$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
Sep 20, 2026$979Not Available
Sep 21, 2026$979Not Available
Sep 22, 2026$979Not Available
Sep 23, 2026$979Not Available
Sep 24, 2026$979Not Available
Sep 25, 2026$987Not Available
Sep 26, 2026$979Not Available
Sep 27, 2026$979Available
Sep 28, 2026$979Available
Sep 29, 2026$979Available
Sep 30, 2026$979Available
Oct 1, 2026$979Available
Oct 2, 2026$1205Available
Oct 3, 2026$1298Not Available
Oct 4, 2026$979Not Available
Oct 5, 2026$1331Not Available
Oct 6, 2026$1012Not Available
Oct 7, 2026$1044Not Available
Oct 8, 2026$1385Not Available
Oct 9, 2026$1726Not Available
Oct 10, 2026$1838Not Available
Oct 11, 2026$1560Not Available
Oct 12, 2026$1353Not Available
Oct 13, 2026$1285Not Available
Oct 14, 2026$1025Available
Oct 15, 2026$1398Not Available
Oct 16, 2026$1797Not Available
Oct 17, 2026$1919Not Available
Oct 18, 2026$1424Not Available
Oct 19, 2026$1182Available
Oct 20, 2026$1110Available
Oct 21, 2026$1323Available
Oct 22, 2026$1473Available
Oct 23, 2026$1679Available
Oct 24, 2026$1834Not Available
Oct 25, 2026$1563Not Available
Oct 26, 2026$1494Not Available
Oct 27, 2026$1400Not Available
Oct 28, 2026$1403Not Available
Oct 29, 2026$1551Not Available
Oct 30, 2026$1790Not Available
Oct 31, 2026$1614Available
Nov 1, 2026$1422Available
Nov 2, 2026$1416Available
Nov 3, 2026$1397Available
Nov 4, 2026$1412Available
Nov 5, 2026$1695Not Available
Nov 6, 2026$2005Not Available
Nov 7, 2026$1950Not Available
Nov 8, 2026$1612Not Available
Nov 9, 2026$1509Not Available
Nov 10, 2026$1354Available
Nov 11, 2026$1481Available
Nov 12, 2026$1523Available
Nov 13, 2026$1809Available
Nov 14, 2026$1887Not Available
Nov 15, 2026$1463Not Available
Nov 16, 2026$1389Not Available
Nov 17, 2026$1303Not Available
Nov 18, 2026$1331Not Available
Nov 19, 2026$1511Not Available
Nov 20, 2026$1811Not Available
Nov 21, 2026$2896Available
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$1437Not Available
Nov 30, 2026$1265Not Available
Dec 1, 2026$1121Not Available
Dec 2, 2026$1155Not Available
Dec 3, 2026$1695Not Available
Dec 4, 2026$1945Not Available
Dec 5, 2026$1945Not Available
Dec 6, 2026$1695Not Available
Dec 7, 2026$1696Not Available
Dec 8, 2026$979Available
Dec 9, 2026$979Available
Dec 10, 2026$1272Not Available
Dec 11, 2026$1497Not Available
Dec 12, 2026$1406Not Available
Dec 13, 2026$1205Not Available
Dec 14, 2026$1142Available
Dec 15, 2026$1080Available
Dec 16, 2026$1120Available
Dec 17, 2026$1293Available
Dec 18, 2026$1556Available
Dec 19, 2026$3524Not Available