My Happy Place Home Sarasota My Happy Place Back to Search Results My Happy Place Plenty of seating in the living room with large Smart TV and perfect for family gatherings. Spacious and open dining area with kitchen breakfast bar with additional seating, and an open living room with access to private screened in balcony. Dining room with plenty and additional seating at beautiful breakfast bar. Primary bedroom with King size bed, fresh quality linens, ceiling fan, and large window . Kitchen fully equipped with coffee maker, appliances, cookware, utensils, and glassware. Open Gallery Plenty of seating in the living room with large Smart TV and perfect for family gatherings. Spacious and open dining area with kitchen breakfast bar with additional seating, and an open living room with access to private screened in balcony. Dining room with plenty and additional seating at beautiful breakfast bar. Primary bedroom with King size bed, fresh quality linens, ceiling fan, and large window . Kitchen fully equipped with coffee maker, appliances, cookware, utensils, and glassware. Screened in private balcony with seating and sunset views, opens up to main living room. Just a 2-minute drive to top rated Siesta Key Beach. Heated pool just steps away from the condo. Tennis courts available for outdoor family fun activities. Private dock perfect for fishing or manatee viewing! Spacious primary bedroom with King sized bed, large window with view, opens up to bathroom and large vanity space. Spacious primary bedroom with King sized bed, high quality comfortable bedding, with attached bathroom. Spacious primary bedroom with King sized bed, high quality comfortable bedding, with dresser and closet for storage, and large attached bathroom. Primary bedroom with French doors that open up to spacious bathroom with large vanity. French doors open up to well-lit vanity with bathroom and closet access. Well-lit vanity with bathroom, plush towels, shower, and closet access. Walk in shower off primary bedroom with plush bath towels available and bath essentials. Second bedroom with two full-sized beds and spacious closet. Includes a Smart TV for streaming. Second bedroom with two full-sized beds and spacious closet. Second bedroom with two full-sized beds, Smart TV, large window with views, and spacious closet. Main bathroom with shower tub combo and bathroom essentials. Plush clean bath towels provided. Entryway table with fobs for pool and tennis areas, and parking pass. Entryway leads to Primary and Secondary bedrooms. Open concept space perfect for family gatherings. Includes private walk out balcony with seating and peaceful views. Perfect for enjoying a morning coffee before a day at Siesta Key Beach! Open concept space perfect for family gatherings. Large dining area with seating for six. Two bar stools for seating at breakfast bar overlooking the kitchen area. Open concept space perfect for family gatherings. Smart TV for streaming or movie night with friends and family. Open concept space with plenty of seating, perfect for family gatherings or movie night. Plenty of seating in the living space with patio access, perfect for family gatherings or movie night. Open concept space perfect for relaxing or family dinners. Cozy living area opens up to dining room and private balcony. Relaxing balcony with seating for two and perfect for sunset views or a morning coffee. Relaxing balcony with seating. Perfect for peaceful relaxation after a day at Siesta Key Beach. Relaxing private screened-in balcony with seating. Opens up to main living room area. Private screened-in balcony opens up to main living room area. Private screened-in balcony with outdoor seating opens up to cozy living room area. Spacious breakfast bar with seating and plenty of glassware for a perfect bottle of wine or a quick breakfast meal. Kitchen overlooks dining room and main living space. Kitchen overlooks breakfast bar, dining room, and main living space. Dishwasher and laundry room right off the kitchen area for convenience. Fully stocked kitchen with plenty of cooking essentials, cutlery, glassware and everything you need for a perfect meal at home. Fully stocked kitchen with plenty of cooking essentials and counter space for meal preparation. Full-size in-unit washer and dryer unit just off the kitchen area. Main entryway. Unit is on 4th floor. Elevator and stairs near the unit for easy access. Outdoor seating and tables, pool loungers and heated pool. Large oak trees surround the property and gorgeous walkway with bench seating. Picnic tables available just outside the unit. Private dock with seating perfect for a quite morning or evening sunset and manatee viewing. Quite waterway with dock seating for relaxing and sunset views. Private dock with seating perfect for manatee viewing. Private dock with seating. Siesta Key Public Beach Access, Pavilion, and Free Public Parking Exterior view of the building 1 Exterior view of the building 2 Aerial view of Siesta Key Beach condo with access to quiet canal. Aerial view of Siesta Key Beach condo. Just a 2-minute drive to top rated Siesta Key Beach. Aerial view of Siesta Key Beach condo with heated pool. Large pool and just a 2-minute drive to top rated Siesta Key Beach. Aerial view of Siesta Key Beach. Aerial view of tennis court and Siesta Key Beach. Aerial view of the canal near the condo with private dock seating. Parking space - parking pass provided in the condo. Gallery View Siesta Key, Florida 2 Bedrooms 2 full Baths 4 Guests 1101 sq. ft. (5.0) Description Rooms Amenities Reviews Calendar Location Escape to the tranquil beauty of Siesta Key in this inviting 2-bedroom, 2-bath condo located in the picturesque Bay Oaks community. Surrounded by mature live oak trees, lush landscaping, and access to peaceful bayfront views, this charming 4th-floor retreat offers comfort, convenience, and the perfect beach getaway. Property Highlights: • Located in the scenic Bay Oaks complex on Siesta Key's bayside • Lined with beautiful live oak trees and manicured tropical landscaping • Short 3 min drive to world-famous Siesta Key Beach for sun, sand, and sunsets • Access to heated swimming pool, tennis court, and private bayside dock—great for fishing or watching boats glide by • Includes beach essentials: chairs, umbrella • Free Trolley access with a trolley stop across the street. Condo Features: • Situated on the 4th floor with elevator access • Cozy, open living space with coastal-inspired decor and plenty of natural light • Closed-in porch with large sliders—open for fresh Gulf breezes or enjoy views of the garden and a peek of the Gulf in the distance Bedrooms and Bathrooms: • Primary bedroom includes a king-size bed, plush linens, a SMART TV, walk-in closet, and ensuite bathroom. Ensuite features a separate vanity area and a pocket door leading to a walk-in shower • Guest bedroom has two twin beds, a SMART TV, walk-in closet, and ensuite access to a full bathroom. Guest bathroom offers dual entry from the hallway and guest room, with a shower/tub combo, plush towels, and a vanity Kitchen and Amenities: • Fully equipped kitchen with all white appliances and everything needed for cooking and dining in • Private in-unit washer and dryer for added convenience • Dining table and comfortable seating for relaxing evenings at home Whether you're lounging by the pool, taking a stroll to the beach, or relaxing in the comfort of your breezy porch, this Bay Oaks condo offers the perfect blend of coastal charm, privacy, and resort-style amenities. Ideal for couples, families, or snowbirds looking to enjoy the Siesta Key lifestyle in a serene, well-kept community. Please Note: Guests will need to use a Public Beach Access point. Siesta Key Beach Public Access & Pavilion is a 3-minute drive north of the condo (or a 15-20 minute walk). This public access has free parking and a ton of great amenities and rental options. There is a free Trolley stop just across the street for easy transportation around the island. There is another Public Beach Access for Crescent Beach south of the condo which is about a 5-minute drive or 20-25 minute walk. There is limited parking so arriving early is best. The Beauty of Siesta Key Siesta Key is a barrier island positioned between the Gulf and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids. The Siesta Key Village offers a wide selection of shops, cafes, top restaurants, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate. Trolley transportation is available around the island and throughout Sarasota. Rooms Primary Bedroom 1 King Guest Bedroom 2 Twin Amenities Location & Attractions Car - Not Necessary Family Themed Marina Museums Ocean Nearby Zoo Bay Beach Access Car - Recommended View - Garden Village Bedroom & Laundry Wardrobe or Closet Bed Linens Essentials Extra Pillows & Blankets Hangers Iron & Ironing Board Dryer - Private Washer - Private Cleanliness & Safety Common Surfaces Disinfected Deadbolt Lock Disinfectant Used While Cleaning Fire Extinguisher Outdoor Lighting Linens High Temp Wash (140 degrees) Self Check-In & Check-Out Smoke Detector Sports, Leisure & Adventure Eco Tourism Antiquing Bird Watching Boating Cycling Diving Fishing Fishing - Bay Fishing - Deep Sea Fishing - Fly Fishing - Freshwater Fishing - Pier Fishing - Surf Golf Horseback Riding Jet Skiing Outlet Shopping Parasailing Sailing Shopping Snorkeling Swimming Wildlife Viewing Paddle Boating Wind Surfing Bathroom Body Soap Conditioner Hair Dryer Hot Water Shampoo Shower Gel Towels Bathtub Entertainment TV Smart TV Internet & Office Laptop Friendly Workspace Wifi Wifi - Free Ethernet Connection Wifi - Speed 500mbps Kitchen & Dining Coffee Coffee Maker Cooking Basics Dishes & Silverware Freezer Kitchen Microwave Oven Refrigerator Stove Toaster Baking Sheet Blender Dining Area or Room Dining table Dishwasher Kitchen Island Wine Glasses Other Building, Complex Or Neighborhood Amenities Hospital Courtyard - Community Tennis Court - Community Other Property Amenities Air Conditioning Ceiling Fan Heating Private Entrance Living Room Pets - Not Allowed Parking & Facilities Parking - Free Elevator Parking - On Site Free Services Concierge - Available Outdoor BBQ Grill Area BBQ Grill - Community BBQ Grill - Gas Beach Essentials Outdoor Seating & Furniture Patio or Balcony Sun Loungers Pool & Spa Pool Pool - Community Pool - Heated See All Amenities + Reviews 5.0 (4 Reviews) Write A Review Thank you for submitting your review. It will be processed shortly! We value your privacy. Your email address will not be shared publicly. SUBMIT AnneMarie Habetler Stayed Jun, 2026 Beautiful Condo in Siesta Key! We had the pleasure of staying at “My Happy Place”. This place is so perfect for a relaxing vacation! Great location! This 2 bed, 2 bath condo is updated, clean, and has all the amenities you ask for in a perfect location! We will definitely return! The owner and SkyRun Rentals keep this unit on top top shape! I highly recommend renting this beautiful unit! You are walking distance to Captain Curt’s, the Daiquiri Deck, and shopping. LOVE THIS PLACE! ? Joyce Gorsky Stayed Jan, 2026 It\'s called MY HAPPY PLACE for a good reason! We were fortunate to secure part of our winter in FL in this condo on Siesta Key this past January. (through half of February). The condo is very well appointed, it\'s clean and in a perfect location on Siesta Key. Sky Run management is also wonderful, and if you have any questions, they are happy to answer any and all. I would highly recommend you consider staying in this condo while vacationing in Siesta Key. We were so happy with our stay that we booked next year as soon as we left to go home. Cannot wait for our next visit! Angela Ferrazza Stayed Sep, 2025 Perfect Siesta Key Stay! This 4th-floor end unit was absolutely wonderful. The location is ideal—situated on the intercoastal waterway with a lovely peek-a-boo view of the Gulf, and easy access by either elevator or stairs. One of my favorite parts of the stay was sitting out on the pier, watching boats drift by and spotting dolphins. The condo itself is beautifully furnished, with comfortable beds and brand-new furniture throughout. The kitchen was very well equipped for cooking, and there were plenty of towels, beach chairs, and an umbrella provided, which made beach days effortless. The surrounding area was just as fantastic. We loved the great restaurants nearby, and the trolley made it so easy to get to Siesta Village and the public beach without needing to drive. Overall, a perfect place to relax and enjoy everything Siesta Key has to offer. Highly recommend - excited to return to this condo. Jaime Ferry Stayed Nov, 2025 Will Definitely Return! After staying 4 amazing days in this condo, we’ll definitely be coming back every time we visit Sarasota. The location was perfect, close to everything, and the pool, tennis courts, and the bay were the perfect combination for a fun and relaxing short vacation. We felt like we were home away from home and wished we didn’t have to leave. Thank you for an incredible stay, we’ll definitely be returning, hopefully soon! Availability Select your travel dates to view a detailed quote. 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