M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The views and amenities were awesome!
Stayed 7 nights in Jan 2026

10/10 Excellent

Cindy J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Dec 2025

10/10 Excellent

Guido A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House is in a great location with a great layout. Very well equiped kitchen, good beds and linens. Nice kayaks, with dock lift. Very nice and responsive owners to any questions and issues.
Stayed 14 nights in Nov 2025

10/10 Excellent

Alex W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Sep 2025

10/10 Excellent

Peter A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our second stay at this property. Beautiful home and pool. Excellent area, very quiet. The owner was very friendly and attentive to our needs
Stayed 14 nights in Aug 2025

10/10 Excellent

Chris S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Oct 2025

10/10 Excellent

Jane B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect week

The home was lovely and well managed. The pool was by far my favorite spot!
Stayed 7 nights in Mar 2025

10/10 Excellent

Jill C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible Property

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.
Stayed 6 nights in May 2025

6/10 Okay

Stephanie H.

Liked: Cleanliness, check-in, location
Disliked: Listing accuracy
The house is in a great location and the bay scenery is beautiful, however there were a few things that for the price point should not have happened. For example, we had a toddler with us and in the room gallery of photos for the listing there was a misleading image of a bathtub in the home. There are no bathtubs, only showers. The microwave did not work and there seems to have been a circuit issue that my handy husband ended up fixing while we were there. These may seem like small things but when you are traveling with small kids these are game changers. For adults the home has everything.
Stayed 5 nights in Aug 2025

About the host

Hosted by Vaaraway

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Premier Host

They consistently provide great experiences for their guests
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