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
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.
Bedroom 4
1 full bed
Ensuite Bathroom 4
1 full bed
Bedroom 5
1 full bed
Bedroom 6
1 full bed
Bedroom 8
1 full bed
Laundry Room
1 full bed
Entry
1 full bed
Bedroom 4
1 full bed
Ensuite Bathroom 4
1 full bed
Bedroom 5
1 full bed
Bedroom 6
1 full bed
Bedroom 8
1 full bed
Laundry Room
1 full bed
Entry
1 full bed
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Siesta Key, FL 34242, US
Siesta Key, FL, USDiscover Florida's oldest restaurant, the Columbia in historic Ybor City, where five generations serve authentic Spanish-Cuban cuisine amid 15 vibrant dining rooms spanning an entire block. Savor iconic 1905 Salad and flamenco dinner shows in this lively landmark.
I'd be happy to help, but I need clarification: which restaurant at St. Armands Circle would you like me to describe? The search results cover multiple dining options including Columbia Restaurant (Spanish/Cuban cuisine), Café L'Europe (French), Crab & Fin (seafood), and others. Please specify which restaurant you'd like featured.
Savor world-famous clam chowder and fresh oysters at Captain Curt's Crab & Oyster Bar, a family-friendly Siesta Key gem blending casual Old Florida vibes, live music, and indoor-outdoor seating near the beach.[1][2][3][4]
Savor premium aged steaks and fresh seafood grilled over mesquite wood for an unforgettable smoky flavor at Connors Steak & Seafood. This upscale American steakhouse delivers exceptional service and quality in a welcoming ambiance perfect for any occasion.
Detwiler's Farm Market is a hometown grocery destination offering fresh, locally-sourced produce, quality meats, seafood, and an Amish-style deli alongside a bakery and sub shop, creating a bustling market atmosphere where customers discover unique, hard-to-find items unavailable at mainstream stores.
Marina Jack is Sarasota's premier waterfront dining destination featuring award-winning seafood, steaks, and pasta with stunning bay views across three distinct venues—from the casual, live-music-filled Blue Sunshine Patio to the sophisticated second-floor Dining Room.
Savor fresh Gulf seafood like grouper sandwiches and lobster rolls at Dry Dock Waterfront Grill, a casual Longboat Key gem with panoramic Sarasota Bay views from its dockside patio. Hearty portions and award-winning al fresco vibes make it a local favorite since 1989.
Walt's Fish Market is a beloved Sarasota seafood destination serving the freshest local catch since 1918, with fish literally caught the day you buy it. The laid-back tiki bar atmosphere, complete with live music and handcrafted cocktails, makes it an authentic Florida dining experience for locals and visitors alike.
Nestled under a historic banyan tree in downtown Sarasota, Owen's Fish Camp delivers fresh Gulf seafood and Southern classics like shrimp and grits in a lively, casual atmosphere with live music and tire swings. Dive into old Florida charm with creative cocktails and exceptional hospitality.
Siesta Key Oyster Bar is a laid-back beachside hotspot in Siesta Key Village serving fresh seafood, award-winning wings, and craft cocktails in a fun, eccentric atmosphere complete with dollar bills covering the walls and live music nightly.
Visit this iconic 26-foot statue inspired by the famous V-J Day Times Square kiss photograph—a must-see landmark that sparks conversation about history and art. Perfect for history buffs, photographers, and anyone seeking a unique photo opportunity at this beloved Sarasota bayfront attraction.
Experience world-class opera performances in a beautifully renovated historic theater in downtown Sarasota, where you can enjoy classic works like La bohème, The Merry Widow, and Il trovatore through March. Perfect for both seasoned opera enthusiasts and newcomers seeking an elegant evening of unforgettable entertainment.
Siesta Key Watersports offers thrilling parasailing, jet ski rentals, and dolphin-watching tours with USCG-certified captains and a perfect safety record spanning over 28 years, making it ideal for adventure seekers and families wanting to experience Siesta Key from the water.
Discover the enchanting St. Armands Circle, a circus-inspired island gem in Sarasota Bay boasting over 130 upscale shops, galleries, and eateries around a lush central park with coastal vibes. Shopaholics, foodies, and history buffs will love its lively European charm and beach proximity.[1][2][4]
Lido Beach offers pristine white sand and calm, crystal-clear waters perfect for families and beach lovers of all ages, with nearby amenities, stunning sunsets, and easy access to water activities like paddleboarding and kayaking through scenic mangrove tunnels.
Marie Selby Botanical Gardens is a stunning 15-acre bayfront oasis featuring over 6,000 orchids, lush tropical conservatories, and scenic mangrove walkways along Sarasota Bay—perfect for nature lovers, families, and anyone seeking a peaceful escape into world-class botanical beauty.
Sway to live music and themed dance lessons under the stars at Sarasota Art Museum's After Hours, blending world-class art, cocktails, and moves from country to salsa. Perfect for music lovers, dancers, and anyone craving a vibrant night out with friends.[1][4]
Discover Payne Park's circus-inspired playground with splash pads, rock climbing, and swings for kids, plus a skate park, disc golf, and trails for all ages. Families, thrill-seekers, and pet owners love this vibrant downtown Sarasota gem perfect for picnics and play.
Bayfront Park is a stunning 32-acre waterfront escape in downtown Miami where you can enjoy tree-lined paths, bay views, and public art installations, perfect for families, fitness enthusiasts, and anyone seeking relaxation by the water with easy access to shopping and dining at nearby Bayside Marketplace.
Discover a unique slice of Amish culture in sunny Florida at Pinecraft, where thousands of Amish snowbirds vacation during winter months to enjoy recreational sports, authentic handcrafted goods, and legendary homemade pies at famous establishments like Yoder's. Perfect for curious travelers seeking an authentic cultural experience and those who appreciate traditional craftsmanship and comfort food.
Free cancellation up to 14 days before check-in. No refund after that.
Pets allowed with fee
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
18 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 15, 2026 | $979 | Not Available |
| Jul 16, 2026 | $1057 | Not Available |
| Jul 17, 2026 | $1710 | Not Available |
| Jul 18, 2026 | $1519 | Not Available |
| Jul 19, 2026 | $979 | Not Available |
| Jul 20, 2026 | $979 | Not Available |
| Jul 21, 2026 | $979 | Not Available |
| Jul 22, 2026 | $979 | Not Available |
| Jul 23, 2026 | $1368 | Not Available |
| Jul 24, 2026 | $1901 | Not Available |
| Jul 25, 2026 | $1737 | Not Available |
| Jul 26, 2026 | $1198 | Not Available |
| Jul 27, 2026 | $1145 | Not Available |
| Jul 28, 2026 | $1074 | Not Available |
| Jul 29, 2026 | $1090 | Not Available |
| Jul 30, 2026 | $1470 | Not Available |
| Jul 31, 2026 | $1855 | Not Available |
| Aug 1, 2026 | $1868 | Not Available |
| Aug 2, 2026 | $1657 | Not Available |
| Aug 3, 2026 | $1630 | Not Available |
| Aug 4, 2026 | $1584 | Not Available |
| Aug 5, 2026 | $1587 | Not Available |
| Aug 6, 2026 | $1639 | Not Available |
| Aug 7, 2026 | $1815 | Not Available |
| Aug 8, 2026 | $1726 | Not Available |
| Aug 9, 2026 | $1416 | Not Available |
| Aug 10, 2026 | $1193 | Available |
| Aug 11, 2026 | $1194 | Not Available |
| Aug 12, 2026 | $1240 | Not Available |
| Aug 13, 2026 | $1293 | Not Available |
| Aug 14, 2026 | $1538 | Not Available |
| Aug 15, 2026 | $1488 | Not Available |
| Aug 16, 2026 | $1398 | Not Available |
| Aug 17, 2026 | $1119 | Available |
| Aug 18, 2026 | $1044 | Available |
| Aug 19, 2026 | $1291 | Available |
| Aug 20, 2026 | $1343 | Not Available |
| Aug 21, 2026 | $1453 | Not Available |
| Aug 22, 2026 | $1481 | Not Available |
| Aug 23, 2026 | $1380 | Not Available |
| Aug 24, 2026 | $1500 | Available |
| Aug 25, 2026 | $1301 | Available |
| Aug 26, 2026 | $1316 | Available |
| Aug 27, 2026 | $1457 | Available |
| Aug 28, 2026 | $2084 | Available |
| Aug 29, 2026 | $2073 | Available |
| Aug 30, 2026 | $2002 | Available |
| Aug 31, 2026 | $1085 | Available |
| Sep 1, 2026 | $1325 | Available |
| Sep 2, 2026 | $1327 | Available |
| Sep 3, 2026 | $1204 | Available |
| Sep 4, 2026 | $1502 | Not Available |
| Sep 5, 2026 | $1560 | Not Available |
| Sep 6, 2026 | $1339 | Not Available |
| Sep 7, 2026 | $1228 | Not Available |
| Sep 8, 2026 | $979 | Available |
| Sep 9, 2026 | $979 | Available |
| Sep 10, 2026 | $1188 | Not Available |
| Sep 11, 2026 | $1382 | Not Available |
| Sep 12, 2026 | $1233 | Not Available |
| Sep 13, 2026 | $1025 | Not Available |
| Sep 14, 2026 | $979 | Not Available |
| Sep 15, 2026 | $979 | Available |
| Sep 16, 2026 | $979 | Available |
| Sep 17, 2026 | $1126 | Not Available |
| Sep 18, 2026 | $1275 | Not Available |
| Sep 19, 2026 | $1416 | Not Available |
| Sep 20, 2026 | $1155 | Not Available |
| Sep 21, 2026 | $1071 | Not Available |
| Sep 22, 2026 | $1000 | Not Available |
| Sep 23, 2026 | $1031 | Not Available |
| Sep 24, 2026 | $1212 | Not Available |
| Sep 25, 2026 | $1391 | Not Available |
| Sep 26, 2026 | $1392 | Not Available |
| Sep 27, 2026 | $1212 | Available |
| Sep 28, 2026 | $1036 | Available |
| Sep 29, 2026 | $979 | Available |
| Sep 30, 2026 | $990 | Available |
| Oct 1, 2026 | $1617 | Available |
| Oct 2, 2026 | $1704 | Available |
| Oct 3, 2026 | $1601 | Not Available |
| Oct 4, 2026 | $1601 | Not Available |
| Oct 5, 2026 | $1601 | Not Available |
| Oct 6, 2026 | $1129 | Not Available |
| Oct 7, 2026 | $1188 | Not Available |
| Oct 8, 2026 | $1524 | Not Available |
| Oct 9, 2026 | $1828 | Not Available |
| Oct 10, 2026 | $1828 | Not Available |
| Oct 11, 2026 | $1679 | Not Available |
| Oct 12, 2026 | $1469 | Not Available |
| Oct 13, 2026 | $1393 | Not Available |