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Siesta Key Retreat
Siesta Key, Florida

Wander Siesta Key Retreat

Wander Siesta Key Retreat

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24 guests
10 beds
6 bathrooms
1/62
BalconyOutdoor dining areaBeach 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.
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Flexible check-in & out
Check-in after 4:00pm • Check-out before 10:00amNo 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

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. Designed for large groups and multi-family stays, this 8-bedroom retreat features two private heated pools, spacious balconies, outdoor dining lounges, and two full kitchens, offering the perfect balance of togetherness and privacy. Enjoy cabana rooms, beach gear, two garages, smart TVs, fast WiFi, and hotel-style starter amenities, plus dog-friendly options and island shuttle access. Sleeping up to 24 guests, this bright coastal getaway delivers the ultimate Siesta Key experience with beach days, village nights, and endless poolside relaxation.
Property License: N/A

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

Living Room
1 queen sofa
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 queen bed
Living Room 2
1 queen sofa
Bedroom 5
1 king bed
Bedroom 6
1 king bed
Bedroom 7
1 king bed
Bedroom 8
1 queen bed
Living Room
1 queen sofa
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 queen bed
Living Room 2
1 queen sofa
Bedroom 5
1 king bed
Bedroom 6
1 king bed
Bedroom 7
1 king bed
Bedroom 8
1 queen bed

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.
Siesta Key, Florida, United States
27.2745484-82.56310189999999
Timezone: America/New_York

Getting there

S Tamiami Trl @ Kestral Park Way

S Tamiami Trl @ Kestral Park Way offers convenient bus connections, including line 17, linking South Sarasota to key destinations like the University of South Florida Sarasota-Manatee, making it a vital transit hub for local and regional travel.

Swift Rd @ Hope St

I don't have information available about a specific transportation hub located at Swift Rd @ Hope St. The search results provided don't contain details about this particular location or its transit services. To provide an accurate description, I would need information about which city this location is in and what transportation services operate there.

Sarasota Bradenton Intl. Airport

Sarasota Bradenton International Airport offers a modern, spacious terminal with two concourses, convenient services like free Wi-Fi, pet relief areas, and easy accessibility, making travel smooth and comfortable for all passengers. Its new observation deck and apron-level views add a unique experience.

Sarasota Bradenton International Airport

Sarasota Bradenton International Airport offers a modern, easy-to-navigate terminal with direct flights from major U.S. carriers, accessible services, and convenient ground transportation options, making it a stress-free gateway to Florida’s Gulf Coast. Its recent expansion includes new gates, dining, and an observation deck.

Swift Rd @ Hope St

Swift Rd @ Hope St is a convenient bus stop in Sarasota, providing easy access to local shops, residences, and key city routes for commuters and visitors alike. Its sheltered waiting area makes it a practical transit point for navigating the area.

S Tamiami Trl @ Kestral Park Way

S Tamiami Trl @ Kestral Park Way is a convenient transit stop in South Sarasota offering easy connections via bus routes to key destinations like the University of South Florida Sarasota-Manatee and nearby neighborhoods. It serves as a local hub for efficient travel across the area.

Sarasota Bradenton International Airport

Sarasota Bradenton International Airport offers convenient access to Florida’s Gulf Coast with modern terminals, free Wi-Fi, accessible services, and a variety of ground transportation options including taxis, shuttles, and rental cars. Its new concourse features spacious gates, dining, and panoramic airfield views.

Sarasota Bradenton Intl. Airport

Sarasota Bradenton International Airport offers stress-free travel with 65+ nonstop flights, easy access for all passengers, and modern amenities like free Wi-Fi, pet relief areas, and convenient ground transportation.

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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Wander Guarantee Badge
Guests love Wander
Wander's average ratings
Cleanliness
4.8
Location
4.8
Check-in
4.8
Value
4.8
Concierge Quality
4.8
Wow Factor
4.9

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Things to know

Here are some things which you should know before booking Wander Siesta Key Retreat
HOUSE RULES
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
CANCELLATION POLICY
Cancel within 24 hours for a full refund.

Before you book

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Nov 25, 2025$4680Not Available
Nov 26, 2025$6553Not Available
Nov 27, 2025N/ANot Available
Nov 28, 2025$4536Not Available
Nov 29, 2025$2520Not Available
Nov 30, 2025$2328Not Available
Dec 1, 2025$2075Not Available
Dec 2, 2025$2043Not Available
Dec 3, 2025$2326Not Available
Dec 4, 2025$2644Not Available
Dec 5, 2025$2898Not Available
Dec 6, 2025$3025Not Available
Dec 7, 2025$2709Available
Dec 8, 2025$2614Available
Dec 9, 2025$2773Available
Dec 10, 2025$2773Available
Dec 11, 2025$2773Available
Dec 12, 2025$2773Available
Dec 13, 2025$2773Available
Dec 14, 2025$2646Available
Dec 15, 2025$2487Available
Dec 16, 2025$2455Available
Dec 17, 2025$2455Available
Dec 18, 2025$2328Available
Dec 19, 2025$4712Available
Dec 20, 2025$7222Available
Dec 21, 2025$7222Available
Dec 22, 2025$7307Available
Dec 23, 2025$8305Available
Dec 24, 2025$9218Not Available
Dec 25, 2025N/ANot Available
Dec 26, 2025N/ANot Available
Dec 27, 2025$11334Not Available
Dec 28, 2025$11334Not Available
Dec 29, 2025$11677Not Available
Dec 30, 2025$12020Not Available
Dec 31, 2025N/ANot Available
Jan 1, 2026N/ANot Available
Jan 2, 2026N/ANot Available
Jan 3, 2026$3731Not Available
Jan 4, 2026$3678Not Available
Jan 5, 2026$3636Not Available
Jan 6, 2026$3756Not Available
Jan 7, 2026$3756Not Available
Jan 8, 2026$3675Not Available
Jan 9, 2026$3595Not Available
Jan 10, 2026$3434Not Available
Jan 11, 2026$3353Available
Jan 12, 2026$3314Available
Jan 13, 2026$3356Available
Jan 14, 2026$3517Available
Jan 15, 2026$3597Available
Jan 16, 2026$4147Available
Jan 17, 2026$4600Available
Jan 18, 2026$4407Available
Jan 19, 2026$4359Available
Jan 20, 2026$4407Available
Jan 21, 2026$4503Available
Jan 22, 2026$4600Not Available
Jan 23, 2026$4600Not Available
Jan 24, 2026$4600Not Available
Jan 25, 2026$4600Not Available
Jan 26, 2026$4648Not Available
Jan 27, 2026$4697Not Available
Jan 28, 2026$4697Not Available
Jan 29, 2026$4793Available
Jan 30, 2026$6406Available
Jan 31, 2026$7933Available
Feb 1, 2026$7944Available
Feb 2, 2026N/ANot Available
Feb 3, 2026N/ANot Available
Feb 4, 2026N/ANot Available
Feb 5, 2026N/ANot Available
Feb 6, 2026N/ANot Available
Feb 7, 2026$8430Available
Feb 8, 2026$8430Available
Feb 9, 2026$8513Available
Feb 10, 2026$8596Available
Feb 11, 2026$8596Available
Feb 12, 2026$8596Available
Feb 13, 2026$10034Available
Feb 14, 2026$11473Not Available
Feb 15, 2026$11473Not Available
Feb 16, 2026N/ANot Available
Feb 17, 2026N/ANot Available
Feb 18, 2026N/ANot Available
Feb 19, 2026N/ANot Available
Feb 20, 2026N/ANot Available
Feb 21, 2026$5377Not Available
Feb 22, 2026$5522Not Available
Feb 23, 2026N/ANot Available
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