Remarks: This property is on the market and as of now will not be renting in 2027. Booked June 6th-13th, June 20th-July 26th, Nov 21st-28th, Dec 21st to 31st 2026. Lovely remodeled and refurbished 5 bedroom 5.5 bath pool home on desirable St. Armand's Circle! This 3,000 s.f. home comfortably sleeps 8, and has T.V.'s in the family room and living room for when the family is not enjoying the caged pool and spa, or investigating St. Armand's Circle or Lido Beach. Professionally decorated, quality surrounds you whether it be the wonderful appliances, the new furniture or the luxurious bedding. There is seating at the dining table for 8 and room for more at the breakfast bar. There is also a bedroom and bathroom located over the garage. Walk 150 yards to St. Armand's for dinner or night out, before returning to a lighted heated pool and spa to end the evening. The pool deck is complete with recliners, chairs and a dining table for real outdoor living. Retire to comfy new beds which will ensure a blissful sleep to start the new day. Visit this home once and you will return! There is a gate to the driveway but it is not operational at this time. There are many places to visit around the area some of those include, Mote Marine, Selby Gardens, Marina Jacks, Island Park, and many theatre options as well. You can also find that adventurous side and go water skiing, boating, golfing, or just relax on one of our luxurious beaches. This property is leased on a first come, first serve basis. If we reply the property is available, it is at that moment, but may become unavailable before you can book it. We suggest you book as soon as possible to not loose your favorite vacation rental. City of Sarasota Certificate VR22-00089

Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)

Listing Agent: Jennifer Le Blanc (941-400-0374)

Remarks: Booked currently for June 17th-July 5th, Nov. 22nd-Nov 29th, Dec 23rd 2026-Jan 1st 2027, March 13th-20th, March 27th-April 3rd, April 10th-17th 2027 St. Armand's Circle, the famous vacation destination in Florida, is home to this beautifully decorated 6 bedroom 4.5 bath vacation home (which includes a 1 bedroom/1 bath attached bedroom and bath off of the garage). A wonderful 2 story pool home with granite kitchen, formal dining area, wood flooring which sleeps (14). The floor plan boasts an eat-in kitchen with breakfast table and breakfast bar. The house is equipped with wi-fi and TV's in most bedrooms. The sliding glass doors lead to the gorgeous backyard featuring an outdoor pool where the sun is waiting to warm your body and spirit! City of Sarasota Certificate VR22-00148

Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)

Listing Agent: Jennifer Le Blanc (941-400-0374)

Remarks: This amazing turnkey furnished home is just steps from the sandy shores within the Lido Shores private gated beach access. A short jaunt to St Armand's Circle with about 100 stores St Armand's Circle is world known as an unforgettable destination. From vacation trinkets to upscale galleries, breakfast or lunch cafes to gourmet dinner feasts at top of the line restaurants you will find it all. Head north to Longboat Key with plenty of sidewalks for walking or biking. You will find 4 spacious bedrooms all with en-suite bathrooms plus a powder room downstairs for guests. Open-plan living room on first floor just off the fully equipped kitchen with modern appliances, breakfast bar and dining table. Living room has wood burning fireplace with sliders going out to the private, sunny patio pool area with grill and outdoor shower. Family room off the primary bedroom on 2nd floor with 53" tv and built-in shelves. Salt water pool with electric pool heater. Just bring your toothbrush and clothes to start enjoying our strong sense of leisure Florida lifestyle.

Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)

Listing Agent: Jennifer Le Blanc (941-400-0374)

Remarks: ANNUAL RENTAL IN HIGHLY SOUGHT AFTER WEST OF TRAIL LOCATION NEAR THE FIELD CLUB. MAJOR RENOVATIONS ARE COMPLETE! Updates include exterior and interior painting, impact windows and doors, porcelain tile in the living room, dining room, and primary bedroom, updated guest bathrooms, updated landscaping, new outdoor kitchen grill, new refrigerator, and more. The open concept kitchen and family room overlook enclosed brick lanais and mature trees and landscaping—the perfect place for entertaining. The master bedroom and office are located on the first floor. The remaining bedrooms and game room are located upstairs—a perfect layout for guests/family. The screened patios with outdoor kitchen overlook the saltwater heated pool. The neighborhood has a brand new deeded boardwalk and fishing pier—a great place to launch a kayak or for boat pick ups/drop offs. The central location makes for a quick drive to Siesta Key, Downtown Sarasota, dining, and shopping.

Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)

Listing Agent: Alex Lane (941-960-3080)

Remarks: Welcome to the Ringling Retreat, a luxurious family compound in the heart of downtown Sarasota. The property sits just a few blocks from the East end of Main Street downtown and is perfectly walkable to the Legacy Trail, Payne Park, & a number of shops & restaurants. A screened entryway in the front greets you before stepping through the front door into a light and bright living area with views out to the new heated pool & generous seating including a queen sleeper sofa & two club chairs. A 65 inch mounted tv in this room w/ complimentary streaming services is accessible from the living room as well as the 3 stools at the breakfast bar separating the living space from the designer kitchen. The kitchen offers SS appliances & European style cabinets that are all labeled for your convenience & offer soft close hardware. Adjacent to the kitchen is a large dining area with seating for up to 12. The main house offers 3 large bedrooms & 2 well appointed bathrooms. The bed configuration is as follows: Bedroom 1 is just off the living room and is separated by french doors with privacy curtains. This room offers sleeping for up to 4 guests w/ two stand alone twin beds as well a twin over twin bunk bed. An open shelf closet, nightstand and mounted tv complete the set up. Bedroom 2 is located on the Master wing of the house with good separation from the Master bedroom and with easy access to the guest bathroom. This room offers a queen bed with two nightstands, a dresser and a large reach in closet. A large flat screen tv sits on top of the dresser. The Master bedroom is huge and offers a king bed with two nightstands, a dresser and a mounted tv on one of two shiplap accent walls. The Master has a zen feel and offers a large walk in closet, separate water closet/toilet area, and a recently remodeled spa-like bathroom with tiled shower, and double vanity sinks. Access to the courtyard & pool area is available from the Master. Step beyond the kitchen & dining area to an exterior covered breezeway to find a laundry closet to the right as well as a beach essentials closet to the left. The keypad enabled door between both closets grants access to the guest house which features a full living room w/ two large sofas including a queen pullout sleeper sofa as well as two club chairs. Adjacent to the living area is a full kitchen & eat-in kitchen area as well as a 2nd washer & dryer. Beyond the living space is a large bedroom w/ King bed, 2 night stands & mounted flat screen. This 2nd Master offers a walk in closet & full en suite bathroom. Beyond the breezeway & into the courtyard you'll find a large glistening pebble tec heated saltwater pool w/ an in-ground heated spa and large sun shelf that allows you to stay dry with your toes in the water. Two in-pool club chairs offer cupholders for your cold beverages as you soak up the Sarasota sunshine. Need some shade? We installed a Miami Dade hurricane rated patio with covered roof and an outdoor kitchen and bar area offering ample counter space and cabinetry, a mini fridge, and a premium 40" propane grill. 4 stools face the mounted TV so you can watch the game while your loved ones play nearby. Outdoor dining can be had either at the outdoor kitchen bar or the dining table with seating for 8 under a teal Sunbrella. On the far side of the pool you'll find a gorgeous putting area for golf enthusiasts and children alike. New landscaping and landscape lighting make this feel like a resort at night.

Listing is courtesy of: UPTOP REAL ESTATE SERVICES, LLC (941-554-4896)

Listing Agent: Adam Kabinoff (941-554-4896)

Remarks: Park your Boat behind your home .... Welcome to this boaters paradise! This recently renovated 3-bedroom, 3-bathroom home nestled in the heart of Siesta Key. With 3,324 square feet of well designed living space, this contemporary home offers both luxury and comfort in one of Florida's most coveted locations. Step inside to find over-sized rooms that can be utilized for entertaining or simply unwinding after a day at the beach and boating. These multi-purpose rooms adapt to your lifestyle, whether you need another bedroom, home office, fitness space, or creative art studio. A true showstopper awaits outside, where a Lucas Lagoons designed pool transforms your outdoor living area into a resort-worthy oasis. Known for creating breathtaking aquatic masterpieces, this signature pool feature turns everyday swimming into a resort setting for entertainment. Imagine hosting poolside gatherings that friends will talk about for years to come! Sun worshippers will appreciate the large rooftop tanning area—your private perch for soaking up Florida's famous sunshine while enjoying gentle Gulf breezes. It's like having your own exclusive sundeck without the crowds. This house is the perfect balance between contemporary sophistication and vacation-like comfort. Beautiful, neutral finishes throughout create an atmosphere of elegance without sacrificing that relaxed coastal vibe that makes Siesta Key special. Location? Simply unbeatable. Situated in central Siesta Key, you're just a stroll from the bustling Siesta Key Marketplace where local shops and dining options abound. Siesta Market is less than a 10-minute walk away—perfect for picking up ingredients for an impromptu dinner or beach picnic. For those who appreciate the island's famous nightlife, Siesta Key Oyster Bar and Daiquiri Deck are within easy walking distance. Meanwhile, the world-renowned Siesta Beach—celebrated for its powder-fine white sand—is just a short bike ride from your doorstep. The primary bedroom offers a serene retreat after days filled with sunshine and adventure, while the additional bedrooms provide comfortable accommodations for family and guests. This isn't just a house—it's an invitation to embrace the laid-back yet luxurious Siesta Key lifestyle. Where morning coffee comes with water views, weekends blend into beach days, and every evening feels like a vacation. Why visit paradise when you can live there?

Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)

Listing Agent: Colette Jay (941-713-7711)

Remarks: Arrive. Unwind. Experience Siesta Key at its finest. Welcome to your private luxury retreat on Siesta Key, a modern sophisticated 4-bedroom, 4-bathroom home designed for elevated coastal living. Tucked away in one of the island’s most desirable locations, this residence offers the perfect blend of privacy, comfort, and effortless elegance. From the moment you step inside, you’re welcomed by light-filled interiors, thoughtfully designed spaces, and a calming, refined aesthetic, and tropical views. Each bedroom serves as a peaceful sanctuary, while four well-appointed bathrooms provide both convenience and privacy, ideal for families, couples, or executive getaways. The home is designed for seamless living with an open concept. Spacious gathering areas invite connection including a built-in deck spa, while modern amenities including climate-controlled comfort, quality linens, and everyday essentials to ensure a stay that feels both luxurious and easy. Whether you’re getting ready for an evening out or returning from a sun-soaked beach day, every detail has been considered. Spend your days exploring the powdery white sands of nearby Siesta Beach and Village, consistently ranked among the best beaches in the world, or enjoy the vibrant dining and shopping scene just minutes away in Siesta Key Village. Also, for entertainment purposes, the property is close to Sarasota and the downtown main street area. As the day winds down, return to your private retreat to relax, recharge, and savor the quiet luxury of island living. This is more than a place to stay, it’s a curated Siesta Key experience.

Listing is courtesy of: GOOD LIFE REALTY LLC (941-342-9889)

Listing Agent: Raffilena Hamilton (941-685-2441)

Remarks: Available : 2026: Open September 1 through November 15th 2027 - 30 Day Minimum Stay... 2027: Peak Season Now Open for January and April. February and March are not available.. Experience the best of Siesta Key living with private beach access—this expansive, exceptional home offers everything needed for the perfect coastal escape. Thoughtfully designed indoor and outdoor living spaces create comfort and privacy even when hosting a full house. Each bedroom, along with the main living area, opens to its own deck, providing the perfect spot to savor morning coffee, unwind with a book, or soak up the sunshine. A custom heated pool and spa add to the home’s private resort feel, while tasteful updates throughout make it a serene coastal get-away. Nestled on a quiet dead-end street—one so tucked away that even many locals don’t know it exists—this rare gem defines beachfront living at its finest. It’s a unique opportunity to claim your own slice of paradise. Just steps from the powder-soft sands of Siesta Key, with deeded beach access leading directly to Turtle Beach, this home places the island’s most coveted amenity right at your doorstep. Whether you're heading out for peaceful morning walks, unforgettable sunsets, or the convenience of a close-by spot for all your beach gear, this residence offers the ideal home base for your dream coastal getaway. Taxes and fees apply to base rent..

Listing is courtesy of: SHOWTIME REALTY (941-822-0890)

Listing Agent: Robert D. Bevington (412-671-3142)

Remarks: Welcome to your dream escape on Siesta Key—a completely reimagined coastal retreat designed to make every moment unforgettable. Tucked away on a quiet stretch of Avenida de Parasido, this stunning 3-bedroom, 2-bath home has been fully remodeled from top to bottom with brand-new, designer furnishings. Everything is fresh, pristine, and waiting, be among the very first to experience it. Step inside to an airy, light-filled space where coastal elegance meets effortless comfort. The open layout invites connection—whether you’re sharing meals, relaxing after the beach, or simply enjoying the calm of your surroundings. Out back, your private oasis awaits. A secluded yard wraps around a sparkling pool, creating the perfect setting for morning coffee, sun-soaked afternoons, or quiet evenings under the stars. It’s your own slice of paradise—peaceful, private, and entirely yours. Location is everything—and this one is unbeatable. You’re just steps from the heart of Siesta Key Village, where vibrant local life unfolds. Discover eclectic restaurants loved by locals, charming boutiques unique to Sarasota, live music drifting through warm evenings, and an energy that’s both relaxed and alive. And then there’s the beach. Just moments away lies the world-famous Siesta Key Beach—renowned for its powdery white quartz sand and the crystal-clear waters of the Gulf. Whether you’re swimming, sunbathing, or catching a sunset that feels almost unreal, this is coastal living at its finest. When you’re ready to explore beyond the island, downtown Sarasota is only minutes away. Immerse yourself in a thriving arts scene with live theater, ballet, multiple orchestras, and an impressive collection of galleries. Food lovers will appreciate the exceptional dining culture—this area boasts one of the highest concentrations of top-rated restaurants per capita in the country. This isn’t just a place to stay, it’s where beach days, vibrant nights, and total relaxation come together effortlessly. All that’s missing is you.

Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)

Listing Agent: Beth Dilley (941-400-1322)

Remarks: Welcome to your perfect island getaway at 301 Avenida Madera #B, ideally located in the heart of Siesta Key—this is truly THE location! Just steps from popular spots like Village Cafe and The Hub Baja Grill, and only a short walk to the world-famous Siesta Key Beach, this beautifully updated 2-bedroom, 2-bath home offers the perfect blend of comfort and coastal charm. Inside, you’ll find a bright open floor plan with a relaxed coastal theme, a fully equipped kitchen featuring granite countertops, stainless steel appliances, and a Keurig coffee maker, plus a spacious dining area overlooking a peaceful canal. The home comfortably sleeps up to 6 guests with a queen-size sofa bed and an auto-inflatable queen EZ bed, while the primary suite includes a private full bathroom. Step outside to enjoy true Florida living—grill out, swim, sunbathe, or fish right from the canal, and don’t forget your furry companions as this property is extremely pet-friendly. The shared pool area (with Unit A) adds to the experience, while both units has private entrances with no shared interior walls, ensuring added privacy. For peace of mind, exterior security cameras are in place, and the unit is strictly smoke-free with no indoor smoking permitted. Whether you're walking, biking, or taking the trolley to Siesta Key Village, everything you need is within reach—making this an exceptional opportunity to enjoy the ultimate Siesta Key lifestyle.

Listing is courtesy of: SHOWTIME REALTY (941-822-0890)

Listing Agent: Robert D. Bevington (412-671-3142)

Remarks: If you’re searching for the perfect location for your next vacation, your search ends here! This beautifully updated 2-bedroom, 2-bath home is ideally situated in the heart of Siesta Key, within Siesta Key Village and just a few blocks from the world-famous Siesta Key Beach. Designed with a bright coastal theme, the home features an inviting open layout and a fully updated kitchen with solid surface countertops, stainless steel appliances, and a charming breakfast nook. The spacious primary suite offers a king-sized bed and a private en suite bathroom with a walk-in shower. A standout feature of this home is the private rooftop deck, complete with outdoor furniture, a grill, and umbrellas for shielding the sun- perfect for enjoying sunny afternoons or relaxing evenings while taking in stunning sunset views over Siesta Key Beach. During the day, enjoy the convenience of walking to the beach, local shops, and restaurants, or take a short drive over the bridge into Sarasota for even more dining, shopping, and entertainment options. This pet-friendly home is ideal for family gatherings, and for larger groups, Unit B can also be rented for additional space. The pool area is shared with the neighboring unit, while both units maintain privacy with separate entrances and no shared interior walls. The home is strictly smoke-free with no indoor smoking permitted. Enjoy your stay in this exceptional island retreat!

Listing is courtesy of: SHOWTIME REALTY (941-822-0890)

Listing Agent: Robert D. Bevington (412-671-3142)

Remarks: Listing reflects peak season rate. Welcome to Leona's Retreat, a beautifully renovated, ground-level bungalow perfectly poised on the intercoastal canal waterway. This charming home offers the ultimate blend of peaceful island living and convenient access to all that Siesta Key has to offer. Step inside to a bright, coastal-styled haven designed for relaxation and comfort. The spacious primary bedroom features a plush king-size bed and a bathroom across the way, providing a private sanctuary. Two additional bedrooms offer flexible sleeping arrangements: one with a comfortable king-size bed, and the other ideal for families with a double bed and a single bed. You'll find a full kitchen stocked with all the essentials, plus a convenient washer/dryer to make your stay effortless. Outside, your expansive, private backyard is a true highlight. Take a refreshing dip in the private heated pool, unwind in the bubbling hot tub, or simply lounge in the ample space for sunbathing and outdoor dining. With direct access to the intercoastal canal, you can enjoy quiet moments fishing or watching the tranquil tides. Leona's Retreat boasts a truly prime location on a quiet, family-oriented street. You're just a delightful five-minute stroll to the vibrant Siesta Key Village, brimming with charming shops, delectable restaurants, and lively entertainment. And for those iconic beach days, the world-famous Siesta Key Beach is only a ten-minute walk away! We've ensured you're perfectly equipped for a memorable day by the sea. The home includes all the beach day essentials: beach chairs, beach towels, coolers, frozen ice packs, and a convenient cart to easily tote everything down to the sand. Ready to experience the best of Siesta Key? Book your unforgettable stay at Leona's Retreat today!

Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)

Listing Agent: Beth Dilley (941-400-1322)

Remarks: This is a short term rental. Listing reflects peak season rate. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kids downstairs and a relaxing haven for adults upstairs. No need to fight over the king-size bed, as this home boasts two luxurious king-size bedrooms! Both offer comfortable retreats and easy access to your private pool, perfect for a refreshing dip anytime. The third bedroom features a trundle bed that comfortably sleeps two. Outside, the private pool area awaits with lounge chairs for sunbathing, an outdoor shower, and a delightful area to grill and enjoy alfresco dining at the table for six. Just moments away, the vibrant energy of Siesta Key Village, with its diverse culinary scene and local shops, offers endless opportunities for exploration. Surf's Up provides the ideal launchpad for experiencing all that Siesta Key has to offer, with plenty of room to relax and recharge in between adventures. Perfect for families seeking sun, relaxation, and easy access to Siesta Key Beach & Village. Book your unforgettable getaway now! Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation.

Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)

Listing Agent: Beth Dilley (941-400-1322)

Remarks: Experience the perfect blend of comfort, elegance, and convenience in this stunning turnkey furnished 4-bedroom, 3.5-bath modern vacation home. Thoughtfully designed to accommodate up to 10 guests, this property offers the ideal setting for families, friends, and luxury vacationers seeking a private oasis close to everything Sarasota has to offer. Step inside to find a spacious open floor plan with sleek finishes and top-of-the-line appliances, including a Subzero refrigerator and Wolf induction cooktop—perfect for creating memorable meals. Multiple indoor and outdoor dining spaces make entertaining effortless, while the comfortable living areas provide plenty of room to unwind. Outdoors, enjoy resort-style living on a double lot with a large fenced yard. Spend your days lounging by the sparkling pool and spa, grilling, rinsing off in the outdoor shower, or soaking up the Florida sunshine on the chaise lounge chairs. This home is ideally located—just steps to the Legacy Trail for biking and walking, only 1 mile from vibrant Main Street with its shops, cafes, and nightlife, and a short drive to Sarasota’s award-winning white sand beaches. Whether you’re looking for adventure, relaxation, or world-class dining, this home offers it all. Make your stay unforgettable in this modern luxury retreat designed for both relaxation and connection. *weekly rates available* Not Available Jan 13 2026- April 16 2026. Not Available April 25 2026- May 02 2026. Not Available May 10 2026- May 17 2026. Not Available July 11 2026- July 18 2026. Not Available February 13 2027- March 4 2027.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Rinat Sikdar (941-993-9292)

Remarks: Charming Lido Shores beach cottage steps from residents’ private gated white sand beaches and crystal blue waters of the Gulf of Mexico. Lido Shores is renowned for many Sarasota School of Architecture masterpieces and waterfront estates. Westway Drive is home to some of the city's most fashionable and expensive properties. This 3/3 furnished home (with many signature pieces from "The Sarasota Collection Home Store") is Canopied by a lush mango tree, with a tranquil and tropical setting. Enjoy the spacious backyard and a large 400+ sq ft screened-in front lanai that’s ideal for morning yoga and even better for evening cocktails. From the bright entry is a spacious dining room with an open-concept kitchen with countertop space and seating. Beyond the kitchen, is a spacious open dining and living area. The bedrooms are thoughtfully laid out to preserve privacy and ensure plenty of room with private baths. The largest suite has a queen bed, and a dedicated office with a comfy chair & TV. The front bedroom has a king bed and welcomes light from a set of French doors that open directly to the screened Lanai. The third bedroom has a queen bed and access to the guest bath. This stylish home is located in the heart of Lido Shores. St. Armands Circle is located less than a mile away, providing world-class shopping and dining.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-957-3730)

Listing Agent: Valarie Wadsworth (941-780-3858)