$0
for 3 nights

Home in Siesta Key, FL

Ocean Overlook

8 bedrooms

8 beds

9 bathrooms

18 guests

New

4681 sq. ft.

Luxury

Elevated properties with standout design

Operated by a Wander partner

Trusted operators, vetted by Wander

About the property

Ocean Overlook by Siesta Key Luxury Rental Properties

Ocean Overlook by Siesta Key Luxury Rental Properties is an exceptional eight bedroom, eight bathroom coastal retreat with two additional half baths, thoughtfully designed for large families and large group getaways seeking luxury coastal living. Located just a three-minute walk to Siesta Key Beach, this four-story Siesta Key luxury rental offers sweeping Gulf views, large balconies, and a private outdoor oasis. Guests are also a short nine-minute walk to Siesta Key Village, where dining, boutiques, and island nightlife await. With an elevator to all levels, multiple living spaces, and parking for up to five vehicles, Ocean Overlook delivers effortless comfort in one of Sarasota’s most desirable beach locations.

Highlights
• 3-minute walk to Siesta Key Beach
• 8 Bedrooms / 8 Full Bathrooms / 2 Half Bathrooms
• 6 King beds, 1 Queen bed, 1 Full over Full bunk bed
• Private pool with in-ground spa
• Balconies with Gulf views
• Game room with foosball and gaming systems
• Elevator for guest use
• Outdoor dining, BBQ grill, and entertainment space
• Beach chairs, wagon, and cooler provided
• Dog Friendly with host approval and additional fee
• Parking for up to 5 vehicles
• 9-minute walk to Siesta Key Village

This Siesta Key vacation home with pool is centered around an inviting backyard retreat designed for relaxation and entertainment. The private pool features tranquil water elements, lush landscaping, and a connected spa, creating a peaceful setting for afternoons in the sun or evenings under the stars. Nearby, the outdoor kitchen and BBQ area includes a grill, island with built in refrigerator, and multiple dining tables, making it easy to gather for casual meals or celebratory dinners. A shaded outdoor dining bar with seating and a TV adds another layer of comfort, while the outdoor shower and provided beach gear make transitioning from the Gulf to the pool seamless.

The main living level showcases a bright, open concept design with expansive windows framing Gulf views. A spacious living area with comfortable seating and a large TV flows into a fully equipped gourmet kitchen featuring high end appliances, generous counter space, and bar top seating ideal for group cooking and conversation. The formal dining table comfortably accommodates large meals together. Step onto the balcony to enjoy ocean breezes and dine outdoors with stunning views of the Gulf. On the third floor, the game room offers an additional gathering space complete with a wet bar, bar seating, a living area, and a TV. Entertainment continues with a foosball table, PlayStation, and vintage Nintendo console, plus balcony access.

Ocean Overlook offers a collection of thoughtfully designed bedrooms, many functioning as private primary style suites. King bedrooms feature plush bedding, ample closet space, and elegant ensuite bathrooms with walk-in showers, double vanities, and select soaking tubs. Several suites include private balconies, offering quiet spaces to unwind with Gulf views. The Queen bedroom and bunk bedroom each include charming ensuite bathrooms with shower and tub combinations, ideal for families traveling together. Two half baths and conveniently located laundry facilities enhance comfort throughout the home.

Room Details
• Primary Bedroom (3rd Floor): King bed, balcony, ensuite bathroom with double vanity and walk-in shower
• Second Bedroom (3rd Floor): King bed, ensuite bathroom with double vanity, walk-in shower, and soaking tub
• Third Bedroom (3rd Floor): King bed, ensuite bathroom with walk-in shower
• Fourth Bedroom (2nd Floor): King bed, ensuite bathroom with walk-in shower
• Fifth Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with double vanity and walk-in shower
• Sixth Bedroom (2nd Floor): King bed, balcony, ensuite bathroom with walk-in shower
• Seventh Bedroom (2nd Floor): Queen bed, ensuite bathroom with shower and tub combo
• Eighth Bedroom (2nd Floor): Full-over-Full bunk bed, ensuite bathroom with shower and tub combo

Ocean Overlook is ideally positioned along Beach Road, placing guests just minutes from Siesta Key Beach and within a short nine minute walk to Siesta Key Village, home to popular restaurants, beach bars, and boutique shopping. This Siesta Key vacation rental includes an in-home washer and dryer, elevator access to all levels, and parking for up to five vehicles, making extended stays and large group travel effortless.

From sunrise coffee overlooking the Gulf to evenings spent poolside with family and friends, Ocean Overlook by Siesta Key Luxury Rental Properties offers an elevated beach getaway designed for unforgettable moments. With walkable beach access, luxurious indoor and outdoor spaces, and proximity to Siesta Key Village, this home delivers the perfect balance of relaxation and island adventure. Book your stay at Ocean Overlook today and experience the best of Siesta Key luxury living!

-
With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details.

5 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

Please see our Siesta Key Luxury Rental Properties Rental Policies for full details.

This home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Where you’ll sleep

Bedroom 1

1 bed

Bedroom 2

1 bed

Bedroom 3

1 bed

Bedroom 4

1 full bed

Bedroom 5

1 full bed

Bedroom 6

1 full bed

Bedroom 7

1 bed

Bedroom 8

1 full bed

Bedroom 1

1 bed

Bedroom 2

1 bed

Bedroom 3

1 bed

Bedroom 4

1 full bed

Bedroom 5

1 full bed

Bedroom 6

1 full bed

Bedroom 7

1 bed

Bedroom 8

1 full bed

Amenities

Common Amenities

  • Ocean view
  • Game Room
  • Wifi
  • Free parking
  • Beachfront
  • Patio
  • Elevator
  • Ironing board
  • Fire extinguisher
  • Carbon monoxide detector
  • Smoke detector
  • Air conditioning
  • Kitchen
  • Heating
  • Toaster
  • Dedicated workspace
  • Garden
  • Blender
  • Heated pool
  • Hot water
  • Long term stays allowed
  • Baking sheet

Pool

  • Outdoor pool
  • Hot tub
  • Outdoor seating

Rooftop

  • Outdoor seating
  • Ceiling fan

Patio

  • BBQ Area
  • Outdoor seating

Living Room

  • TV

Dining Room

  • Dining table

Kitchen

  • Oven
  • Stove
  • Microwave
  • Fridge
  • Dishwasher
  • Dishes
  • Coffee maker
  • Kettle
  • Wine glasses

Game Room

  • TV
  • Foosball table
  • Fridge
  • Balcony
  • Game console
  • Ceiling fan

Bedroom 1

  • Balcony
  • TV
  • Ceiling fan
  • Bed linens

Ensuite Bathroom 1

  • Bath linens
  • Shampoo
  • Hair dryer

Bedroom 2

  • Bed linens
  • TV
  • Ceiling fan

Ensuite Bathroom 2

  • Bath linens
  • Shampoo

Bedroom 3

  • Bed linens
  • TV
  • Ceiling fan

Ensuite Bathroom 3

  • Bath linens
  • Shampoo

Bedroom 4

  • TV
  • Ceiling fan
  • Bed linens

Ensuite Bathroom 4

  • Bath linens
  • Shampoo

Bedroom 5

  • TV
  • Ceiling fan
  • Bed linens

Ensuite Bathroom 5

  • Bath linens
  • Shampoo

Bedroom 6

  • TV
  • Ceiling fan
  • Bed linens

Ensuite Bathroom 6

  • Bath linens
  • Shampoo

Bedroom 7

  • Bed linens

Ensuite Bathroom 7

  • Bath linens
  • Shampoo

Bedroom 8

  • TV
  • Bed linens

Bathroom 8

  • Bath linens
  • Shampoo

Half Bath 1

  • Bath linens

Half Bath 2

  • Bath linens

Laundry Room

  • Washer
  • Dryer

New · No reviews yet

Be the first to review this place.

Where you’ll be

Siesta Key, FL 34242, US

Siesta Key, FL, US
27.2720095-82.5626261
Timezone: America/New_York

Things to know

Cancellation policy

50% refund up to 30 days before check-in. No refund after that.

Property rules

Pets allowed with fee

No smoking - fees will apply

Events not allowed

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

18 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Oct 17, 2026$1174Not Available
Oct 18, 2026$953Not Available
Oct 19, 2026$953Available
Oct 20, 2026$953Available
Oct 21, 2026$953Available
Oct 22, 2026$953Available
Oct 23, 2026$984Available
Oct 24, 2026$1080Not Available
Oct 25, 2026$953Not Available
Oct 26, 2026$953Not Available
Oct 27, 2026$953Not Available
Oct 28, 2026$953Not Available
Oct 29, 2026$953Not Available
Oct 30, 2026$1278Not Available
Oct 31, 2026$1148Available
Nov 1, 2026$1180Available
Nov 2, 2026$1173Available
Nov 3, 2026$1145Available
Nov 4, 2026$1162Available
Nov 5, 2026$1401Not Available
Nov 6, 2026$1877Not Available
Nov 7, 2026$1809Not Available
Nov 8, 2026$1428Not Available
Nov 9, 2026$1173Not Available
Nov 10, 2026$953Available
Nov 11, 2026$1101Available
Nov 12, 2026$1154Available
Nov 13, 2026$1427Available
Nov 14, 2026$1729Not Available
Nov 15, 2026$1132Not Available
Nov 16, 2026$1071Not Available
Nov 17, 2026$1209Not Available
Nov 18, 2026$1251Not Available
Nov 19, 2026$1376Not Available
Nov 20, 2026$1638Not Available
Nov 21, 2026$2896Not Available
Nov 22, 2026$2896Not Available
Nov 23, 2026$2896Not Available
Nov 24, 2026$2896Not Available
Nov 25, 2026$2896Not Available
Nov 26, 2026$2896Not Available
Nov 27, 2026$2896Not Available
Nov 28, 2026$2896Not Available
Nov 29, 2026$1276Not Available
Nov 30, 2026$1094Not Available
Dec 1, 2026$1001Not Available
Dec 2, 2026$1026Not Available
Dec 3, 2026$1574Not Available
Dec 4, 2026$1807Not Available
Dec 5, 2026$1801Not Available
Dec 6, 2026$1560Not Available
Dec 7, 2026$1545Not Available
Dec 8, 2026$953Available
Dec 9, 2026$953Available
Dec 10, 2026$1165Not Available
Dec 11, 2026$1366Not Available
Dec 12, 2026$1272Not Available
Dec 13, 2026$1102Not Available
Dec 14, 2026$1074Available
Dec 15, 2026$1016Available
Dec 16, 2026$1036Available
Dec 17, 2026$1212Available
Dec 18, 2026$1467Available
Dec 19, 2026$3524Not Available
Dec 20, 2026$3524Not Available
Dec 21, 2026$3524Not Available
Dec 22, 2026$3524Not Available
Dec 23, 2026$3524Not Available
Dec 24, 2026$3524Not Available
Dec 25, 2026$3524Not Available
Dec 26, 2026$4896Not Available
Dec 27, 2026$4875Not Available
Dec 28, 2026$5062Not Available
Dec 29, 2026$4553Not Available
Dec 30, 2026$4553Not Available
Dec 31, 2026$4553Not Available
Jan 1, 2027$4554Not Available
Jan 2, 2027$2041Available
Jan 3, 2027$1580Available
Jan 4, 2027$1504Available
Jan 5, 2027$1398Available
Jan 6, 2027$1398Available
Jan 7, 2027$1677Available
Jan 8, 2027$1779Available
Jan 9, 2027$1779Available
Jan 10, 2027$1499Available
Jan 11, 2027$1447Available
Jan 12, 2027$1367Available
Jan 13, 2027$1383Available
Jan 14, 2027$1785Available
Jan 15, 2027$1951Available