Wander Siesta Key Retreat
Saved to wishlist
24 guests
10 beds
6 bathrooms
Balcony•Outdoor dining area•Beach access
24 guests
8 bedrooms
10 beds
6 bathrooms
1853 sq. ft.
Wander Siesta Key Retreat is a rare dual-home escape just a 2-minute walk from Siesta Key Beach and steps from the vibrant village.
The Wander Guarantee
Book with confidence. Read more.
Check-in & out
Check-in after 4:00pm • Check-out before 10:00am • No pets allowed
Easy cancellation
Cancel within 24 hours for a full refund.
Pristine homes, no to-do lists
Arrive to five star cleaning • No chores at checkout • Just lock up and go
About the property
Hotel-grade amenities
Wander is the best of both worlds. The quality of a luxury hotel with the comfort of a private vacation home just for you and your guests.
Common Amenities
- Wifi
- Free parking
- Hot water
- Fire extinguisher
- Carbon monoxide detector
- Smoke detector
- First aid kit
- Patio
- Balcony
- Air conditioning
- Beach access
Pool
- BBQ Area
- Outdoor dining area
- Outdoor pool
Balcony
- Outdoor seating
Living Room
- TV
- Fire place
Dining Room
- TV
- Dining table
Kitchen 1
- Oven
- Cooking basics
- Stove
- Microwave
- Freezer
- Fridge
- Dishwasher
- Dishes
- Coffee maker
- Coffee
- Kettle
- Tea
- Spices
- Silverware
- Cleaning supplies
- Wine glasses
Bedroom 1
- Ensuite bathroom
- TV
- Bed linens
Ensuite Bathroom 1
- Ensuite bathroom
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Bedroom 2
- TV
- Bed linens
Bedroom 3
- TV
- Bed linens
Ensuite Bathroom 2
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Bedroom 4
- TV
- Bed linens
Bathroom 1
- Ensuite bathroom
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Living Room 2
- TV
- Fire place
Dining Room
- Dining table
Kitchen 2
- Oven
- Cooking basics
- Stove
- Microwave
- Freezer
- Fridge
- Dishwasher
- Dishes
- Coffee maker
- Coffee
- Kettle
- Tea
- Spices
- Silverware
- Cleaning supplies
- Wine glasses
Bedroom 5
- TV
- Bed linens
Bathroom 2
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Bedroom 6
- TV
- Bed linens
Ensuite Bathroom 6
- Shampoo
- Conditioner
- Body soap
Bedroom 7
- Bed linens
- Ensuite bathroom
- TV
Bathroom 3
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Bedroom 8
- TV
- Bed linens
Laundry Room
- Washer
- Dryer
- Cleaning supplies
Where you’ll sleep
Where you’ll be
Nestled on the coveted north end of Siesta Key, this prime location offers easy access to the world-renowned Siesta Key Beach, vibrant St. Armands Circle with over 130 upscale shops and restaurants, and charming nearby attractions.
Restaurants
St. Armands Circle
St. Armands Circle is a vibrant dining hub in Sarasota featuring an eclectic mix of restaurants ranging from upscale French and Spanish cuisine to fresh seafood and casual island-inspired fare, all set within a charming shopping district that blends cultural sophistication with laid-back tropical atmosphere.
Walt's Fish Market Restaurant
Walt's Fish Market is a legendary Sarasota seafood destination where the fish you eat was literally caught in the Gulf the day you buy it, offering fresh catches prepared daily by Chef Rigo in a charming, laid-back tiki bar atmosphere that's been a local favorite for over a century.
Marina Jack
Marina Jack is Sarasota's premier waterfront dining destination, offering three distinct venues from casual beachside patio dining to an upscale second-floor dining room with award-winning wines and fresh seafood, all featuring stunning bay views and live entertainment.
Dry Dock Waterfront Grill
Dry Dock Waterfront Grill offers fresh, expertly prepared seafood and classic American dishes in a relaxed yet polished waterfront setting, featuring panoramic views of Sarasota Bay and a welcoming dockside patio. It's a local favorite for its vibrant flavors and scenic ambiance.
Columbia Restaurant
Columbia Restaurant, Florida’s oldest and the world’s largest Spanish restaurant, offers authentic Spanish-Cuban cuisine in a historic setting with vibrant flamenco shows and an extensive wine collection, creating a lively and elegant dining experience in Tampa’s Ybor City.
Owen's Fish Camp -Downtown SRQ
Owen's Fish Camp is a beloved Sarasota seafood destination nestled under a historic banyan tree, serving fresh Gulf catches and Southern classics in a casual, laid-back atmosphere that captures the essence of old Florida living. With its lively bar scene, live music, and warm hospitality, it's the perfect spot for an unforgettable meal among family and friends.
Siesta Key Oyster Bar
Siesta Key Oyster Bar (SKOB) is a laid-back beachfront hotspot in Siesta Key Village serving fresh oysters, award-winning wings, and creative seafood with a fun, tropical atmosphere complete with dollar bills adorning the ceiling and live music nightly.
Connors Steak & Seafood
Connors Steak & Seafood serves premium aged steaks and fresh seafood grilled over wood fires for a unique flavor. Enjoy upscale dining with excellent service, a lively bar, and a menu that satisfies every craving.
Captain Curt's Crab & Oyster Bar
Captain Curt's Crab & Oyster Bar is a beloved Old Florida seafood restaurant on Siesta Key famous for its award-winning clam chowder and fresh catch, offering a relaxed island atmosphere with indoor and outdoor dining, live music, and a welcoming family-friendly vibe that keeps locals and visitors coming back.
Detwiler's Farm Market
Detwiler's Farm Market offers a vibrant farm-to-table experience with fresh produce, an old-fashioned butcher shop, Amish-style deli meats, a bakery, and an ice cream shop, all wrapped in a warm, hometown atmosphere. It’s a one-stop destination for quality, fresh food at great prices.
Marina Jack
Marina Jack is Sarasota's premier waterfront dining destination offering three distinct venues—from the casual, breezy Blue Sunshine Patio to the sophisticated Dining Room—all serving exceptional seafood, steaks, and pasta with stunning bay views and live entertainment.
St. Armands Circle
St. Armands Circle offers a vibrant dining scene with a variety of options, from fresh Gulf seafood and bold, creative dishes to Mediterranean and island-inspired flavors, all set in inviting atmospheres ranging from casual tropical vibes to elegant, panoramic beach views. Whether you crave Spanish tapas, Italian classics, or innovative coastal fare, this cultural hub delivers memorable meals with friendly service.
Walt's Fish Market Restaurant
Walt's Fish Market Restaurant in Sarasota offers the freshest seafood caught daily, served in a relaxed, tropical setting featuring a lively tiki bar and live music, blending a century-old family tradition with modern, flavorful dishes.
Dry Dock Waterfront Grill
Dry Dock Waterfront Grill is a polished-casual waterfront dining destination on Longboat Key renowned for its award-winning fresh grouper sandwich and Gulf seafood specialties, offering panoramic views of Sarasota Bay from both its upstairs dining room and dockside patio.
Columbia Restaurant
Columbia Restaurant is Florida's oldest and the world's largest Spanish restaurant, serving authentic Cuban and Spanish cuisine since 1905 in historic Ybor City with nightly Flamenco performances, elegant dining rooms, and an internationally acclaimed wine collection.
Owen's Fish Camp -Downtown SRQ
Owen's Fish Camp in downtown Sarasota serves fresh, Southern-style seafood in a relaxed, historic setting with a lively bar scene and scenic outdoor seating.
Siesta Key Oyster Bar
Siesta Key Oyster Bar offers a lively, beachy vibe with fresh seafood, award-winning wings, and cold drinks, all served in a fun, tropical setting with live music and friendly service. It’s the perfect spot to enjoy island spirit and great food in Siesta Key Village.
Connors Steak & Seafood
Connors Steak & Seafood is an upscale steakhouse specializing in premium aged steaks and fresh seafood, expertly prepared over wood-fired grills to deliver exceptional flavor in a refined dining atmosphere. With multiple locations across the Southeast and consistent recognition as a top-rated restaurant, it offers an impressive wine selection and memorable service for both casual lunch and special occasions.
Captain Curt's Crab & Oyster Bar
Captain Curt's Crab & Oyster Bar serves up fresh seafood and award-winning clam chowder in a relaxed, nautical setting with both indoor and outdoor dining. Enjoy live music, a lively bar, and a true taste of Old Florida on Siesta Key.
Attractions
St. Armands Circle
St. Armands Circle offers a unique blend of upscale shopping, diverse dining, and charming outdoor spaces on a scenic island, perfect for visitors who enjoy a lively yet relaxed coastal atmosphere with a touch of history and culture. It’s ideal for shoppers, food lovers, and those seeking a picturesque day out.
Marie Selby Botanical Gardens Downtown Sarasota
Marie Selby Botanical Gardens Downtown Sarasota offers a unique bayfront oasis featuring the world’s only botanical garden dedicated to epiphytic orchids, bromeliads, and tropical plants, perfect for nature lovers, families, and anyone seeking a vibrant, educational outdoor experience.
Lido beach
Lido Beach is a sunny paradise perfect for families, where you can build sandcastles, paddle through mangrove tunnels, and spot playful dolphins. With calm waters, fun activities, and plenty of space to relax, it’s a favorite spot for kids and adults alike.
Bayfront Park
Bayfront Park in Miami offers a vibrant waterfront escape with scenic bay views, live music venues, unique monuments, and fun activities like flying trapeze and free yoga, making it perfect for families, fitness lovers, and culture seekers.
Sarasota Opera House
Experience world-class opera performances in an elegantly restored 1,100-seat historic theater in downtown Sarasota, where you can enjoy timeless classics like La bohème and The Merry Widow alongside fine dining and shopping. Perfect for culture enthusiasts seeking an unforgettable evening of music, drama, and theatrical splendor.
Siesta Key Watersports
Soar 1,000 feet above crystal-clear Gulf waters while spotting dolphins and manatees, or throttle across the Intracoastal Waterway on a jet ski—Siesta Key Watersports delivers thrilling aerial views and high-speed adventures perfect for thrill-seekers and families alike.
Sarasota Art Museum
Experience world-class contemporary art, lively music, and creative workshops in a vibrant campus that blends history and innovation. Perfect for art lovers, families, and anyone seeking inspiration and connection in a welcoming, dynamic setting.
Pinecraft Amish Community
Step into the heart of Pinecraft, where Amish and Mennonite traditions blend with Florida sunshine for a truly unique cultural experience. Visitors love the friendly vibe, handmade crafts, and delicious Amish food in this charming, bike-friendly neighborhood.
Unconditional Surrender - Sarasota, FL
Stand before a towering 26-foot bronze sculpture immortalizing one of history's most iconic moments—a sailor and nurse embracing at the end of World War II. Perfect for history enthusiasts, photographers, and anyone seeking a meaningful waterfront experience that captures the joy and relief of peace.
St. Armands Circle
St. Armands Circle is a charming, walkable island district with upscale shops, lively restaurants, and a scenic park, perfect for those who love shopping, dining, and soaking up Sarasota’s vibrant coastal atmosphere.
Lido beach
Lido Beach is a pristine Gulf Coast destination perfect for families and nature lovers seeking a blend of relaxation and adventure, offering everything from building sandcastles and paddling through enchanting mangrove tunnels to spotting dolphins and enjoying fresh seafood at beachside cafes.
Pinecraft Amish Community
Pinecraft is a unique Amish and Mennonite snowbird community in Sarasota where visitors can experience a simpler way of life through shuffleboard games, handcrafted goods, and authentic home-cooked meals, making it perfect for anyone curious about traditional culture or seeking a relaxed, distinctive Florida getaway.
Marie Selby Botanical Gardens Downtown Sarasota
Marie Selby Botanical Gardens is a world-renowned bayfront oasis featuring over 20,000 exotic plants, including the world's largest collection of orchids and air plants, making it perfect for nature lovers, families, and photographers seeking a tropical escape in the heart of Sarasota.
Payne Park
Payne Park is a lively, family-friendly destination featuring a unique circus-themed playground, a popular skate park, disc golf, tennis courts, and scenic trails, perfect for outdoor enthusiasts and kids of all ages looking for fun and adventure in Sarasota.
Bayfront Park
Bayfront Park is a vibrant waterfront oasis in downtown Miami, perfect for families, fitness enthusiasts, and culture lovers with its scenic baywalk, playgrounds, live performances, flying trapeze classes, and dazzling musical fountain shows. It offers something special for everyone seeking outdoor fun and city views.
Sarasota Opera House
Experience the magic of world-class opera in the historic Sarasota Opera House, where timeless stories and stunning performances captivate both seasoned opera lovers and newcomers alike. Perfect for anyone who enjoys powerful music, dramatic tales, and elegant ambiance.
Siesta Key Watersports
Siesta Key Watersports offers thrilling parasailing, jet ski rentals, and scenic dolphin tours perfect for adventure seekers and nature lovers looking to explore crystal-clear waters and stunning coastal views. It’s ideal for families, beginners, and experienced water sports enthusiasts alike.
Unconditional Surrender - Sarasota, FL
Stand before a towering 26-foot bronze sculpture recreating the iconic V-J Day kiss that symbolized the end of World War II—a powerful monument to history and a must-see photo opportunity for anyone visiting Sarasota's picturesque bayfront.
Sarasota Art Museum
Experience art, music, and dance under the stars at Sarasota Art Museum’s After Hours, a monthly celebration perfect for adults and art lovers looking for a vibrant night out with live performances and creative energy.
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Things to know
Here are some things which you should know before booking Wander Siesta Key Retreat
Check-in: after 4:00 pm
Check-out: before 10:00 am
24 guests maximum
No pets allowed
No smoking - fees will apply
Events require approval
Cancel within 24 hours for a full refund.
Check-in: after 4:00 pm
Check-out: before 10:00 am
24 guests maximum
No pets allowed
No smoking - fees will apply
Events require approval
Before you book
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Feb 23, 2026 | $5254 | Not Available |
| Feb 24, 2026 | $5254 | Not Available |
| Feb 25, 2026 | $5254 | Not Available |
| Feb 26, 2026 | $5254 | Not Available |
| Feb 27, 2026 | $6695 | Not Available |
| Feb 28, 2026 | $8208 | Not Available |
| Mar 1, 2026 | N/A | Not Available |
| Mar 2, 2026 | N/A | Not Available |
| Mar 3, 2026 | N/A | Not Available |
| Mar 4, 2026 | N/A | Not Available |
| Mar 5, 2026 | N/A | Not Available |
| Mar 6, 2026 | N/A | Not Available |
| Mar 7, 2026 | $8352 | Not Available |
| Mar 8, 2026 | $8425 | Not Available |
| Mar 9, 2026 | $8425 | Not Available |
| Mar 10, 2026 | $7373 | Not Available |
| Mar 11, 2026 | $6265 | Not Available |
| Mar 12, 2026 | $6210 | Not Available |
| Mar 13, 2026 | $7162 | Not Available |
| Mar 14, 2026 | $8114 | Not Available |
| Mar 15, 2026 | $8114 | Not Available |
| Mar 16, 2026 | $8114 | Not Available |
| Mar 17, 2026 | $8114 | Not Available |
| Mar 18, 2026 | $8114 | Not Available |
| Mar 19, 2026 | $8114 | Not Available |
| Mar 20, 2026 | $10819 | Not Available |
| Mar 21, 2026 | $13524 | Not Available |
| Mar 22, 2026 | N/A | Not Available |
| Mar 23, 2026 | N/A | Not Available |
| Mar 24, 2026 | N/A | Not Available |
| Mar 25, 2026 | N/A | Not Available |
| Mar 26, 2026 | N/A | Not Available |
| Mar 27, 2026 | N/A | Not Available |
| Mar 28, 2026 | $14490 | Not Available |
| Mar 29, 2026 | $14490 | Not Available |
| Mar 30, 2026 | $14490 | Not Available |
| Mar 31, 2026 | $14490 | Not Available |
| Apr 1, 2026 | $14490 | Not Available |
| Apr 2, 2026 | $14490 | Not Available |
| Apr 3, 2026 | $14490 | Not Available |
| Apr 4, 2026 | $14490 | Not Available |
| Apr 5, 2026 | $14490 | Not Available |
| Apr 6, 2026 | $14490 | Not Available |
| Apr 7, 2026 | $14490 | Not Available |
| Apr 8, 2026 | $14490 | Not Available |
| Apr 9, 2026 | $14490 | Not Available |
| Apr 10, 2026 | $11620 | Not Available |
| Apr 11, 2026 | $8846 | Not Available |
| Apr 12, 2026 | $8942 | Not Available |
| Apr 13, 2026 | $8942 | Not Available |
| Apr 14, 2026 | $8942 | Not Available |
| Apr 15, 2026 | $8942 | Not Available |
| Apr 16, 2026 | $8942 | Not Available |
| Apr 17, 2026 | $9425 | Not Available |
| Apr 18, 2026 | $10005 | Not Available |
| Apr 19, 2026 | N/A | Not Available |
| Apr 20, 2026 | N/A | Not Available |
| Apr 21, 2026 | N/A | Not Available |
| Apr 22, 2026 | N/A | Not Available |
| Apr 23, 2026 | N/A | Not Available |
| Apr 24, 2026 | N/A | Not Available |
| Apr 25, 2026 | $6615 | Not Available |
| Apr 26, 2026 | $6675 | Not Available |
| Apr 27, 2026 | $6675 | Not Available |
| Apr 28, 2026 | $6675 | Not Available |
| Apr 29, 2026 | $6555 | Not Available |
| Apr 30, 2026 | $6677 | Not Available |
| May 1, 2026 | $4067 | Not Available |
| May 2, 2026 | $2836 | Not Available |
| May 3, 2026 | N/A | Not Available |
| May 4, 2026 | N/A | Not Available |
| May 5, 2026 | N/A | Not Available |
| May 6, 2026 | N/A | Not Available |
| May 7, 2026 | N/A | Not Available |
| May 8, 2026 | N/A | Not Available |
| May 9, 2026 | $2781 | Not Available |
| May 10, 2026 | N/A | Not Available |
| May 11, 2026 | N/A | Not Available |
| May 12, 2026 | N/A | Not Available |
| May 13, 2026 | N/A | Not Available |
| May 14, 2026 | N/A | Not Available |
| May 15, 2026 | N/A | Not Available |
| May 16, 2026 | $3143 | Not Available |
| May 17, 2026 | N/A | Not Available |
| May 18, 2026 | N/A | Not Available |
| May 19, 2026 | N/A | Not Available |
| May 20, 2026 | N/A | Not Available |
| May 21, 2026 | N/A | Not Available |
| May 22, 2026 | N/A | Not Available |
| May 23, 2026 | $3851 | Not Available |
| May 24, 2026 | N/A | Not Available |