The Pearl by the Sea – 5258

The Pearl by the Sea - 5258
4 Bedrooms 3 Bathrooms House in Siesta Key
from $4043 per /wk

Property Details

Property Description

Welcome to The Pearl by the Sea, one of Siesta Key’s most luxurious canal homes with private heated pool and spa! This home is perfect for large families and groups.

Property Details

This home qualifies for our Book Care Free option for 2020 arrivals which includes:
• Only $99 down
• 24 hour cancellation policy
• Deferred deposit payments until 14 days prior to your arrival
Ask us about how you can qualify for this special offer!

We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have improved and strengthened our cleaning crews by mandating the highest quality products that are EPA approved to use against COVID-19. Our cleaners also have a longer period of time to complete this thorough process to ensure a full cleaning of all items. After this initial cleaning, we require the cleaning company manager to assess the job completed and assign any additional areas to be cleaned. Furthermore, right before your arrival, we have a quality control team that conducts a 50-point pre arrival inspection on this home and reapplies the approved products once again right before your walk into your beautiful home. We extensively re-clean every light switch, lamp, door knob, surface, remote, hard back chair, and any area that is considered a high volume touch surface with approved disinfectant cleaning material. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our cleaning services have enhanced protocols in place to ensure that you feel tremendously safe and happy with this amazing home. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!

This one-of-a-kind, limited edition canal home offers all of the amenities for your Siesta Key getaway at an unbeatable location near world famous Siesta Key Beach, voted the # 1 beach in the USA! Welcome to paradise!

The Pearl by the Sea can accommodate up to 10 guest 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: Sleeper Sofa (1) - Sleeps: 2
• Extra: Rollaway Bed (2) - Sleeps: 2

Exclusive Amenities Include:

• Private Heated Pool
• Spa
• Boat Dock
• Located on Canal
• Kitchen Essentials Provided
• Coffee Maker (Regular + Built-In)
• Linens Provided
• Dog-Friendly (up to 20 lbs.)
• Bicycles (4)
• Kayaks (2)
• Outdoor Grill
• Beach Towels
• Cooler
• Beach Caddy
• Outdoor Lounge Area
• Beach Chairs
• Access to The Black Pearl (exclusive to The Cottages guests’ only!)
• Free WiFi

Your reservation must follow under the accordance of the Sarasota County code regulations.

This property has 3 King(s), 1 Pull Out Sofa(s), 2 Rollaway(s).
Booking Calendar

Availability & Booking Calendar


Property Location



  • Concierge - Other Services
  • Bay
  • Coin Laundry
  • Health Beauty Spa
  • Marina
  • Museums
  • Parks
  • Water Parks
  • Winery Tours
  • Zoo
  • Satellite / Cable
  • Television
  • Air Conditioning
  • Central Heat
  • Clothes Dryer
  • Garage
  • Hair Dryer
  • Heating
  • Internet - Hi Speed
  • Internet - Wireless
  • Iron and Board
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Cookware
  • Dining Area
  • Dining Spices
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Antiquing
  • Bird Watching
  • Boating
  • Eco Tourism
  • Gambling
  • Outlet Shopping
  • Paddle Boat
  • Shopping
  • Water Sports
  • Wildlife Viewing
  • Hospital
  • Laundromat
  • Beach
  • Near Ocean
  • Village
  • Water View
  • Waterfront
  • Balcony
  • Bicycle
  • Deck/Patio
  • Gas Grill
  • Kayak
  • Lanai / Gazebo
  • Heated Pool
  • Hot Tub
  • Private Pool
  • Basketball Court
  • Biking
  • Deep Sea Fishing
  • Fishing
  • Fishing Bay
  • Fishing Fly
  • Fishing Surf
  • Golf Optional
  • Golfing
  • Hiking
  • Jet Skiing
  • Kayaking
  • Paragliding
  • Parasailing
  • Pier Fishing
  • Roller Blading
  • Sailing
  • Scuba or Snorkeling
  • Snorkeling
  • Surfing
  • Swimming
  • Water Skiing
  • Water Tubing
  • Wind Surfing
  • Family
  • Luxury
  • Romantic
Rates & Policies


Weekly Rate: $4043 - $5775 per week
- Rate varies due to seasonality and holidays.
- Please select your dates on our online booking calendar for an exact quote.


Accomodations Tax - 12.00%
Accidental Damage Protection $3000 Coverage - $75.00
Lost and Found Fees - $0.00 - Tax Exempt
Exit Cleaning Fee - $365.00
Pet Fee - $250.00
Administrative fee - 9.00%
Cancellation Policy
CANCELLATION POLICY / TRIP INSURANCE NOTICE: Regarding this reservation process, The Cottages on the Key Company is creating a legal, binding contract between the property owner and the guests to insure the desired benefits to each of the parties. The Cancellation Policy for prime season rentals [December – April, June-August] stipulates that any rental deposit amount and any additional payments made are refundable less any administrative fees up to ninety [90] days prior to the beginning of the rental period. After 90 days prior to the rental period, the Licensor shall have the uncontested right to retain the initial Deposit and any other payments received. If you cancel and your check-in date is more than ninety [90] days away, you will receive a refund of your deposit less the administrative fee by credit card refund within 15 days of your written cancellation notice. The Cancellation Policy for all other reservations in the periods of September – November, and May stipulates that any rental deposit amount and any payments are refundable less any administrative fees up to seven [7] days prior to the beginning of the rental period. After 7 days prior to the rental period, the Licensor shall have the uncontested right to retain the initial Deposit and any other payments received. The Cottages on the Key company strongly recommends purchasing a TRIP INSURANCE POLICY to insure recovery of your deposit/payments made and potentially retained by this Cancellation Policy to avoid loss during unforeseen circumstances. We recommend researching trip insurance companies online. We also offer an option of purchasing trip insurance at the time of your booking with The Cottages on the Key upon request. Guests may also purchase the trip insurance up to 24 hours prior to their arrival. Please note: there is an option for cancelling for any reason (CFAR) up to 20 days within the initial deposit date. We would recommend you research this type of policy from various providers to include iTravelInsured:

Please note: if you booked using a 3rd party affiliate (i.e. HomeAway or VRBO), please refer to their cancellation policy for your records.
Last updated 08/04/2020
Deposit Policy
Please sign online with digital signature. This agreement must be returned to us within 48 hours, as we cannot guarantee your requested dates without receipt of a signed rental agreement. In order to finalize your reservation, we require the initial deposit plus a credit card on file to cover any incidentals and negligent damages.
Last updated 08/04/2020

Guest Reviews

The Pearl by the Sea by Doug & Heidi N. 07/05/2019
We had a wonderful time during our stay at Pearl by the Sea. We have booked three times now with The Cottages on the Key. We would highly recommend your company to anyone looking for a luxurious and relaxing stay in Siesta Key and the surrounding area. We look forward to our next stay with you.
Pearl by the Sea by Sheri P. 04/09/2019
We stayed at Pearl By The Sea and it was a wonderful home! Fun and modern, pool was perfect, location was excellent, close to beach and village! The Cottages staff went above and beyond to make sure our stay was perfect. One person spent a few hours with us working thru a cable issue to be sure we could utilize the TV's. Highly recommend renting with the Cottages, they make sure your time in Siesta is stress free!!
House is absolutely fantastic! by Sally R. 01/04/2019
This house is fantastic and we would certainly stay again. The standard and quality of the furnishings etc. are superb. It is located on the canal with great views from the outside area and pool. The house is only a short distance from the village and beach and we made good use of the bikes to get around. I would certainly recommend this rental and hope to stay there again one day!