Vacation Rentals By Owner In Sarasota, FL

5213A Calle Menorca - Book your next getaway just steps away from all that Siesta Village has to offer! 5213 A Calle Menorca is one of four condos, on the property, in the heart of Siesta Key, FL. This is a first floor unit. The interior is beachy, comfy, cozy and the exterior feels like a resort with two new pools and a tiki bar. Make your reservations fast because these will not remain available for long, especially in prime season. brbrBedroom 1-1 King Bed (Sleeps 2)brBedroom 2-2 Twin Beds (Sleeps 2)brbrTHE SIESTA BEACH RENTALS ADVANTAGE brbrAll photos, calendar dates, and rates on this website are 100% accurate. All of our homes include cable TV, Wi-Fi, quality linens, beach towels, chairs and umbrellas. Our kitchens are stocked and include pots, pans, plates, silverware, glasses, coffee mugs and other items. The unit is supplied with some basic household needs (starter roll of toilet paper and paper towel one garbage bag). SBR does not supply toiletries, hair dryer, iron or ironing boards during your stay. brbrWe make it easy to stay with us! Drive straight to your rental and access the home with your unique lock code. We will send you detailed check-in instructions 48 hours prior to arrival, and we are available 24 hours a day with live help should you require it. brbrSiesta Beach Rentals follows local/state tax rules. Each reservation includes applicable taxes and fees.brbr*Taxes & Fees not included.br*Check In / Check Out-Strictly Saturday to Saturday during Prime season. Call directly to negotiate options during Summer and Winter seasons.br*Prime Season rates may apply for certain holidays.

Pet Friendly Condo w/ Newly Updated Pool and Interior, Five Minute Walk to Beach

Sarasota, Florida, United States

Bed

Bath

Sleeps

$334.75

5209B Calle Menorca - This is the vacation you've been waiting for! 5209 B Calle Menorca is one of four condos, on the property, in the heart of Siesta Key Village. This is a second floor unit and requires climbing stairs. The interior is tastefully furnished with a bright beachy feel and the exterior feels like a resort with two pools and a tiki bar. Make your reservations fast because these will not remain available for long, especially in prime season. brbrBedroom 1-1 King Bed (Sleeps 2)brBedroom 2-2 Twin Beds (Sleeps 2)brbrTHE SIESTA BEACH RENTALS ADVANTAGE brbrAll photos, calendar dates, and rates on this website are 100% accurate. All of our homes include cable TV, Wi-Fi, quality linens, beach towels, chairs and umbrellas. Our kitchens are stocked and include pots, pans, plates, silverware, glasses, coffee mugs and other items. The unit is supplied with some basic household needs (starter roll of toilet paper and paper towel one garbage bag). SBR does not supply toiletries, hair dryer, iron or ironing boards during your stay. brbrWe make it easy to stay with us! Drive straight to your rental and access the home with your unique lock code. We will send you detailed check-in instructions 48 hours prior to arrival, and we are available 24 hours a day with live help should you require it. brbrSiesta Beach Rentals follows local/state tax rules. Each reservation includes applicable taxes and fees.brbr*Taxes & Fees not included.br*Check In / Check Out-Strictly Saturday to Saturday during Prime season. Call directly to negotiate options during Summer and Winter seasons.br*Prime Season rates may apply for certain holidays.

Amazing Pet Friendly Condo w/ Pool a Block to Siesta Key Village, Newly Updated

Sarasota, Florida, United States

Bed

Bath

Sleeps

$160.62

Beautiful one bedroom 1.5 bathroom apartment. Located few min away from Sarasota downtown , St. Armand circle and Lido beach. Gated community offers gym and outdoor pool. .

Apartment

Cozy 1-bedroom apartment in pleasant Sarasota with WiFi, AC, fitness room

Sarasota, Florida, United States

Bed

Bath

Sleeps

$262.99

Freshly remodeled spacious house to gather with friends or family.A lovely space to unwind and relax after a busy day at the beach or visiting places. Awake refreshed and ready for a day exploring the city via this clean, sunny house. Head out and wander through the nearby parks and beaches.brFully stocked kitchen, free parking , Tesla EV charger, Hot tub, playground area, firepit, wifi, boardgames and more.

Relax and recharge Hot Tub,Tesla charger,10 sleeps

Sarasota, Florida, United States

Bed

Bath

Sleeps

$330.15

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrCoral Breeze – Modern Comfort with Year-Round Pool & Sunroom brbr brbrYour Sarasota getaway starts here! Coral Breeze is a stylishly remodeled 3BR/2BA home in the quiet Gulf Gate neighborhood, just a short drive to world-famous Siesta Key Beach. Dogs are welcome with approval, making it easy to bring your furry friend along for the adventure. brbr brbrLOCATION HIGHLIGHTS: brbr-Located in the quiet Gulf Gate neighborhood of Sarasota brbr- Just a short drive to Siesta Key Beach, consistently ranked among the best in the U.S. brbr- Close to shopping, restaurants, and local conveniences while maintaining a peaceful residential feel brbr brbrPROPERTY FEATURES: brbr- 3 bedroom/ 2 bathroom pool home (1529sq ft) brbr- Large heated pool (optional heating fee) brbr- Fully fenced backyard for privacy and pet safety brbr- Dog-friendly with prior approval brbr brbrLIVING ROOM: brbr- Spacious, open living area with a large L-shaped sectional sofa brbr- Big-screen Smart TV for relaxing movie nights brbr- Bright, airy layout with large windows and natural light brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with modern appliances and cookware brbr- Open-concept design ideal for socializing while cooking brbr- Dining table with seating for six guests brbr brbrBEDROOMS AND BEDROOMS: brbr- Master bedroom: king bed, dresser with mirror, closet space brbr- Master ensuite bathroom: walk-in shower with glass door, vanity with backlit mirror brbr- Guest bedroom #1: queen bed, dresser with mirror, closet space with mirror doors brbr- Guest bedroom #2: queen bed, dresser with mirror brbr- Guest bathroom: tub/shower combo with glass doors, vanity with backlit mirror brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach wagon, beach umbrella and beach towels brbr brbrLOCAL FAVORITES: brbr- Siesta Key Beach – world-renowned white sand and turquoise waters brbr- Gulf Gate Village – local shops, bars, and restaurants just minutes away brbr- Legacy Trail – nearby biking and walking path brbr- Downtown Sarasota – dining, arts, and entertainment less than 20 minutes away brbr brbrIMPORTANT INFO: brbr- Pool heat available for an optional fee brbr- Dogs allowed with approval (fee may apply) brbr- No smoking or vaping permitted inside the home brbr- Quiet residential neighborhood – no parties or large gatherings brbr brbrWHETHER YOU’RE HERE FOR A FAMILY GETAWAY, A SEASONAL ESCAPE, OR A COUPLES’ RETREAT, CORAL BREEZE OFFERS THE PRIVACY OF A RESIDENTIAL NEIGHBORHOOD WHILE BEING JUST A SHORT DRIVE FROM THE AWARD-WINNING SANDS OF SIESTA KEY BEACH.brbrAll pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs.brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

Relax in style at Coral Breeze! Your private Sarasota escape | Heated pool | Sunroom | Dog-friendly

Sarasota, Florida, United States

Bed

Bath

Sleeps

$282.61

Located JUST 2 miles off Siesta Key beach! Bikes, beach gear, and more included: tea & coffee, shampoos, conditioner, included with your stay. Head over to your favorite white sandy beach spot on Siesta Key, or stroll a block away to Gulf Gate - a Mecca of shopping and Restaurants for every pellet! Enjoy Vegan, Raw, Sushi, BBQ, Craft Bear, Italian... and more. Large updated fully equipped kitchen with ice maker, French press, Keurig, or drip, pots/pans, microwave, full sized oven range with glass cooktop. Cozy beds, (Serta & Sealy) Screen Porch & private backyard. Bonus 2.5 Bathrooms! Bookings over 8 guests- ask if we cdd can accommodate before booking. brbrBeach Gear: Bikes, Towels, Chairs, Coolers and umbrella.

Portal to Everything - Siesta Key & Beyond :-)

Sarasota, Florida, United States

Bed

Bath

Sleeps

$709.38

Welcome to Picasa by Stayawhilewithus — a Mediterranean-style 5BR/4BA golf-front retreat, on over an acre in one of Sarasota’s most desirable locations. Minutes to Siesta & Lido Key Beaches, Downtown Sarasota, St. Armands’ Circle, and SRQ. Enjoy a resort backyard with a resurfaced heated pool & spa (in Oct. 2025), a pickleball court, and a fire pit, in addition to elegant interiors with a chef’s kitchen, game room, and spacious bedrooms for families, golf groups, and wedding guests.brbr✦ The Space ✦brbrLocation meets luxury at Picasa, set in one of Sarasota’s most desirable spots. Just minutes to Siesta Key and Lido Key beaches, Downtown Sarasota, St. Armands Circle, and SRQ Airport, this retreat keeps you close to the best dining, shopping, golf, wedding venues, and cultural attractions.brbrLocated on over an acre of land, the backyard feels like your own private resort. Relax in the heated pool & spa (resurfaced in Oct 2025), play on the full-size pickleball court, or gather around the fire pit with sweeping views of Sara Bay Golf Course and the tranquil waters of Bowlees Creek. Expansive outdoor living areas, a Mediterranean-style courtyard, and a covered lanai with shuffleboard create the perfect setting for relaxation and connection.brbrInside, elegant designer touches flow through the open-concept living areas, chef’s kitchen with two refrigerators, and a game room with arcade and foosball. With five spacious bedrooms and four bathrooms — including multiple ensuites — Picasa is designed to host families, golf groups, and wedding guests in style and comfort.brbr✦ Why Guests Love Picasa ✦brbr✅ Prime Sarasota Location – Minutes to Siesta Key, Lido Beach, Downtown Sarasota, St. Armands Circle, and SRQ Airport — close to beaches, golf, shopping, dining, and top wedding venues.brbr✅ Resort-Style Backyard on Over an Acre – Heated private pool & spa (resurfaced in Oct 2025), full-size pickleball court, fire pit, BBQ grill, Mediterranean-style courtyard, and a covered lanai with shuffleboard — your own private resort oasis.brbr✅ Golf-Front Views – Nestled along Sara Bay Golf Course with tranquil views of fairways and Bowlees Creek.brbr✅ Designer Interiors & Game room – Mediterranean-inspired style paired with a game room featuring arcade games and foosball.brbr✅ Spacious 5BR/4BA Layout – Multiple ensuites make mornings and evenings stress-free for families and groups.brbr✅ Luxury Kitchen – Modern appliances and 2 full-size refrigerators, perfect for weddings, snowbirds, or extended stays.brbr✅ Family-Friendly & Pet-Friendly – 2 Pack ’n Plays, kid dinnerware, washer/dryer, plus bring your furry friends along.brbr✅ Beach Essentials Included – Chairs, umbrellas, a wagon, and towels make trips to the sand easy.brbr✅ Fully Stocked for Comfort – Toiletries, detergents, paper goods, and more are always provided.brbrbr✦ Where You’ll Sleep ✦brbr- Master Suite – King bed • Workspace • Ensuite bathbr- Bedroom 2 – King bedbr- Bedroom 3 – Queen bedbr- Bedroom 4 – 2 Full bedsbr- Bedroom 5 – 2 Twin-over-Full bunks • Ensuite bathbrbr✦ Kitchen ✦brbrCook, bake, or entertain with:brbr- Espresso & Drip Coffee makers (coffee/sugar provided)br- 2 full-size refrigerators — great for groups & weddingsbr- Blender, lobster pot, bakeware, cookwarebr- Microwave, toaster, kettle, dishwasherbr- Place settings & kid-friendly dinnerwarebrbr⭐ Location Highlightsbrbr- The Ringling Museum of Art – 3.8 mibr- Asolo Repertory Theatre – 3.9 mibr- Sarasota Bradenton Intl Airport (SRQ) – 4.3 mibr- Sarasota Jungle Gardens – 5.2 mibr- Sarasota Opera House – 7.3 mibr- Downtown Sarasota – 7.9 mibr- UTC Mall – 9 mibr- St. Armands Circle – 9.4 mibr- Nathan Benderson Park – 9.7 mibr- Lido Key Beach – 10.2 mibr- Mote Marine Aquarium – 10.9 mibr- Lakewood Ranch Sports Complex – 13.4 mibr- Siesta Key Beach – 14.3 mibrbr Nearby Wedding Venues!brbr- Powel Crosley Estate – 3.6 mibr- The Ringling / Ca’ d’Zan – 4.2 mibr- The Ritz-Carlton Sarasota – 7.2 mibr- Marie Selby Botanical Gardens – 8 mibr- Sarasota Yacht Club – 9.2 mibr- Laurel Oak Country Club – 17.8 mibrbr⛳ Golf & Country Club Highlights!brbr- Sara Bay Golf Course – 1.6 mi (Donald Ross–designed, private)br- Palm Aire Country Club – 5.7 mi (private, 36 holes + tennis)br- University Park Country Club – 8.6 mi (private, 27 holes + pickleball)br- Bobby Jones Golf Club – 9.6 mi (public)br- Village Green Golf Club – 12.1 mi (public, executive course)br- Tatum Ridge Golf Links – 14.9 mi (public, links-style)br- The Founders Club – 15.9 mi (luxury private club)brbr✦ Book Your Stay ✦brbrFrom sun-soaked beaches and world-class golf to family gatherings and wedding weekends, Picasa is your private haven in Sarasota. Here, a prime location meets a resort-style backyard and Mediterranean design — all crafted for unforgettable memories.brbr✨ Book your stay at Picasa today and experience Sarasota’s best, from luxury at home to adventure at your doorstep.brbr⭐ Pet Friendly!brbr- Prior approval is kindly required. We allow up to 3 dogs.br- $200/stay/first pet, $100/stay/second pet, $100/stay/third pet.br- Must be fully house-trained.br- Must be completely cleaned up after.br- Leashed at all times when not in a fenced area.br- Crated indoors when not home with the pet.br- If barking becomes an issue during your stay, alternative arrangements must be made.br- Not allowed on indoor furniture, bedding, or in the pool or spa.brbrKindly Note!brbr- For your peace of mind, surveillance cameras are located around the exterior of the house (located by the front door, the side courtyard and by the pool equipment). No inside cameras, and none overlooking the pool and spa.brbr- Noise monitors inside and outside the house do not record voice or conversation, they only monitor decibels.brbr- The pickleball court size is 20 ft. x 44 ft.brbr- We provide free parking on the premises (our driveway can fit up to 5 cars).brbr- BBQ Grill and an empty extra propane tank are provided. Guest are responsible for exchanging the propane tank at the local stores for use.brbr- The heated pool feature is available for an extra $20/night or $400/month (offered from October till May). If you would like to purchase the pool heating feature, please note that it covers the entirety of your stay, and the pool heater may take up to 48 hours to reach the desired temp, so kindly let us know a week before you check-in.brbr- Pool settings are all scheduled. When booked, pool heat is set to 85 degrees, however, pool temps are impacted if the weather drops below 60 degrees. So, unfortunately, pool temperatures cannot be guaranteed.brbr- For your comfort, our home is treated quarterly by a professional pest control company. But given our tropical climate, you may still see the occasional bug. Please keep doors and screens closed to help prevent bugs from entering, as no compensation will be provided for any bugs that may come inside.brbr- Liability/Risk: The hosts/co-hosts are not responsible for any accidents, injuries or illness that occurs while ON or OFF premises while using equipment provided as part of the rental, including but not limited to pool, spas, stairs or playsets. By accepting this reservation, it is agreed that all guests are expressly assuming the risk of any harm arising from their use of the premises and equipment taken off the premises. This also applies to others whom the guest invites to use the premises or equipment.brbrIMPORTANT NOTE: For the security of our guests, every guest who enters the home during your stay MUST be listed on the reservation or disclosed to the host. Please, make sure to register the correct number of guests. Undisclosed guests who are not included in the official confirmation can place your stay at risk for early termination without a refund, and can incur an additional charge of $25/guest.

5BR/4BA |Pool & Spa + Pickleball, Golf View

Sarasota, Florida, United States

5

Bed

4

Bath

14

Sleeps

$239.93

The most desirable location in downtown Sarasota, this 1/1 condo overlooks Main Street and is a short stroll to Marina Jacks, downtown shopping and restaurants as well as The Sarasota Opera House. St Armand's Circle restaurants and shops and Lido and Siesta Key beaches are minutes away. The buildling offers 24 hour concierge, secure parking garage (fee), exercise room and pool/spa available as well as a social room with pool/library. This building requires a 3 month minimum stay and an application fee and a building security deposit. No pets. Available August 2023 through December 2023. Not avail J-M 2024. Note: Summer/Fall rental periods, guest pays electric bill over $100/month.

Desirable Downtown Sarasota! On Main Street walk out to restaurants/shops/shows!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$378.55

Still some limited availability for 2025 and 2026! Your Sarasota / Lido Key Oasis awaits! Newly painted and redecorated spacious Beachfront condo on 7th floor with picturesque views of Sarasota Bay and skyline. Approximately 2000 sq ft, recently furnished by new owners with decorator touches, this condo has it all! 2 bedrooms, 2 bathrooms, plus den with full size futon, sleeps 6. Lots of windows bring in natural light and beautiful views of the city. Enjoy watching sunrise from the many windows and sunset from the beach or poolside patio. brbrSpacious Master Bedroom with King bed, ensuite bathroom has oversized shower and walk in closet, and private enclosed lanai with views of the city. Guest Bedroom has Queen bed and walk in closet. Full bath with shower. Den has TV & futon for sitting, relaxing or sleeping, and desk for writing or working remotely from home. Fully appointed kitchen includes cooking basics and appliances, beverage/wine mini fridge, full size refrigerator, microwave/wall oven, Wolff cooktop and many extras for preparing your own meals. Full size dining area has extendable table that seats 6 comfortably and a spacious open living room with smart tv, sectional sofa and accent chairs, offers ample seating. An enclosed lanai with 2 ceiling fans and breakfast table with chairs, completes the living area. brbrWalking distance to Ted Sperling Nature Park, where you can walk along the south end of Lido Key on the beach and among the mangroves, or explore the water by kayak. Enjoy our private heated pool with patio and barbecue grill and our private beachfront, or walk northward up the beach to the many resorts along the Gulf for lunch along the gulf and a short walk further to the public Lido Beach. Visit the many shops and restaurants at Saint Armand’s Circle, just a short car ride away or a free trolley ride with trolley stop right in front of the building.

Sarasota - Lido Key Beachfront condo. New Listing recently redecorated.

Sarasota, Florida, United States

Bed

Bath

Sleeps

$379.33

This is a unique listing; please read the description in full before booking!brbr- Located in a quiet Sarasota neighborhood on a dead end street close to shopping, restaurants, and Siesta Key (and several other beaches within a 15m drive), this amenity packed home is perfect for families and beach goers!br- Enjoy the heated pool and brand new luxurious outdoor furniture in your fenced in backyard where you can bask in the sun swimming and grilling.br- Beautifully remodeled coastal themed interior w/ fully stocked kitchen, new appliances, Smart TVs w/ popular streaming services included in all rooms, and fast reliable WiFi. br- On site washer and dryerbr- My goal is to provide as much value and convenience to guests as I can. Beach essentials and accessories, activities for children such as board games, puzzles, and coloring books, and various baby items are just some of the additional things that I provide for guests.br** Your friendly on-site host lives in the attached mother-in-law suite and is available if needed to assist with making your stay enjoyable and worry free. I have been an AirBnB Superhost for 3 years in a row and heavily prioritize my guest's privacy during their stay. br- Outdoor space is technically shared because my entrance is through the back, however as mentioned I do place an emphasis on giving my guests space and privacy when they are utilizing the pool area. I do ask guests to confirm in their booking message that they understand the shared outdoor spaces on the listing.

☀Coastal Gem☀Heated pool & amazing location!☀

Sarasota, Florida, United States

Bed

Bath

Sleeps

$171.91

Lido-Key- Newly remodeled TINY Studio. 7-10 min walk to the beach and St.Armands Circle. Quaint main floor studio in a great location. This is an affordable way to enjoy this popular area. One of the top beaches in the U.S. This cozy cottage features a Queen bed, refrigerator, stove, microwave, coffee maker, fully stocked cooking items & dishes, along with beach chairs, and beach towels. Located at 170 Roosevelt Dr., SarasotabrThe space:brStudio is tiny, yet roomy for 2 people. Completely remodeled.brGuest access:brWe have an on-site heated pool for the condo complex to use. On-site free parking for guests.brOther things to note:brWe offer beach chairs and beach towels. Also, behind our complex is kayak rental. Bike rental within 2 blocks. VEO e scooter rentals found throughout the area. The Beach is a 7-min walk and there are 2 public access points.brbrThe location is amazing, but our vintage building was built in the 50’s, so keep that in mind so that your not expecting a brand new complex. Updates are always on-going. Our studio is small, yet comfortable.brbr**NO Children & NO Electric Car Usage on complex allowed**

Apartment

Lido-Key, New Tiny Cute Studio-E

Sarasota, Florida, United States

1

Bath

2

Sleeps

$301.69

Casa Cocoanut - Entire PropertybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrVR24,00042 / VR24,00034 - Sarasota City VRLbrbrTake advantage of a convenient central location just 12 walkable blocks north of downtown at this beautifully renovated duplex—snowbird friendly and ideal for traveling nurses, doctors, or parents visiting students. Whether you're in town for work, school visits, or a relaxing Florida getaway, this single-level home offers everything you need for a comfortable, extended stay in Sarasota.brbrEnjoy your own enclosed patio area for private outdoor dining and unwinding. Inside, the two pristine units feature updated interiors, stylish coastal décor, and all-new furnishings. The fully equipped stainless steel kitchens include all major appliances, making home cooking and cleanup easy. Pub-height dining tables are perfect for meals or family game nights, while shaded tables on the patio provide a lovely setting for alfresco dining or happy hour.brbrBoth units come with smart TVs for streaming your favorite channels using your own accounts, and inviting seating areas for relaxing after a day of exploring. Home essentials like central air-conditioning, complimentary high-speed internet, and a shared washer/dryer add extra comfort and convenience during your stay.brbrSRQ Airport and several iconic Sarasota landmarks—including Ca' d'Zan and the John and Mable Ringling Museum of Art—are just three miles away. For a beach day, head just four miles to St. Armands Circle and Lido Beach, or make a short drive to the famous white sands of Siesta Beach.brbrJust one block from the property, Pioneer Park offers a public tennis court, a playground, and several historical sites—perfect for family outings. You can also walk to the Van Wezel Performing Arts Center to enjoy live performances, concerts, and Sunday movies in the park. Explore vibrant Downtown Sarasota, with its tree-lined streets, dining spots, shops, and waterfront parks like Bayfront Park and Marina—great for relaxing, strolls with your pup, or watching boats drift by on the bay.brbrWhether you're here for a season, a few weeks, or just a weekend, this comfortable, centrally located home invites you to experience the best of Sarasota with ease and style.brbrThings to KnowbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 6 vehicles.brbrDock details: less than 2 block nearby city boat dock.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Dog-friendly, renovated duplex with two kitchens, washer/dryer, & patio

Sarasota, Florida, United States

Bed

Bath

Sleeps

$319.18

Fantastic vacation spot with a luxurious screened in private pool - this spacious house has all the amenities of home so you'll never want to leave! Just a quick 5 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St Armand's Circle with tons of shops and restaurants! brbrThe Master bedroom has a king-sized bed with private access to the patio and pool. The other 2 bedrooms are located in a separate wing of the house, and they share a bathroom and their own pool access. Located on a quiet street with friendly neighbors, close to the mall, grocery store, and anything else you might need. We've owned this house for 10 years, and we absolutely love the area.

Vacation Paradise Close to Beach!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$493.17

Charming Bayfront Home in heart of Siesta Key. 3 bdrm/3.5 bath, full water views, spectacular sun rises, private, gas heated pool, boat dock and outdoor sitting area in lush tropical landscape. Open floor plan, contemporary decor, gas fireplace, hardwood floors throughout, updated kitchen, stainless steel appliances, granite counters and a full walk-in pantry. 2 Master Suites upstairs and one guest bdrm on main floor. 1 car garage, washer and dryer inside, 3 TV’s. Outdoor shower. Pier with boat dock; great for fishing.

True Island Living - Waterfront/Private Pool/Boat Dock/Close to beaches

Sarasota, Florida, United States

Bed

Bath

Sleeps

$191.56

Your Sarasota adventure begins at this marvelous 3-bedroom pool home. With 2 queen beds and 1 king bed, this property offers a wonderful space for guests to relax and unwind. The house is equipped with all the essentials you need. Whether you're exploring the city, enjoying the beach or barbecuing around your private pool, this enjoyable house is the perfect home away from home. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out.

Charming 3-bedroom pool home in serene Sarasota with AC, WiFi

Sarasota, Florida, United States

Bed

2

Bath

Sleeps

$235.68

Discover this charming 3-bedroom gem in Sarasota! Full 3 bedroom/2 Bath home for your stay completely turnkey for all your needs. Private back with Preserve and pond and amazing wildlife to view. This home is 20 minutes from all of Sarasota and Bradenton and 3 miles from the sarasota airport. Venice is 30-40minutes. Easy access to all our area has to offer while you are on vacation!

Sarasota Charm

Sarasota, Florida, United States

Bed

2

Bath

Sleeps

$467.33

Your dream tropical spot. Escape to paradise in this sun-kissed Florida house, just minutes from the pristine white sands and turquoise waters. Enjoy a private heated saltwater pool, tropical landscaping, and a modern home with a fantastic pool deck with outdoor TV, all while being close to vibrant beachside dining and entertainment.

Minutes from Siesta Key, Heated saltwater pool with fabulous pool deck.

Sarasota, Florida, United States

Bed

Bath

Sleeps

$202.57

Mixing resort amenities with homey surroundings, this vacation rental offers the best of both worlds. Stay at this 1-bedroom, 1-bath Sarasota home and enjoy access to a hot tub, 3 pools, putting greens, a fitness center, and more. Those with little ones will enjoy easy access to the nearby playground and splash pad. With fun places like the Sarasota Jungle Gardens and a handful of beaches just a quick drive away, this Florida haven offers endless activities for the whole family!brbr-- THE PROPERTY --brbrWood-Burning Fire Pit | Cable TVsbrbrWith at-home conveniences and sought-after amenities at your fingertips, this well-appointed home is perfect for families looking to explore Sarasota! brbrBedroom: Queen Bed | Living Room: Queen Sleeper Sofa | Screened-In Porch: Queen Sleeper SofabrbrRESORT AMENITIES: Hot tub, 2 outdoor pools, indoor pool, splash pad, putting greens, cornhole, volleyball court, basketball court, tennis courts, shuffleboard courts, game room, fitness center, playground, restaurant, cafeteria, coin laundry, golf cartbrOUTDOOR LIVING: Screened-in porch, yardbrKITCHEN: Well-equipped, cooking basics, dishware & flatware, microwave, toaster, drip coffee maker, trash bags, paper towelsbrINDOOR LIVING: Dining area, laptop friendly, ceiling fansbrGENERAL: Free WiFi, in-unit washer & dryer, laundry detergent, iron & board, towels & linens, complimentary toiletries, hair dryer, central A/C & heating, electric heatingbrFAQ: 3 stairs required to access, pet fee (paid pre-trip)brPARKING: Driveway (2 vehicles), free street parkingbrbr-- THE LOCATION --brbrFUN IN THE SUN: Indian Beach (9.4 miles), Lido Key Beach (10.5 miles), Siesta Key Beach (13.4 miles), Turtle Beach (14.6 miles), Venice Beach (19.7 miles), South Jetty Beach (20.8 miles), Cortez Beach (22.8 miles)brSARASOTA ATTRACTIONS: Big Cat Habitat Gulf Coast Sanctuary (1.8 miles), Downtown Sarasota (6.1 miles), Sarasota Jungle Gardens (9.6 miles), The John and Mable Ringling Museum of Art (10.6 miles), Tibbals Learning Center at The Ringling (10.9 miles), Ca' d'Zan (11.1 miles), Mote Marine Laboratory & Aquarium (11.3 miles), The Bishop Museum of Science and Nature (18.0 miles)brTHE GREAT OUTDOORS: Celery Fields (2.1 miles), Bayfront Park (3.0 miles), Marie Selby Botanical Gardens Downtown Sarasota Campus (7.6 miles), Myakka River State Park (13.2 miles), Riverwalk (17.9 miles)brHIT THE LINKS: Tatum Ridge Golf Links (1.6 miles), The Founders Golf Club (3.0 miles), The Groves Golf Course (5.4 miles), Legacy Golf Club at Lakewood Ranch (6.1 miles), Serenoa Golf Club (8.9 miles), Lakewood National Golf Club (13.0 miles)brDAY TRIPS: Tampa (56.5 miles), Clearwater (60.9 miles), Busch Gardens Tampa Bay (61.8 miles), Walt Disney World Resort (108 miles), Universal Studios (119 miles), Orlando (127 miles)brAIRPORT: Sarasota-Bradenton International Airport (10.7 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Pet friendly w/ $70 fee (+ fees & taxes, dogs only, max 2)br- No events, parties, or large gatherings br- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires 3 stairs to access and may be difficult for guests with limited mobility

Bright Home: Pool Access & Screened-In Porch!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$2494.15

Summary:brbrVunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result Unmatched value for travelers who expect more from their getaway.brbrbrbrThe Space:brbrWelcome to The Overlook, a refined coastal retreat that blends thoughtful design, luxury amenities, and indoor-outdoor living in one of Siesta Key’s most coveted locations. With over 5,000 square feet of interior and exterior living space this modern estate offers Gulf-facing balconies, a rooftop terrace with fire pit, a resort-style pool, waterslide, poolside basketball hoop, oversized spa, Putt-Putt Golf, Ping Pong, Ring Toss, billiards, Nintendo Switch gaming console, expansive outdoor entertaining areas, and spacious bedrooms. So, whether you’re relaxing poolside, entertaining on the rooftop deck, or hosting friends and family, planning a day trip or getting out on the town, this estate promises a vacation experience like no other.brbrbrbrFloor Plan Description (by level):brbrbrbrGround Level:brbrGuests are greeted with a private entry foyer with staircase and elevator access to all levels above, including the rooftop deck. There are also 2 garages for covered parking (EV charger equipped) in addition to driveway parking provided. The home’s beach gear is also stored here, including bikes, beach wagons and chairs, alongside a convenient fridge and freezer combination. brbrbrbrOutdoors, you’ll find a private resort-style pool with a sun shelf and ample chaise loungers for in-water and pool side seating. Just steps away, a Putt-Putt green, ping pong table, and ring toss provide active entertainment options. The covered pool patio offers an extensive array of seating featuring soft seating accommodating up to 14 people, a dining area that accommodates 14, and bar seating for up to 6. The outdoor kitchen includes a grill, beverage fridge with ice maker, and ample countertop space storage with drawers and cabinets. 3 TVs are placed throughout the covered pool patio for seamless viewing from all angles. brbrbrbrThe First Level of Living (2nd Floor):brbrThis level includes two private King bedrooms, Master bedroom 1 and bedroom 2. Master Bedroom 1, which features a king bed, walk-in closet, en suite bath with double sink vanity, a freestanding tub in shower, and access to its own private balcony with soft seating for two. Bedroom 2 features a king-size bed, walk-in closet, en suite bath with single sink vanity and walk-in shower. brbrbrbrAt the heart of this level is the homes great room. The gourmet kitchen is fully equipped with a 48-inch range, double wall ovens, microwave drawer, dual dishwashers, toaster, coffee maker, and more. The kitchen is very well appointed with cookware, bakeware, dishware, cutlery, and specialty items like crockpots, blenders, and more. The kitchen is set up perfectly for you to host your family or to support private in-home catering services that our team can help you arrange through one of our preferred vendors for an additional cost. If you have any questions about these kitchens or their supplies, our reservationists would be happy to provide more details. A nearby pantry includes an additional full-sized refrigerator with ice maker, sink, trash pull-out, and utility cabinet. The living room offers an oversized custom modular sofa that comfortably seats 10, and an 80”+ TV. The adjacent dining space includes a table with seating for 8, and a large center island with bar seating for 6 and a nearby bar top with 4 more stools. Two balconies expand this space outdoors: a rear balcony which is furnished with a dining table for 14, and soft seating for 2 and a front balcony with additional soft seating for 2. A convenient half bath completes this level. brbrbrbrThe Second Level of Living (3rd Floor):brbrThis level was designed for both restful retreats and social fun. The Club Room includes a billiards table, built-in bar with beverage fridge and ice maker, lounge seating for 6, a built-in desk for remote work or reading, and soft seating on two balconies — including a swing style daybed, club chairs for shade lounging with peaking gulf views. A laundry area with two stacked washers and dryers, folding space, rod, and utility sink adds practicality for large groups.brbrbrbrThis level also houses four bedrooms, including the home’s Bunk Room. Bedrooms 3, 4, and 5 offer a king bed, en suite bath with a walk-in shower and vanity. Bedrooms 4 and 5 have private or shared balcony access with soft seating and sweeping views. Bedroom 6 is the Bunk Room and features a twin-over-twin bunk and a queen-over-queen bunk, plus an open closet system, a single sink vanity, and a bathtub/shower combo.brbrbrbrThe Third Level of Living & Rooftop Deck (4th Floor):brbrThe Overlook has a stunning rooftop deck, designed to elevate your vacation experience. This stylish space includes a covered lounge area with bar seating for 7, soft seating for 4, and a fire pit table surrounded by plush chairs. A built-in bar area below the outdoor TV includes a beverage fridge with ice maker, trash storage, and cabinetry. Railing-style umbrellas provide shade, while thoughtful design ensures everyone has a seat with a view. Whether sipping sunset cocktails, enjoying a game of cornhole, or watching the game under the stars, this rooftop retreat is the ultimate place to gather and unwind.brbrbrbrGetting Around:brbrThis home is located just a short walk from the powdery sands of Siesta Key Beach and the vibrant Siesta Key Village. The Overlook offers both full and peaking Gulf views from most rooms and common spaces located on the 2nd living level as well as the rooftop terrace. The home is conveniently located to everything on Siesta Key. And, if you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft to the mainland Sarasota area (5 minutes) and downtown Sarasota (20-25 min) for access to the Sarasota’s Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, grocers, and more. And, day trips to Lido Key, Anna Maria Island, Venice Beach, Myakka State Park and so much more are all less than an hour away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away! So, whether you’re relaxing poolside, entertaining on the rooftop deck, or hosting friends and family, planning a day trip or getting out on the town, this estate promises a vacation experience like no other.brbrbrbrOther Things to Note:brbrThis Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms.brbrbrbrAccessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information.brbrbrbr*Don't forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!brbrbrbrInteraction with Guests:brbrPersonal service and attention to detail define the Vunique Difference. We want your vacation to fit your schedule, which is why we offer flexible bookings starting at just 3 nights for most of the year and any-day arrivals. Our homes are spacious and thoughtfully designed, made for connection as much as comfort. Here, luxury isn’t an upgrade – it’s the standard. Within our portfolio of branded residences, you have every amenity that you need for an unforgettable stay - waterslides, movie rooms, resort-style pools, sport courts, golf simulators, climbing walls, putt-putt courses, zip lines, gaming systems, rooftop decks, biked and beach equipment and more. Our proactive maintenance team ensures everything is in top shape before your arrival, and each property has a dedicated manager who welcomes you personally and stays available throughout your stay should you need anything. Transparency is at the core of everything we do. What you see is what you pay – no hidden fees for pool heat (up to 86 degrees), bikes, propane, or any of the extras that should already be included. Why settle, when you can stay somewhere extraordinary

Gulf Views, Waterslide, Spa & Rooftop Lounge

Sarasota, Florida, United States

Bed