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2783::The Pearl on the Bay - 1370

Bedrooms: 4

Bathrooms: 4

Sleeps: 10

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Exclusive Amenities Include: ↑↓

Welcome to The Compass Collection, where luxury meets tranquility on the waterfront. Immerse yourself in a haven of opulence with our exclusive amenities designed for the perfect retreat.
Indulge in the serenity of your own private heated pool and spa while soaking in breathtaking Intracoastal views. Our carefully curated collection of accommodations boasts 4 master bedrooms, each with its own full bath, featuring a total of 3 king beds and 2 queen beds—perfect for accommodating up to 10 guests with linens provided.
Savor outdoor dining in a blissful atmosphere, or cast a line from our fishing dock equipped with underwater lights for an enchanting evening. Unwind by the outdoor fire table or on the spacious balcony deck overlooking the bay, complete with lounging and exterior dining areas.
Convenience meets luxury with a private 2-car garage, free WiFi, and 5 HD Smart TVs for your entertainment. Our state-of-the-art Wolf / Subzero kitchen appliances, regular and Keurig coffee maker, washer and dryer set, and essential kitchen supplies ensure a seamless stay.
We've thought of every detail to enhance your experience, providing starter packs of toiletry essentials and home essentials, including shampoo, conditioner, soap, body lotion, dish soap, dishwasher tablets, laundry tablets, and more.
Beach enthusiasts will appreciate our complimentary beach towels, chairs, cooler, and caddy, while the outdoor lounge area beckons with a private heated pool, spa, fire table, hammocks, crows nest, gas grill, and more. Dive into adventure with 1 kayak and 2 paddle boards at your disposal.
Rest easy knowing our enhanced cleaning protocols, administered by our meticulous CottageClean Team, prioritize your well-being. Plus, take advantage of island shuttle transportation for added convenience.
Experience a seamless blend of luxury and leisure at The Compass Collection—your exclusive retreat by the bay. Book your stay today and discover a world of unparalleled comfort and sophistication.

Overview ↑↓

Discover The Pearl on the Bay, an idyllic waterfront haven for your perfect vacation retreat. Located just off Siesta Key in the prestigious San Remo neighborhood, this exquisite home offers unparalleled water views and an unforgettable escape.
Inside, experience thoughtful design and full amenities. Stay connected with free WiFi and indulge in entertainment with five HD smart TVs. The chef's dream kitchen boasts top-of-the-line Wolf and Subzero appliances, along with a regular and Keurig coffee maker, dishwasher, and essential kitchen supplies.
With four master bedrooms, each designed for ultimate comfort and privacy, and a total of three king beds and two queen beds accommodating up to 10 guests, find luxury and space effortlessly. Linens are provided for your convenience, ensuring a seamless and relaxing stay.
Upon arrival, a starter pack of toiletry essentials and home essentials awaits you, making settling in a breeze. Step into the backyard to discover your private tropical oasis, complete with an expansive heated pool and spa overlooking the intracoastal. Lounge on plush poolside furniture, take a refreshing dip, or soak in the spa, surrounded by lush landscaping.
For adventure seekers, the fishing dock with underwater lights and provided kayak and paddle boards offer exciting opportunities to explore the Gulf Coast waters. Enjoy a home-cooked meal at the outdoor dining space, relax on the hammock, or ascend the spiral staircase to the crow's nest for panoramic views.
As the sun sets, gather around the outdoor fire table for cozy evenings under the stars. The Pearl on the Bay seamlessly blends luxury, comfort, and natural beauty, providing an unmatched vacation experience. Create lasting memories in this stunning waterfront retreat.
Accommodation details:
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 (2) - sleeps: 4
Please note: The pool is heated from November 15th to April 15th.
Rest assured with our meticulous multi-tiered cleaning protocol within our program, ensuring your safety and satisfaction. Experience worry-free vacationing with The Pearl on the Bay—a sanctuary of beauty and tranquility.

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Stunning setting and location.

Review Date: May 13, 2024

"Stunning setting and location. Can't be beat!! Cool just needed a little cleaning and upkeep nothing too major. They responded to my request to clean it directly and we're on top of customer service.

Reviewed By: Rodney

Place, views, pool were awesome!

Review Date: April 24, 2024

"Place, views, pool were awesome! No need to go anywhere else. Just stay and enjoy the home, pool and gourmet kitchen!

Reviewed By: Greg

The sunsets on the balcony are just stunning and I can't wait to go back!!

Review Date: April 16, 2024

"A stunning property that's in a stunning location. Watch the boats pass by all day. Dolphin, stingray and many other forms of wildlife make regular visits to the dock. The sunsets on the balcony are just stunning and I can't wait to go back!!

Reviewed By: Neil

Wonderful property right on Sarasota Bay. This is the second stay for us.

Review Date: April 16, 2024

"Wonderful property right on Sarasota Bay. This is the second stay for us. It had everything we needed as a family. Plenty of space. Fully stocked kitchen. Very clean. Quick drive to all islands and attractions or full of fun things to do if we decided to just stay in all day and play in the pool. Thanks for letting us use this beautiful property!

Reviewed By: Kimberly

A fabulous home in a stunning location!

Review Date: April 9, 2024

"A fabulous home in a stunning location!

Reviewed By: Neil

Beautiful property. As advertised and better.

Review Date: March 21, 2024

"Beautiful property. As advertised and better. It was so relaxing. Felt like home. Tastefully decorated and well appointed. The property managers were professional and prompt in dealing with any issue. Would stay again in a heartbeat.

Reviewed By: Peter

Review for The Pearl on the Bay - 1370

Review Date: June 28, 2023

"The house was the perfect place for our family! We will be back!

Reviewed By: Anne

Review for The Pearl on the Bay - 1370

Review Date: May 15, 2023

"We stayed at Pearl on the Bay and had a wonderful time. The highlight is the location, right on the intracoastal waterway with lots going on. The kids loved the dolphins and manatees going by. The house is spacious with everything you might need. Support from Cottages on the Key is exceptional. Good time was had by all.

Reviewed By: David

Paradise on the Bay

Review Date: April 13, 2023

"We were very pleased with our experience. The house was large enough for all families to have their own space and great common areas for eating, playing games, napping, and enjoying the back patio. The property management company was extremely attentive and helped us think thru options of having food delivered to the house so it was ready after a long travel day. Dolphins swam by the house multiple times a day and boat watching was plentiful. We will definitely return!

Reviewed By: Kimberly

Beautiful

Review Date: November 14, 2022

"Beautiful property enjoyed dolphin watching and sunsets. The house is well appointed

Reviewed By: Tammy

Best vacation experience ever!

Review Date: August 2, 2022

"Our family has been coming to Florida renting different properties for the last 15 years. Working with Cottages on the Key and staying at the Pearl on the Bay was by far our best vacation experience ever. The team at the Cottages on the Key was extremely pleasant and professional to work with. When we checked in on Saturday, we had freshly made cupcakes waiting for us. The house was very clean and spacious. Everything was easy to find. This is a beautiful location both secluded and quiet. Short drive to Siesta Key beach and plenty of options for entertainment, places to eat etc. The Pearl on the Bay was even better than the pictures online show. We loved the views from the backyard of the intracoastal, pool and beautiful sunsets. We didn't want to leave the property that often because it was so relaxing just hanging out in the back area. We went kayaking and used the paddle boards several times. The fishing off the dock was great. I caught several speckled trout, redfish, and sheepshead. You can easily fish at night with the dock lighting and underwater lights. We had a truly amazing stay. Thank you, Cottages on the Key!! We would love to come back again.

Reviewed By: Jeff

Our New Favorite Getaway!

Review Date: July 22, 2022

"What an outstanding experience and vacation at the Pearl on the Bay. To begin, the home is beautiful with gorgeous views. We sat out watching dolphins from the patio and enjoyed endless hours in the pool. It's the little things they think of like the hammocks and pool basketball net that put it over the top for us. The floor plan is accommodating for large families that love to be together but enjoy a little space to themselves as well. The staff was great and communicative whenever we needed anything and they left us delicious cupcakes for our arrival. Thank you for providing us with the perfect setting for our annual trip. We will be back next year and are already looking forward to it!

Reviewed By: Jennifer

Perfect Paradise

Review Date: June 27, 2022

"I can't rave enough about our experience here. The house is fully renovated and just excellent for family groups to dine, socialize, and play. The location is superb - access to grocery store is a mere couple blocks away to minutes from the restaurants and shops. The amenities are perfect - the kitchen and that pool are just great. And that view… right on the intercostal bay and a pool side to boot. We loved every moment.

Reviewed By: Joseph

Airbnb review

Review Date: February 28, 2022

"The place was as advertised. Clean, well-equipped with plenty of beach towels, linens etc. Management was responsive to any questions we had on timely basis. Working the heater for pool is through iPad which had to be rebooted a couple of times but otherwise no problem. We had a group of nine (4 couples plus one) for a C long weekend and while the place does sleep ten (more if you count sofas and hammocks

Reviewed By: Anonymous