Vacation Rentals By Owner In Sarasota, FL

Beautiful vacation villa located in the popular Village Des Pins complex, only a short drive to Siesta Key Beach, voted multiple times the #1 beach in the USA. This community has a large resort style pool, hot tub, 2 tennis courts, basketball court, and a putting green. There is a serene picnic area with a grill and also a clubhouse with a pool table. brbrMany restaurants and entertainment are in close proximity.brbrThere is all new furniture and décor in this villa. The master bedroom has a king bed, second bedroom has a queen bed. We have a single roll away bed and air mattress for extra sleeping. There is also a small chair that makes a sleeper for a young child also. Plenty of room for the entire family!brbrThere is a large television in the living room and a second TV in the master bedroom. We have given you all the comforts of home, including essentials such as shampoo, body wash, and other extras so you can pack light. There is a washer and dryer with all your detergent needs. We have beach chairs, putters and golf balls to use on the putting green, a cooler to take your food and drinks to the beach, and more!brbrThe front and back screened in porch and lanai make this unit special. You will love the privacy of the back lanai while sipping your morning coffee. brbrOwners are minutes away and always available to answer any questions.

Village Des Pins 2/2 Condo close to Siesta Key Beach!!

Sarasota, Florida, United States

Bed

Bath

6

Sleeps

$351.92

Experience in Sarasota’s coveted coastal district — 3 blocks to the bay and ½ mile to Siesta Key’s sugar white sand!brbrEffortless access to Siesta & Lido Beaches, Sarasota’s dining & arts scene, St Armand’s boutiques, & Gulf Coast adventure!brbrYour Mediterranean-style 2BR bungalow sleeps 6 (“west of trail”), pairing resort comfort & coastal design—chef grade kitchen, beach gear, Smart TVs, laundry, fast WiFi, & a workspace. Perfect for slow mornings and relaxed evenings. brbrOutdoors savor al fresco dining in your , stroll the serene palm-lined neighborhood, the day’s catch, & - !brbrWalk/bike to neighborhood cafés, markets, parks, and the water!brbr Weekly Stays, Sat–Sat yearlongbr Dec–Feb weekly and monthlybrbr~~~~~~brbr brbrA serene sanctuary of - - — where custom furnishings, natural textures, and curated finishes create a stay that feels more like a lifestyle than a getaway.brbr▫️ with yoga & meditation br▫️ & under the palmsbr▫️ Dine indoors, garden-side, or picnic on the beachbr▫️ a with & premium cookwarebr▫️ Luxe linens & pillow menu, artisanal bath amenities, and coastal-inspired art throughoutbr▫️ — chairs, umbrella & cooler for carefree Gulf daysbr▫️ 65” Smart TV with YouTube TV, Max & Hulu + Smart TVs in every bedroombr▫️ - - for streaming, remote work & playbr▫️ — perfect for yoga or quiet morningsbr▫️ for exploring neighborhood cafés & coastlines (they deliver!)br▫️ Bose speaker, Victrola & house guitar for the perfect vacation soundtrackbr▫️ & - for slow, sunny afternoonsbr▫️ - touches — toys, games & kid-friendly dinnerwarebr▫️ ’ + (available with advance request)br▫️ & , thoughtful starter essentialsbr▫️ Secure, - & private br▫️ Concierge recommendations for local charters, spas & diningbr▫️ brbrLobster on the grill, beach picnics, footprints in the sand — vacations the way they’re meant to be. brbr~~~~~~brbr brbrWellness-retreat vibes— plush beds, luxe linens, blackout curtains, sleep sounds machines, Smart TVs.brbr : 1 King · 1 Queen · 1 Queen Sleeper Sofa · 1 Twin Daybedbrbr — oversized windows, lush garden views, Saatva mattress, black out curtains, smart TV, sleep sounds machine, individual reading lights, tallboy dresserbrbr — serene rainforest mural, tropical outlook, black out curtains, closet storage system, smart TV, sleep sounds machine, individual reading lightsbrbr (Living Room)brbr — marble bathroom, walk-in shower, artisanal bath amenities, oodles of fluffy towels brbr~~~~~brbr / brbrSituated on an upscale palm-lined street, FlipFlopsOn III puts you minutes from sugar white beaches, the Bay, downtown Sarasota, St Armands Circle, and the best of Florida’s Gulf Coast!brbr▫️Siesta Key – America’s #1 beach, with powder-soft sand, turquoise water, and a fun après-beach scene in Siesta Village.brbr▫️Lido Beach & St. Armands Circle – Serene sands and wildlife meet chic dining and upscale boutiques in this stylish, walkable hub.brbr▫️Historic Sarasota – Waterfront charm, art galleries, boutiques, oodles of little cafés, and yacht watching—all with a vibrant local vibebrbr▫️Local Marinas – You’re surrounded by Sarasota’s best — from Marina Jack for sunset cruises and waterfront dining to nearby launches for pontoons, kayaks, jet skis, or fishing charters.brbr~~~~~~brbr brbrLive life like a Gulf Coast local —minutes from tranquil shores & endless adventure! Do everything, or nothing at all!brbr▫️Lounge on white-sand beaches or bike to a br▫️Spot , kayak the mangroves, or through Midnight Passbr•▫️ to cast a line (3 blocks) or book a - br▫️Visit , , , , br▫️Indulge in a at The - . br▫️Tee off at , , , or try all ~12 of Sarasota’s public coursesbr▫️Pompano Park’s are always a treat!br▫️Browse art galleries, farmers markets, upscale boutiques, & live local musicbrbrWOW! What a life!brbr~~~~~brbr brbrEverything you need, just minutes away:brbr- Coffee, organic bakery, & café – 1 blockbr- Connor’s Steakhouse – 3 blocksbr- Roberts Bay kayaking & fishing – 3 blocksbr- Gourmet Market & Grocery store – 3 blocksbr- Playground – 4 blocksbr- Gym, Pilates, LA Fitness – 5 min drivebr- Siesta Village dining/nightlife – 5 min drivebr- Walt’s Fish Market – 1 milebr- Southside Village dining/boutiques – 1 milebr- Downtown Sarasota boutiques – 3 milesbr- Marina Jack Yacht Basin - 3 miles br- St. Armands Circle – 5 miles brbr~~~~~~brbr brSpring–Fall ( – ) — Weekly getaways, - - — perfect for families, friends & beach lovers!brbr• Monthly Escapes ( – ) — Offered as relaxing, full-month retreats for our snowbirds & extended-stay guests.brbr , just reach out — just message us here on VRBO — we’ll always find you some great dates!brbr~~~~~~brbr brbrYour stay is in trusted hands. We love this place and we want YOU to love it too. brbr• FlipFlopsOn homes have been + for their guest experiencebr• Hosts have 250+ 5-star reviews!brbr~~~~~~brbr brbrBy completing your booking and payment, Guest agrees to the terms of the rental agreement uploaded under VRBO’s ‘Rules & policies’. brbr~~~~~~brbr & brbrFor your peace of mind, FlipFlopsOn III is equipped with two outdoor security cameras — one at the front porch and one near the main entrance on the back patio, where the self-entry keypad is located. They face outward only, are motion-activated, and may record video and audio to help safeguard guests and packages.brbrNo cameras are located inside the home, and there is no interior recording of any kind.brbrNote: Guests enter through the back-patio main entrance — the home’s original front doors have been carefully preserved as part of its restored architectural design.

FlipFlopsOn III • 1/2 Mile to Siesta Key • FL’s Gulf Coast • Sarasota

Sarasota, Florida, United States

Bed

1

Bath

6

Sleeps

$326.14

Tastefully decorated charming home on a quite cul de sac with beautiful gardens, located a block away from a mesmerizing Red Bug Slough preserve, 3.5 miles away from a renowned Siesta Key Beach, and 0.3 miles from the Legacy Trail. Two bedrooms with queen beds and one office room. The Master bedroom overlooks garden with sliding doors. Newly renovated a walk-in shower in the Master Bathroom and a tub/shower in the Guest bathroom. The open concept kitchen is complete with stainless steel appliances and beautiful marble/wood counter tops. Full size stackable laundry appliances in the laundry room. Parking in driveway. The rate includes grounds maintenance, internet and an Electric cap provided by the owner. House Rule: No smoking. No pets. No TV zone. No burning candles inside of lodging. No parties. **Taxes and fees not included.

Home to flourish

Sarasota, Florida, United States

3

Bed

Bath

4

Sleeps

$242.15

This 3 bedroom 2 bath, Bonus Room 1806 square foot home in Gulf Gate is oozing with Southern charm! Will sleep 6. Beautifully remodeled split plan is spacious, open and bright. The updates include a sleek, modern kitchen, upscale bathrooms with gorgeous lighting, beautiful new plank flooring, and beachy coastal colors for the interior and casual Florida furnishings through out the home. The home has everything you need for a perfect stay, including the necessities for days spent at the beach! The backyard is huge, private and you could call it a sanctuary. Perfect backdrop for wonderful gatherings, grilling, or just relaxing and enjoying gorgeous days and balmy nights – Southern style. Gulf Gate Village offers a charming mix of pubs, shopping, exquisite dining, casual dining and entertainment. Only seven minutes away is the world famous Siesta Key, home of the whitest sand in the world. Siesta Key is also home to some of the most gorgeous views on Earth! Miles and miles of beaches, shopping, dining, boutiques, beach bars, music etc. So much to do and see here! Downtown Sarasota is a short 15-minute drive where you will find arts and entertainment, shopping, dining, antiques, boutiques and so much more. Across John Ringling Bridge you’ll find St Armand's Key, which is absolutely worth a visit. Again, the best of the best in dining, shopping, boutiques and gift shops.

Gulf Gate Private Escape

Sarasota, Florida, United States

Bed

Bath

Sleeps

$227.62

Beautiful one bed one and a half bath condo on 5th floor with pool view and in unit laundry with all appliances. Centrally located close to SRQ airport, UTC mall, SMH hospital, walking distance to downtown, arts, museums and of course the beaches with kayak to launch by the bayou. The building comes with Electric charging stations, community pool, SPA, fitness center with internet, Kayak/paddle board,beach chairs,fire pit and parking. This unit does not come with a Boat Slip. Background check required by HOA

Charming 1-bedroom condo by the water

Sarasota, Florida, United States

Bed

Bath

Sleeps

$304.12

Summary:brDiscover the enchanting Siesta Key experience by staying in this stylish 2BR 2Bath condo whose relaxing design enhances your vacation. The search for a perfect getaway with an abundance of amenities, all conveniently located near fantastic dining, entertainment, beautiful beaches, and more, ends here.brbr✔ 2 Comfortable Bedrooms + Sofa Bedbr✔ Open Design Livingbr✔ Fully Equipped Kitchenbr✔ Balconybr✔ TVsbr✔ High-Speed Wi-Fibr✔ Community Amenities (Swimming Pool, Sports, BBQ, Parking)brbrLearn more below!brbrThe Space:brImmerse yourself in the relaxing, light-filled ambiance that flawlessly complements the modern design of this inviting condo. From room to room, you'll discover an array of contemporary amenities thoughtfully placed to enhance your stay.brbrThe open-concept living area is the heart of this retreat, creating the perfect setting for fun gatherings. The ample space and well-designed design guarantee that every moment spent here is enjoyable and memorable.brbrAs day turns to night and you seek a tranquil rest, you'll find it in two snug bedrooms that promise comfort and style, ensuring you wake up refreshed and ready to embark on your next thrilling Siesta Key adventure.brbrBut one of the most treasured features of this condo is the charming balcony. Step outside and savor the fresh air and lovely views of the pool area; this balcony is the ideal spot to unwind with a morning coffee, bask in the sun, or savor a glass of wine while the sun sets, casting a warm, golden glow over the mesmerizing vistas. brbr★ LIVING ROOMS ★brThe moment you enter the condo, you'll be drawn by the comforts of the living room, setting the scene for countless memorable evenings.brbr✔ Comfortable Sofa with Pillows (can be extended into an extra Queen-Size Bed)br✔ Smart TVbr✔ Cozy Sofa Chairs with Throw Blanketsbr✔ Coffee Tables and Reading Lampsbr✔ Access to the Balconybrbr★ KITCHEN & DINING ★brStock up on fresh ingredients, arrange them on the expansive countertops and the generous kitchen island, and use our culinary tools to craft delicious dishes for the entire party.brbr✔ Microwavebr✔ Stovebr✔ Ovenbr✔ Coffee Makerbr✔ Hot Water Kettlebr✔ Refrigerator/Freezerbr✔ Dishwasherbr✔ Sink - Hot & Cold Waterbr✔ Traysbr✔ Glassesbr✔ Silverwarebr✔ Pots & PansbrbrWhat are you waiting for Set the table and serve those delicious meals for a tasty homemade feast for the entire family.brbr✔ Dining Table with Seating for 4br✔ Kitchen Bar with Seating for 3brbr★ SLEEPING ARRANGEMENTS – 2 BEDROOMS ★brMove around the condo to discover two inviting bedrooms, each thoughtfully adorned to provide the ultimate relaxation following a thrilling day at Siesta Beach.brbr♛ Master Bedroom: King-Size Bedbr♛ Bedroom 2: Two Twin Beds (can be set up as one King-Size Bed)brbrEvery bedroom comes furnished with a matching array of conveniences.brbr✔ Ensuite Bathrooms br✔ Premium Pillows, Linens, and Sheetsbr✔ Flat-Screen TVsbr✔ Closets with Hangers and Shelvesbr✔ Dressers with Spacious Drawersbr✔ Safety Deposit Boxbr✔ Night Stands with Reading Lampsbrbr★ BATHROOMS ★brBoth bedrooms boast relaxing ensuite bathrooms stocked with clean towels and essential toiletries for maximum comfort and convenience.brbr✔ Walk-In Showerbr✔ Vanity (Double in the Master Bath)br✔ Mirrorbr✔ Toiletbr✔ Towelsbr✔ Hair Dryerbr✔ Essential Toiletriesbrbr★ BALCONY ★brEmerge onto the balcony from the living space and be captivated by the splendid vistas of the inviting swimming pool area. It's an ideal spot for a refreshing drink during a slow afternoon.brbr✔ Cozy Seating AreabrbrYour unforgettable Siesta Key retreat awaits – book your stay with us today and make cherished memories in this luxurious oasis.brbrGuest Access:brThe condo is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home.brbrOther than the already mentioned amenities, the home also features:brbr✔ High-Speed Wi-Fibr✔ Air Conditioningbr✔ Beach Accessories (Chairs, Cooler, Toys, Parasols)br✔ Laundry Closet (Washer/Dryer, Iron/Board, Detergent, Dryer Sheets)brbrThis condo is located within the esteemed Bay Oaks Condos, just a short distance from Siesta Key's South-end Village, with shopping, restaurants, and bars. It offers a wide range of exceptional amenities at your disposal during your visit.brbr✔ Swimming Pools with Sun Loungebr✔ Waterfront Picnic Area with Charcoal BBQ Grillsbr✔ Tennis Courtbr✔ Free ParkingbrbrThe Neighborhood:brThe condo is a part of the high-end Bay Oaks Condominium, just a few minutes away from the vibrant Siesta Village in Siesta Key, a tropical haven on the west coast of Florida that embodies the essence of paradise. brbrIt is known for its powdery white sands, crystal-clear waters, laid-back atmosphere, and some of the most breathtaking beaches in the United States. Siesta Beach, in particular, has earned acclaim for its powdery, quartz-crystal sands, which stay cool even on the warmest days. Sunset at Siesta Beach is a spectacle not to be missed, with hues of orange and pink painting the sky as the sun dips below the horizon.brbrBeyond the beaches, Siesta Key offers a wide range of outdoor activities. Kayak through the calm waters of the mangrove tunnels at South Lido County Park, paddleboarding in the Gulf of Mexico, or embark on a fishing charter to catch your dinner. Nature enthusiasts will appreciate the lush landscapes and wildlife in the nearby Myakka River State Park.brbrSiesta Key Village is the heart of the island's dining, shopping, and entertainment scene. Stroll along quaint streets with boutiques, surf shops, and art galleries. Savor fresh seafood at beachfront restaurants, sip tropical cocktails at vibrant bars, and enjoy live music under the stars.brbrThe warm waters surrounding Siesta Key beckon adventure seekers to explore. Try windsurfing, jet skiing, or parasailing for an adrenaline rush. Scuba diving and snorkeling enthusiasts will be delighted by the vibrant underwater world of the Gulf. For a more leisurely experience, rent a boat, explore the Intracoastal Waterway, or take a dolphin-watching tour.brbrCome and discover the beauty and tranquility of this coastal gem, where every day feels like a beach day in paradise.brbrHere are some places of interest you'll be looking to visit during your stay.brbr✔ Siesta Key Beach 5mins (10 min walk away)br✔ Crescent Beach (8 min away)br✔ PARASAIL SIESTA (3 min away)br✔ Siesta Key Watersports (5 min away)br✔ Siesta Key Village (8 min away)br✔ Marie Selby Botanical Gardens (15 min away)br✔ Sarasota Jungle Gardens (25 min away)br✔ Lido Key Beach (25 min away)br✔ South Lido County Park (25 min away)br✔ Mote Marine Laboratory & Aquarium (28 min away)br✔ St. Petersburg (55 min away)br✔ Tampa (1h 5 min away)br✔ Fort Myers (1h 20 min away)brbr***Distance times are calculated if traveling by car.brbrGetting Around:brIf you arrive by car, you will be happy to know that we offer free parking. However, if you would like to avoid driving during your stay, there are many convenient, easily accessible transportation options close to our home.brbr✔ Siesta Key Breeze Trolley (free)br✔ Taxibr✔ Lyft & UberbrbrIf you are flying in/out of the area, the best way would be at the below airport:brbr✔ Sarasota Bradenton International Airport (25 min away)brbrOther Things to Note:br★ RENTAL AGE REQUIREMENT ★brRENTERS MUST BE 25+, ANYONE FOUND RENTING TO BE UNDER THE AGE OF 25 YOUR STAY WILL BE CANCELLED AND NO REFUND WILL BE ISSUEDbrbr★ ADDITIONAL ACCOMMODATION ★brTraveling in a larger group, or your preferred dates are already taken You'll be happy that we offer additional accommodation in the area. Feel free to browse our host profile for a complete list of fantastic stays, and contact us with any questions.brbr★ CLEANING & SANITIZATION ★brHealth, safety, and well-being of our guests are of utmost importance. For this reason, we use a thorough cleaning process after each check-out.brbr★ NO PETS ALLOWED ★brWe love those little (and not so little) furry bundles of joy. Sadly, our home is not suitable for accommodating them.brbr★ NO SMOKING INSIDE ★brPlease refrain from smoking inside the home! Any smoking evidence will result in a fee for odor removal and furniture cleaning.brbr★ NO PARTIES/EVENTS ★brWe kindly ask you to treat our home as your own to preserve its pristine condition for future guests and your return visits.brbrThank you very much. We look forward to hosting you!brbrInteraction with Guests:brWe will be accessible to guests via phone, text, or the Booking app. brExpect a quick and prompt response. We give our guests space but are available for every inquiry.brbrContact us now so we can begin arranging your perfect vacation!

Siesta Key Paradise - Close to Beach & Village

Sarasota, Florida, United States

Bed

Bath

Sleeps

$129.95

You & your companion will enjoy private entrance to the guest house, easy access to everywhere.brFamily & friendly neighborhoods, very peaceful, free parking, walking distance to Aldi & Publix, minutes to nation #1 Siesta Key Beach, 24hrs laundry mat, SMH & downtown, surrounded with many international 5-star restaurants, very quiet but near main road like US41 & straight east to highway 75.brThe spacebrmaster suite just 5 minutes away from Siesta Key beach. lived like a heart in the central of Sarasota. our place will leave you a heart of paradise exited on earthbrGuest accessbrprivate access with plenty of Sarasota nature yardbrOther things to notebrplease let us know if you need any assistance or information about attractions.

Entire Guesthouse 5 mins to Siesta key & downtown.

Sarasota, Florida, United States

Bed

Bath

Sleeps

$143.14

Our place provides accommodations with free wifi, 11 miles from The John and Marble Ringling Museum of Art, 7 miles from Sarasota Opera and 7 miles from Marina Jack Restaurant and Marina. the property has garden and free private parking.brThe spacebrThe air-conditioned vacation home consists of one separate bedroom, one bathroom with a hairdryer, a seating area area, and a livingroom. there's a dinning area and a kitchen complete with microwave, a fridge and an ovenbrGuest accessbrSeparate and private entrance to the premises to private carport with a table and chairs for enjoying the weather or fresh air.brOther things to notebr➡️ Please only use the combinations to enter or exit the house.br Do not lock yourself outside with the door knobslocks

Entire Home mins Siesta Key/closed to downtown

Sarasota, Florida, United States

Bed

Bath

Sleeps

$191.92

A coastal retreat in a tranquil country setting just minutes from UTC’s dining, shopping, and Nathan Benderson Park. I-75 is under 3 miles away, with Siesta Key and Lido Beach within 40 minutes. Enjoy a full kitchen, 2 king bedrooms, a spacious bath with double vanity, high-speed Starlink internet, a fire pit, and beach gear. Unwind on the private patio, and bring your pet—this getaway is pet-friendly!brbrWhat You'll Love:brbr-Amazing location only 5 MINUTES from the University Town Center (UTC) mall, Nathan Benderson Park, new Mote Marine location, and I-75 on rampbr-Peaceful, light and airy coastal ambiance all throughout the housebr-Recently updated space with new furniture and almost all new appliancesbr-Fully-equipped kitchen complete with dishwasher, oven/stove, microwave, and new fridge with freezer; pots and pans and Keurig K-Duo coffee makerbr-Hidden tranquil and secluded location off of a private drive and at the backend of a 1-acre propertybr-900 square feet of living spacebr-65 smart TV with host access to Netflix, Hulu, & YouTube TVbr-2 bedrooms equipped with king-sized beds complete with charging stationsbr-Brand new Helix mattresses for each bedbr-Walk-in shower with large double vanity in the bathroombr-Washer/dryer for easy laundering throughout your staybr-Private patio/balcony space to enjoy the space peacefully and privatelybr-Private outdoor space with 6 chairs around a large, custom-made fire pit, perfect for enjoying s'mores with friends and family in the evening.br-Lightning fast Starlink internet accessbr-Private on-site parking: comfortably parks 2 full-sized vehicles right next to the entryway stairsbr-Pet-friendly: plenty of open space for dogs to run, pet blankets provided for furniture protection and pet bowls provided as wellbr-Beach gear provided! 4 beach chairs, 6 beach towels, umbrella and cooler bag to make beach-going a little more convenientbrbrTraveling with little ones We've partnered with BabyQuip so you can easily rent cribs, strollers, and much more, delivered right to your door! Just follow this link to discover all the equipment available for you to rent to make your vacation as relaxing and seamless as possible: https://www.babyquip.com a=d8be8fe. brbrThe Space:brbrAfter a recent comprehensive revamp of the guesthouse, we are excited to present Coastal Hideaway. Every inch of this space was thoughtfully and lovingly updated to demonstrate the unique experience of enjoying a private, almost country outdoor setting while simultaneously enjoying an indoor coastal setting that speaks to what Sarasota is most famous for: her beaches.brbrThis amazing 2/1 guest house rests at the backend of our 1-acre property. While my husband and I live in the main house at the front of our property, guests will have private and exclusive access to the guest house on the second floor of our ADU (accessory dwelling unit). The first floor of the ADU is a garage and is used to park 1 of our vehicles; the garage door may be heard in the guest house occasionally from the space as it is opened and closed.brbrThe keyless entry lock allows for self-check in and opens to a very open floor plan where the full kitchen and the ample living area is immediately displayed. Each bedroom is spacious and includes king-sized beds, brand new Helix mattresses, a full length mirror, a 5-drawer dresser, and open-concept closets with rods (not shown in pictures) to hang clothing. The bathroom hosts a new walk-in shower and 80 inch double sink vanity.brbrThe space is 900 square feet and comfortably sleeps 4 adults; however, the couch is modular and could be arranged to would allow for 1-2 more adults or children for additional sleeping.brbrAll water provided in the space is from our well and the central heating and cooling is controlled via thermostat in the guesthouse for guests to control for their own liking throughout their stay.brbrThe TV is an Amazon Fire TV and includes subscriptions to Youtube TV (for local channels), Netflix, Hulu, and Amazon Prime. WiFi is high speed at ____mbps. Additionally, we do not use cameras or any monitoring devices of any kind so our guests have complete privacy throughout their stay.brbrBeach amenities include: 4 beach chairs, 6 beach towels, a beach umbrella and a cooler bag.brbrThe guest house is within a 5 minute drive to the UTC Mall/surrounding area, Nathan Benderson Park, the future home of the new Mote Marine location, and I-75. Siesta Key Beach is approximately a 40 minute drive away and Lido Key Beach is approximately a 30 minute drive away (depending on traffic and time of day).brbrThis space is on the second (top) floor of the back building on our 1-acre property. Parking is provided on the shelled area right by the stairs and the space is accessed by ascending the stairs to the entrance. The entry door is equipped with a keypad for convenient self-check in for guests upon arrival. Entry code for the keypad will be provided to you prior to check-in.brbrThe first floor of the building is a garage and used by us to park 1 vehicle and is not available for guest use. The sound of the garage door opening and closing can be heard from the guesthouse; however, guests maintain private and exclusive access to the guesthouse on the second floor.brbrWe also have a friendly boxer who lives with us at the main house. She will be kept separate from the guesthouse and that surrounding area, but guests may see her out and about at our main house.brbr*If you bring pets, please keep them inside with you overnight and do not allow them to run loose/unsupervised due to potential wildlife*brbrOur neighbors have chickens and a rooster can be heard distantly crowing throughout the day; this just adds to the country charm of the space :)

Apartment

Coastal Hideaway: 2/1 guest house close to UTC!

Sarasota, Florida, United States

Bed

1

Bath

4

Sleeps

$105.28

This is a newly renovated condominium featuring an open floor plan, all floors are vinyl plank. The kitchen has new appliances and quartz counter tops and counter chairs to seat three. This all opens to dining and the family area with open views of the landscaping. There is a lanai with tables and chairs to relax from your day at the pool or beach.brbrThe unit has two large bedrooms that sleep two, each with bathrooms for both. The master bedroom has plenty of light, a king-size bed and 55-inch LG TV. The master bath has a walk-in shower, a vanity with two sinks and a large walk-in closet brbrThe guest room has a queen size bed, and a 55-inch LD TV mounted on the wall. The second bathroom is located next to the guest room and has a single sink and a tub/shower.brbrThe washer and dryer are in a separate laundry room located across from the kitchen.brbrOut of the Lanai and a short walk is the pool with plenty of room to relax and a Gazebo for cooking and entertainment.

This is a newly renovated two bed / two bath condominium.

Sarasota, Florida, United States

Bed

Bath

Sleeps

$128.8

This 1/1 unit is newly renovated with full kitchen, privately fenced patio and yard and private laundry. The unit has one sound proofed shared wall.brbrWalk to Arlington Park pool, basketball and tennis courts, workout facility and playground. Also walkable to SMH and Southside Village restaurants & shops. Minutes from Bayfront Park, Selby Botanical Gardens, Marina Jack, St Armand's/Lido Key and Siesta Key.brbrGreat neighborhood to walk. Property has large trees and lots of birds. This area of Sarasota allows for weekly stays, per City ordinance. VR24-00263

Mid-Century 1/1 Near Downtown/Siesta Key/SMH/Arlington Park

Sarasota, Florida, United States

Bed

Bath

Sleeps

$251.83

Spacious, nicely furnished 3 bdrm, 2 bath home with private heated pool. Located very close to Siesta Key beaches, restaurants and shopping. Features split floor plan, large living room with office desk in corner, master bdrm with king size bed, 2. bdrm with queen size bed and 3. bdrm with Trundle bed (1 full size bed and 1 twin bed underneath the full). Laundry room inside the house, 2 car garage; large, screened outdoor space and fence for privacy. Sleeps 6 maximum, incl. children.

Private Pool home/close to Siesta Key beaches

Sarasota, Florida, United States

Bed

Bath

Sleeps

$208.61

Pinkie Flamingo Welcomes You To The Catch of The Day at Harbor Towers!brQueen / Queen / Twin Bunks / Sleeper SofabrbrAlways an excellent choice in any of the wonderful, local seafood restaurants around the Siesta Key area, The Catch of the Day is fresh and fabulous. And at Harbor Towers…it is the one you want for your next vacation rental. Located in the desirable waterfront community in the heart of beautiful Siesta Key, this 2-bedroom ground floor condo is ready and waiting to serve up a vacation experience you will treasure forever. Recently added to her collection of outstanding guest nests, Pinkie Flamingo is proud to offer this little slice of paradise.brbrGuests at The Catch of The Day enjoy full resort access to all that Harbor Towers offers. Relax by either of the two “always swimmable” community pools with year-round water temps of 85 degrees. Socialize at the Grilling Patio while preparing your favorite family feast on any of 4 propane grills… then dine al fresco under the covered patio. Pinkie's sporty friends may also access the well-equipped fitness center or the three tennis courts on site. The marina setting offers unparalleled views of more than 40 feet of waterfront and memorable photo opps are yours to be had at the charming gazebo.brbrLet's Go To The Beach!brbrConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Siesta Key achieves its lofty position in the beach rankings among some fierce competition. This 8-mile barrier island delivers on every level imaginable! Public beach access points are frequent including the large Siesta Key Park, with dining, restroom facilities, lifeguards and lots of parking. “This is as world-class as it gets!” says Pinkie, who can often be spotted soaking up the sun on a sunny afternoon. A total beach snob of sorts, Pinkie is quick to highlight the exceptionally fine snow-white crunchy sand and wide walkable beaches. With a shallow shelf that extends far out in the Gulf, the turquoise sparkling water is almost always the right temperature for a dip. A free trolley carries patrons up and down the island…often with the ultimate destination of Siesta Key Village. The heart and soul of the island, “The Village” is the hub of activity with beach bars, restaurants and touristy shops. brbrWhat Pinkie Loves About Catch of The Day at Harbor TowersbrOver 1400 sq ft of living spacebrDirect access from parking lotbrGround floor unit means no elevatorsbrGreat location on the islandbrTwo patios facing North and West for maximum sunset viewsbrDen and Florida Room provide extra space for your group to spread outbrbrMaybe it's time to stop looking and time to start booking.brbrCome To Florida…For The Fun Of It!brbrAll of Pinkie's Properties Have A Few Things In Commonbr• Must Be 25 To Bookbr• No Smoking br• Cancellation OK 30 Days Prior To Check-Inbr• Sheets & Bath Towels Included…BYO Beach Towelsbr• All Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & Foodbr• Basic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More

Catch of the Day at Harbor Towers on Siesta Key

Sarasota, Florida, United States

Bed

Bath

Sleeps

$211.16

Completely private, quiet cottage with 3 Bedrooms & 2 Bathrooms. Centrally located, 5 mins from Main Street and Downtown Sarasota's restaurants. brbrLido Key Beach, Siesta Key + St. Armands Circle & are less than a 15-minute drive. brbr* Samsung 65 TV w Streamingbr* Fast WiFi - 400 Mbpsbr* Weber Grill + Sun Bedsbr* Nest AC Systembr* Large Dedicated Workspacebr* 2 Bikes (Famous Legacy Trail is 2 streets away!)br* Beach Chairs, Umbrella, Towels, Boogie Boardbr* Easy 15 min from the Airportbr* Parking for 2 Carsbr* Pet FriendlybrbrTucked away in a safe and quiet Sarasota neighborhood, this charming private residence offers a peaceful retreat just minutes from the vibrant energy of downtown. Thoughtfully designed with comfort and convenience in mind, the three-bedroom, two-bathroom bungalow pairs the easygoing charm of coastal Florida with modern amenities and inviting interiors. The home’s single level layout and cozy living spaces create an atmosphere that is both relaxed and welcoming, ideal for enjoying a slower pace in sunny Sarasota.brbrInside, the home is outfitted with practical yet stylish furnishings and thoughtful touches. The primary suite features a plush king size bed, a walk-in closet, and a private television, while the second and third bedrooms offer a queen bed and two extra-long twin beds, respectively, each with OEKO TEX® certified mattresses to ensure restful nights. Two full bathrooms, one with a tub and shower, the other with a walk-in shower, accommodate guests with ease. A bright living room with a 65” smart TV and a spacious dedicated workspace add both entertainment and functionality for longer stays or working remotely.brbrOutside, the fenced backyard serves as a private oasis. A screened-in lanai known locally as a “birdcage” features multiple seating areas ideal for al fresco dining or simply lounging under Florida’s sun-dappled skies. The lush garden attracts butterflies, dragonflies, and songbirds, offering a delightful natural backdrop. A Weber grill stands ready for evening barbecues, while two reclining sun beds encourage moments of quiet relaxation. Guests can take advantage of the two adult bicycles to explore the nearby Legacy Trail (2 streets away!), or grab the included beach chairs and head to Lido Key or Siesta Beach for a day on the sand.brbrThe home’s central location is one of its greatest assets. Within a 6-minute drive, guests can access the arts and dining scene of downtown Sarasota, and in under 15 minutes, reach the sugar-white beaches of Lido Key, the boutique charm of St. Armands Circle, or the turquoise shores of Siesta Key. Whether cycling through nature trails, shopping local markets, or enjoying waterfront dining, there’s no shortage of ways to experience the best of this Gulf Coast town. There is also fitness equipment: a yoga mat, 3lb, 10lb + 20lb weight sets + a jumping rope for those who like to keep active on the go. brbr**Pets are allowed for a fee, please pick up after them br**Quiet time after 9pmbr**No loud partiesbr**No smoking allowed on premises or unauthorized guest stays overnightbr*We warmly welcome children of all ages, but please note we do not provide infant equipment. Some features around the house (window blinds and electrical outlets) may not be childproof, so we kindly ask that guests supervise children and take appropriate precautions during their stay.brbrWe try to schedule our groundskeepers when guests aren't staying at our cottage, but in busy season, it's not always possible to do so. As a result, we aim to have the maintenance people on the property on Friday afternoons, and we will do our best to let you know ahead of time, so your visit isn't unexpectedly interrupted.brbrAs a condition of renting this property guest expressly agrees to release, indemnify, and hold harmless the host and any agent of the host from and against all liability for injury to the person of the guest and to any member of his/her party, including any invitees, resulting from any cause whatsoever.brbrCity of Sarasota Registration number: VR24-00104

5 Star ⭐️ Bright, Spacious Home - Downtown, Restaurants, Shopping, Beaches

Sarasota, Florida, United States

Bed

Bath

Sleeps

$591.18

KEEP READING BELOW. THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME. THERE IS VERY USEFUL INFORMATION THAT YOU WON’T WANT TO MISS!!brbrRelax at “Edgewater Escape”, the ultimate waterfront home on Lido Key. This magnificent 3-bedroom, 3-bathroom home offers breathtaking views of the canal and bay and is also the perfect setting for your next vacation. Enjoy Florida’s amazing sunsets by soaking in the hot tub located right on the canal!brbrStep inside and discover the beautifully designed interior, where comfort and style seamlessly blend together. “Edgewater Escape” offers a comfortable and versatile bed configuration to accommodate 6 guests comfortably, but 2 mattresses can extend this up to 8! There are 3 bedrooms and a total of 3 full bathrooms. The sleeping arrangements consist of 3 king beds. Linens are provided, ensuring a restful and enjoyable stay for everyone in your group.brbrThe master bedroom offers a unique and stunning view of the canal while also providing direct access to the patio and hot tub area, allowing you to step outside and relax in the comfort of your own private oasis. On the other hand the kitchen/living room opens up to that same area and overlooks the hot tub, patio, and dock; providing breathtaking views of the tranquil canal. Whether you prefer to unwind outdoors or admire the scenery from the patio, “Edgewater Escape” offers a delightful and immersive experience during your stay.brbrAs you make your way through the home, you'll be drawn to the backyard paradise that awaits you. The backyard is truly the focal point of “Edgewater Escape”, offering a private dock for your relaxation and enjoyment. Spend your days basking in the Florida sun, taking refreshing dips in the ocean and unwind in the soothing waters of Lido Beach.brbrWhen it's time to dine, head to the dining room table, kitchen bar area, or screened-in outdoor lounge area where you can savor your meals in the island breeze.brbr“Edgewater Escape's” location is truly unbeatable. In less than a 2-minute walk, you'll find yourself in the vibrant St. Armands Circle, renowned for its upscale shopping, dining, and entertainment options. And if you're longing for a day at the beach, Lido Key Beach is less than a mile away, offering pristine sands and crystal-clear waters.brbrBook “Edgewater Escape” today and experience St Armand’s Circle and Lido Key at its finest!brbrA SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.brbrwww.vacationDP .(c o m)brbr“Edgewater Escape” can accommodate up to 8 guests with a bedding configuration as follows:br• Bedroom #1: King Bed (1) - Sleeps: 2br• Bedroom #2: King Bed (1) - Sleeps: 2br• Bedroom #3: Queen Bed (1) - Sleeps: 2br• Extra beds: Floor mattress (2) - Sleeps 2brbr***PLEASE NOTE***brbrCOFFEE MAKER: Combo Coffee maker (both drip and K-cups)brbrHOT TUB: The spa is manually operated. Once turned on it can be set to your desired temperature, below 104º.brbrPET POLICY: This home has a $30/pet/day fee. Aggressive breeds (ie. pitbulls, etc) may not be allowed and will need to be approved by management prior to your stay. If you bring your pet without claiming them on the reservation or by trying to avoid paying the pet fee, a minimum fine of $750/pet will be collected. By making this reservation, you agree to this policy. DOGS ONLY. CATS ARE NOT ALLOWED.brbrThe boat dock is not allowed to be used for docking personal or rented boats unless you get approval from management! Penalties will be accessed.brbrVR Cert #: VR25-00113brbrGET TO KNOW THE AREA!brbrExperience the serenity of our world class beaches where you can swim, sunbathe, surf, paddle board, and fish. Take a morning walk down to the soft white sand of Siesta Key Beach or to little Shell Beach to find sand dollars and an assortment of other sea shells. Head to the South side of Siesta key to check out Turtle Beach; a more secluded beach with less people and great surf fishing on the south end.brbrVisit one of the centerpieces of Siesta Key, the AMI City Pier where there is great fishing and plenty of restaurants to choose from. Take a stroll down the Coquina Baywalk and Leffis Key to find a small nature walk with peaceful walking trails.brbrTake the provided bicycles all around the island and search for the 6 beaches that AMI has to offer (can you find them all ); Coquina Beach, Manatee Beach, Bradenton Beach, Holmes Beach, Cortez Beach and Anna Maria Beach (with Bean Point being part of that).brbrOur favorite Anna Maria Island Restaurants:br•Beach House Waterfront (Excellent Seafood)br•Ugly Grouper (Bar/Pub Style Food)br•Waterfront Restaurant (High End Seafood and Steak, Great ambiance)br•Hurricane Hanks (Bar/Burgers)brbrOur favorite Bradenton/Sarasota restaurants:br•KOJO (My personal favorite - High end Asian Fusion)br•Selva Grill (Amazing ceviches and high end courses-Try the KOJO sushi roll and Wagyu Skirt Steak!)br•Owen’s Fish Camp (Unique atmosphere, great seafood)br•Baker and Wife (American, great food)br•SKOB - Siesta Key Oyster Barn (Great happy house and oysters)br•Hyde Park Prime Steakhouse (High end steakhouse)brbrOur favorite Tampa/St Pete restaurants:br•Rococo Steakhouse (High end steakhouse)br•Texas De Brazil (All-you-can-eat Brazilian Steakhouse)br•Bern’s Steakhouse (If you can get a table-amazingly unique eating experience - WORLD FAMOUS)br•Ulele (Local Cuisine, Brew Pub, Michelin Star rated)br•Ocean Prime (High end Seafood)brbrOur favorite Casey Key/Venice restaurants:br•Pop’s Sunset Grill (Ma & Pa style bar and grill)br•Casasariano Italian Eatery (Italian)br•The Breakfast Cottage (Breakfast/Brunch)

Edgewater Escape - 454 “Lido Key”

Sarasota, Florida, United States

Bed

Bath

Sleeps

$263.13

*** Please note that Bay Tree Club requires minimum rental periods of 30 days from January 1 through April 30, or the month of February. Bay Tree Club rules also prohibit guests from bringing animals into the unit. ***brbrbrKick back and enjoy the good life at our lovely condo located on the quiet and peaceful south side of Siesta Key! It's our little slice of paradise!brbrHere you will find a comfortable, well appointed space overlooking a partial view of Little Sarasota Bay, landscaped grounds, and one of Bay Tree Club's two heated pools. Parking, two picnic areas with barbecue grills, and a private cabana stocked with your beach essentials are included. Private access to tranquil Turtle Beach is a short, four-minute walk away - one of the loveliest spots on Siesta Key. You may even see a turtle!brbrExplore the area further using Siesta Key’s free trolley system, which has a stop at the property. You are only four miles away from the number one beach in the country, Siesta Beach! Also nearby are many restaurants, shops, and the popular Siesta Key Village. The greater Sarasota area offers many attractions including the Ringling Museum, Mote Marine Laboratory and Aquarium, Legacy Trail outdoor recreational area, and St. Armands Circle with its upscale dining and shopping.brbrCome and enjoy a serene atmosphere that will make you feel relaxed and at ease during your vacation. We look forward to hosting you at our place.brbrbrWe have a 60-day cancellation policy, but if the property is re-booked for the full term then the guest will receive a refund of 90% of any funds that they have prepaid.

Beautiful 5th Floor Condo with Beach & Bay Access!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$427.78

Perfectly located near the amazing Lido Beach and trendy Downtown Sarasota. Only an 8 minute drive from SRQ Airport & the shops at St. Armand's Circle. Relax on the patio with amazing views of Sarasota Bay. After a day at the beach come home and enjoy the resort-style pool, hot tub, fire-pit, BBQ grills and state-of-the-art gym. This condo is equipped with a full kitchen if you'd like to stay in and enjoy the view, or enjoy experiencing the vibrant restaurant scene. Among all of the amazing things to do in Sarasota there is also a kayak launch offering direct access to Sarasota Bay from the bayou. Our goal is for you to love it here as much as we do and that you will always come and stay. brbrSarasota is the perfect vacation spot. This coastal community offers world class, white-sand beaches as well as an exceptional arts & culture scene. No matter when you visit there are plenty of museums, galleries, gardens, operas, shows and symphonies to see. Sarasota offers many award-winning restaurants, many of which are on the water and/or overlook skylines and downtown(s). The area also offers tremendous options for golfers. Sarasota is home to Mote Marine Aquarium, Marie Selby Gardens, Sarasota Jungle Gardens and Big Cat Habitat so children are sure to love it as well. There are plenty of things to do for everyone.brGuest accessbrOur guests will be able to easily check-in with a personal code for the keypad. This space is brand new and has a large open concept kitchen, dining and living room. The spacious balcony is the perfect spot to relax and unwind with a drink and the sunset. There is a 55 TV in the master bedroom which has a comfortable King size bed. There is also a Queen size sofa sleeper bed in the living room. There is laundry in the unit which is located in the master bathroom. The two smart 55 TV's are set up with Roku and a full cable channel lineup through Xfinity Stream app on Roku.brbrOther things to note:brbr- Upon booking, a signed rental agreement and government-issued photo identification are required prior to receiving an electronic access code to the property.brbrWe love the community at The Strand. Please be mindful and courteous to the neighbors. Our commitment is to give our guests an excellent experience. These are the house rules to help achieve this goal:brbr-$150 HOA-required registration/application fee. (Fee charged after reservation has been made.)br-This property has a minimum primary renter age requirement of 25.br-The designated parking spot is labelled with the unit number.br-This is a waterfront property so take caution.br-Absolutely no climbing on patio railings at any time.br-A/C should not be lower than 70 F and heat should not be higher than 80 Fbr-Set air to 74 degrees prior to checkout. -Please keep sliding doors CLOSED AT ALL TIMES to keep the air inside at a comfortable temperature. *Air-conditioner will sweat if the patio door is left open which will cause issues.br-No lifeguard on duty at the pool. Children must be supervised at all times at the pool area and gym.br-No smoking permitted on premises. $250 fee will be charged if there are any signs/smell of smoking in the house or property.br-Beach chairs are located in our storage unit (instructions in pamphlet). -$150 fee for lost key fobbrbrChecking out instructions:brAll furniture should be as it was found at check in. If you used beach supplies please make sure items are returned to proper location. Trash should be emptied and placed down trash chute across from elevator. Fridge should be cleared out of perishable items. No dirty dishes should be in the sink or surrounding areas. Please hand wash and place on drying rack or rinse and leave before put in dishwasher. Please place dirty towels in basket and hang if wet. We pride ourselves for having a clean and welcoming environment for all our guests .We appreciate your respect of our family unit and hope you enjoyed your stay at our property.brbr*As per association rules there are to be no company trucks with logos or trailers in the parking lot of the property. brbr

Condo Cuteness with Stellar View ~ On The Water Perfectly Located

Sarasota, Florida, United States

Bed

Bath

Sleeps

$591.27

Roomy contemporary single family home in the heart of St. Armand's Key available for monthly rental with discounts for longer stays. brbrThis high end turnkey home is furnished and outfitted with everything you will need except food and clothes. It is a storm safe elevated concrete structure served by an interior elevator as well as an atrium style wrapping staircase. Sliding walls and floor to ceiling glass on both the north and south sides open the living spaces and primary bedroom onto railed Julliet style balconies overlooking the pool to the rear and Sarasota Bay to the front.brbrA large open floor plan on the living level includes living, dining, a den area, powder room, recently updated kitchen with induction range and three door refrigerator and breakfast nook with sliding glass doors. brbrAll bedrooms are on the second level, each with an en suite bath. There is also a fully equipped laundry area on the second level. The primary bedroom has a king sized bed, large walk in closet, floor to ceiling windows and an on suite bathroom with double sinks, and a large shower. The first guest bedroom has a king sized bed and en suite bathroom with shower. The second guest bedroom has a queen sized beds and an en suite bathroom with a tub/shower combination. brbrThere is a two car garage, half bath, plus outdoor shower on the entry level. The flooring in the home is marble, wood and carpet in the bedrooms.brbrThe backyard is a lush, tropical, private oasis with gorgeous landscaping and a heated lap pool. The owner will consider a small dog with a monthly rent premium. brbrOwner includes grounds keeping, weekly pool servicing and Xfinity broadband with smart TVs and will pay utilities to a cap and the guest pays all overages. brbrWalk to Lido Beach, St. Armand's Circle, and many restaurants and shops.

St Armands Key Walk to Beach - 3 Bedrooms 4+ Bathrooms Private Heated Pool

Sarasota, Florida, United States

3

Bed

4

Bath

7

Sleeps

$317.75

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.brbrVR24-00130

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Sarasota, Florida, United States

3

Bed