$0
for 3 nights

Home in Sarasota, Florida

Ocean Overlook

8 bedrooms

8 beds

9 bathrooms

18 guests

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!

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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

4.8 · 27 reviews

G

Gretchen B.

August 2026

This home was located in a prime location. It was within walking distance to several beach accesses, restaurants, shopping and a grocery store. The sunsets from the balcony were amazing! The layout was perfect for our group.
J

Jayan N.

October 2025

The rental was absolutely perfect—clean, comfortable, and with stunning views overlooking Siesta Key Beach. Just a two-minute walk to the village and all the great eateries, it couldn’t be more convenient. The owners were incredibly responsive and kind, making the entire stay seamless. Highly recommended for a relaxing beach getaway
K

Karli G.

January 2024

WoW! Amazing beach view from the 3rd and 4th floors. Very comfortable beds, nice linens, extra pillows, easy to do laundry! The walk to the beach was so close and the walk to town also so close. It is truly the PERFECT location! We enjoyed the two living and hang out areas! It would have been good to have more games and a few throw blankets. The kitchen had all we needed. We made a big family dinner and had breakfasts there too. Never needed a single thing that was not there. We did have to got the store for dish soap, shampoo, conditioner, laundry detergent and paper towels. They supply small ones but they did not last more then two days. But you can WALK to the grocery! The pool and hot tub were great for the adults + kids and covered for when it rained (once!). We loved it and would stay again!

Where you’ll be

Sarasota, Florida 34242, United States

Sarasota, Florida, United States
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
Nov 11, 2026$953Available
Nov 12, 2026$953Available
Nov 13, 2026$953Available
Nov 14, 2026$1044Not Available
Nov 15, 2026$953Not Available
Nov 16, 2026$953Not Available
Nov 17, 2026$953Not Available
Nov 18, 2026$953Not Available
Nov 19, 2026$953Not Available
Nov 20, 2026$1268Not 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$1010Not Available
Nov 30, 2026$953Not Available
Dec 1, 2026$953Not Available
Dec 2, 2026$953Not Available
Dec 3, 2026$1382Not Available
Dec 4, 2026$1662Not Available
Dec 5, 2026$1685Not Available
Dec 6, 2026$1372Not Available
Dec 7, 2026$1341Not Available
Dec 8, 2026$953Available
Dec 9, 2026$953Available
Dec 10, 2026$968Not Available
Dec 11, 2026$1264Not Available
Dec 12, 2026$1203Not Available
Dec 13, 2026$1016Not Available
Dec 14, 2026$962Available
Dec 15, 2026$953Available
Dec 16, 2026$953Available
Dec 17, 2026$1100Available
Dec 18, 2026$1349Available
Dec 19, 2026$2535Available
Dec 20, 2026$2497Available
Dec 21, 2026$2519Available
Dec 22, 2026$2515Available
Dec 23, 2026$2539Available
Dec 24, 2026$2612Available
Dec 25, 2026$2711Available
Dec 26, 2026$4589Not Available
Dec 27, 2026$4503Not Available
Dec 28, 2026$4660Not Available
Dec 29, 2026$4219Not Available
Dec 30, 2026$4223Not Available
Dec 31, 2026$4208Not Available
Jan 1, 2027$4263Not Available
Jan 2, 2027$1860Available
Jan 3, 2027$1452Available
Jan 4, 2027$1377Available
Jan 5, 2027$1266Available
Jan 6, 2027$1266Available
Jan 7, 2027$1599Available
Jan 8, 2027$1732Available
Jan 9, 2027$1732Available
Jan 10, 2027$1350Available
Jan 11, 2027$1300Available
Jan 12, 2027$1230Available
Jan 13, 2027$1263Available
Jan 14, 2027$1785Available
Jan 15, 2027$1951Available
Jan 16, 2027$1951Available
Jan 17, 2027$1748Available
Jan 18, 2027$1414Available
Jan 19, 2027$1348Available
Jan 20, 2027$1309Available
Jan 21, 2027$1478Available
Jan 22, 2027$1709Available
Jan 23, 2027$1727Available
Jan 24, 2027$1494Available
Jan 25, 2027$1697Available
Jan 26, 2027$1393Available
Jan 27, 2027$1431Available
Jan 28, 2027$1604Available
Jan 29, 2027$1890Available
Jan 30, 2027$1943Available
Jan 31, 2027$1668Available
Feb 1, 2027$1649Available
Feb 2, 2027$1595Available
Feb 3, 2027$1661Available
Feb 4, 2027$1915Available
Feb 5, 2027$2284Available
Feb 6, 2027$2310Available
Feb 7, 2027$1994Available
Feb 8, 2027$1949Available
Feb 9, 2027$1852Available