Vacation Rentals By Owner In Sarasota, FL

Enjoy a relaxing stay in this beautiful property just minutes from the most beautiful beaches on Florida's west coast. This cozy house combines comfort, style and an unbeatable location, ideal for family vacations, romantic getaways or trips. It has a large living room with natural light, a fully equipped kitchen, comfortable bedrooms and a private patio perfect for enjoying the weather.

The Tree House 5 min to beach, airport, Downtown

Sarasota, Florida, United States

Bed

1

Bath

6

Sleeps

$207.86

Newly renovated!! Escape to paradise in this charming two-bedroom, two-bathroom condo located at the serene south end of Siesta Key, Florida. Nestled just steps away from the Blind Pass Lagoon, this vacation rental offers the perfect blend of comfort and coastal charm.brInside, you'll find a spacious living area with bedrooms at either end of the condo perfect for privacy. The fully equipped kitchen is ideal for preparing meals to enjoy in the cozy dining area or on the private screened-in balcony.brThe primary bedroom features a king-sized bed and an en-suite bathroom while the second bedroom offers two twin-sized beds and easy access to the guest bathroom with a shower/tub combination.brWhether you're watching dolphins play in the gulf or enjoying breathtaking sunsets from your balcony, this Siesta Key condo promises an unforgettable vacation experience. Perfect for families, couples, or friends, it's your gateway to the ultimate coastal getaway.

Charming condo with water views located at the south end of Siesta Key

Sarasota, Florida, United States

Bed

Bath

Sleeps

$133.47

Heritage Oaks, a private gated golf & tennis country club community in Sarasota, Florida. Our Condo is located on the signature 14th Hole with views of the lake and golf course. Situated on the 2nd floor, it features vaulted ceilings, 2 bedrooms, 2 baths, and 2 screened Lanai’s. The master bedroom has a king size bed and walk in closet, while the second bedroom has 2 twin size bed which can be converted to 1 king size bed.brbrThe clubhouse offers wonderful dining, including a pub style grille room. There are many organized events. There is a complete exercise facility in the main clubhouse.brbrGated, private golf course community. Five heated pools, fitness center, tennis, and restaurants. Heritage Oaks Golf and Country Club has a mandatory registration membership transfer fee of $300.00. Membership entitles the guest to use the golf course, driving range, tennis, swimming pools, fitness center, restaurant, social and other facilities of the country club. brbrAdditional Golf fees apply.br18 holes $65 which includes cart and taxesbr9 holes $33.25 which includes cart and taxesbrbrhttps://www.youtube.com/watch v=QCEDYy6TiMQbrbrBeautiful Siesta Key beach is just a short drive from Heritage Oaks. Sarasota is famous for its downtown fine dining, art galleries, theater and concerts. brbrHeritage Oaks is conveniently located just a short distance off I-75, about 20 minutes from the Sarasota airport, and about an hour from Tampa International airport.brbrThis is a non-smoking condominium and we do not allow pets of any kind.

Heritage Oaks 2 Bedroom with Golf Course and Water Views

Sarasota, Florida, United States

Bed

Bath

Sleeps

$321.72

Experience the beauty of Poolside Oasis in this modern 3 bedroom, 2 bath private pool home in Sarasota. Enjoy shopping and dining in nearby Siesta Key, Lido, St. Armands and downtown Sarasota! The home is in a central location close to either the north or south bridge to the Siesta Key beaches and Village. One small dog is allowed with pet fee.brbrPeaceful pool and pond views from almost every room in the house. You will be living the Florida lifestyle in this 1,929 sq. ft. spacious home with a split bedroom floor plan. The primary ensuite bedroom on one side and the two bedrooms and one bathroom on the other side of the house. The primary ensuite bedroom features a walk-in closet and the adjoining bathroom has double sinks along with a walk-in shower. The two bedrooms on the opposite side of the house provide ample privacy and share a modern bathroom with a walk-in shower. Relax and listen to music or watch TV in the living room with a large smart TV or in the family room with another large smart TV. Multiple sliding glass doors open out to the large inviting pool.brbrEnjoy cooking and socializing in the updated kitchen with quartz countertops, stainless steel appliances including a refrigerator, microwave, stove/cooktop and dishwasher. Dining is easy whether it's casual at the breakfast bar or at the indoor dining table next to the kitchen. Across from the kitchen, family room adjacent is a wet bar and mini fridge, plus a Keurig and standard coffee pot for the morning ritual. Just outside the sliding glass doors of every pool facing room is the screened in pool area with plenty of room for lounging or entertaining including a dining table that seats 6 and BBQ Grill. Listen to music or watch your favorite game on the large smart TV out by the pool. Inside the house is a separate room with a washer and dryer that leads to the garage where you will find beach chairs, beach umbrella and beach wagon to explore the local beaches.brbrThis home is located in a peaceful residential neighborhood and at the same time close to so many restaurants and shopping. Siesta Key Beach is only 6 1/2 miles away where you can experience the World famous soft quartz crystal sand beach. After beaching all day you can check out the casual tiki bars, gourmet dining establishments and local shops in Siesta Key Village. Siesta Key Village has a farmers market every Saturday from 9AM to 2PM. Or check out the larger downtown Sarasota Farmers Market from 7AM to 1PM on Sundays. Enjoy Historic downtown Sarasota starting about 5.5 miles away where you will find boutiques, gift shops, art galleries, local casual and fine dining restaurants, the Selby Botanical Gardens, concerts at the Van Wezel Performing Arts Hall, Sarasota Opera House to name a few. Downtown Sarasota always has activities during the holidays including a Pineapple Drop on New Years Eve, seafood and art festivals. A little further north is St. Armands Circle where you will find more local shopping and dining and food festivals. This home is a dream come true to anyone looking for easy living with plenty of space and modern amenities. One small dog allowed in the home. brbrThis home has cameras around the perimeter of property, a video doorbell and one camera in the pool area for security and insurance purposes.

Poolside Oasis - Modern spacious 3 bedroom, 2 bathroom private pool home in Sarasota near Siesta Key

Sarasota, Florida, United States

Bed

Bath

6

Sleeps

$316.4

Welcome to your perfect Sarasota escape! This beautiful home offers comfort, and an unbeatable location. Only a 10-minute drive from the beach,the Gulf Coast and relaxing evenings in a peaceful neighborhood.brInside, you’ll find a bright and inviting space with modern décor, fully equipped kitchen, comfortable bedrooms, and everything you need for a stress-free stay. Relax on the patio, take a short drive to Siesta Key, Lido Beach, St. Armands Circle, and downtown Sarasota

Discovery Cove with four bedrooms and two bathrooms

Sarasota, Florida, United States

4

Bed

Bath

8

Sleeps

$119.47

This two bedroom, two bath condo is ***AVAILABLE STARTING NOVEMBER 2025, DECEMBER 2025 AND JANUARY 2026*** Welcome to WINDSOR LODGE AT THE OAK community. It's gated 24/7 and as private as private can be. Drenched in value and a fantastic community located in South Sarasota. This unit has an open floor plan, easy to show! Close to Siesta Key, Costco and a variety of restaurants. Very convenient to all the amenities Sarasota has to offer.

Windsor Lodge at the Oaks 1

Sarasota, Florida, United States

Bed

Bath

Sleeps

$1338.05

This unique retreat in the heart of St Armand's Circle was just freshly renovated and ready for fun! Stroll to pristine beaches or enjoy the vibrant shops & eateries of St. Armand's Circle just steps away! Boasting 3 beds, 2 baths, a bonus room, sparkling pool, sun-soaked deck gorgeous garden - have it all and with brand new luxurious finishes.brbrThis area of Sarasota allows for weekly stays, per City ordinance. 26-VR-000001

St Armands Mid Century Rad Pad with Pool

Sarasota, Florida, United States

Bed

Bath

Sleeps

$1207.97

Mid-century retreat in the heart of Lido Key! Stroll to pristine beaches or enjoy the vibrant shops & eateries of St. Armand's Circle just steps away! Recently renovated with authentic period details, this 3BR/3BA gem boasts an expansive sparkling pool, sun-soaked rooftop deck and stylish office. Other unique features - a handmade bar with equipment for entertaining, original refinished Terrazzo floors, plenty of parking, new travertine patio, lots of natural wood! This area of Sarasota allows for weekly stays, per City ordinance.brbrVR2400013

St Armand's Circle Mid-Century Oasis with Pool - Steps to Circle

Sarasota, Florida, United States

Bed

Bath

6

Sleeps

$301.08

Relax in this inviting Sarasota getaway, conveniently located just minutes from Siesta Key Beach. With a private backyard, modern furnishings, and thoughtful comforts throughout, this 3 bedroom home offers the ideal setting for a laid-back Florida stay.brbrKey Features:br3 Spacious Bedrooms – Sleeps up to 7 comfortably, perfect for families or group getawaysbrPrivate Heated Pool – Enjoy swimming and lounging year-round in your own backyard oasis. Heating additional charge.brClose to Siesta Key Beach – Just a short drive to world-famous white sands and turquoise watersbrBeach Gear Included – Towels, chairs, umbrellas, and a cooler—all ready for your beach adventurebrFully Equipped Kitchen – Modern appliances and cookware to make meals at home a breezebrOutdoor Entertainment Area – Covered patio with dining space and grill, great for evenings outsidebrBright & Modern Interiors – Stylish decor with comfortable furnishings and plenty of natural lightbrHigh-Speed WiFi & Smart TVs – Stay connected and stream your favorites with easebrWasher & Dryer On-Site – Convenient for longer stays or family vacationsbrPrime Sarasota Location – Near shopping, dining, golf, and local attractionsbrbrThis home offers the perfect blend of tranquility and convenience. This quiet Sarasota community is known for its tree-lined streets, well-kept homes, and relaxed, welcoming vibe—making it ideal for families, couples, and groups seeking a restful Florida escape.brbrGuests love the prime location—you're just minutes from the soft white sands of Siesta Key Beach, consistently ranked among the top beaches in the U.S. Enjoy easy access to local dining, boutique shopping, and a variety of cultural attractions, including The Ringling Museum, Marie Selby Botanical Gardens, and vibrant downtown Sarasota.brbrOutdoor enthusiasts will appreciate nearby parks, walking trails, and golf courses, while everyday essentials like grocery stores, coffee shops, and pharmacies are just around the corner.brbrWhether you're planning a beach vacation, a remote work retreat, or a family reunion, Greenbrook Drive places you right in the heart of all Sarasota has to offer—without the hustle and bustle.brbrIf you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you.brThe Bay and Key Collection offer a wide range of services including:br- An any day arrival policy and length of stay requirements starting at just 7-nights.br- We have a professional property manager and maintenance systems meaning you'll experience the service you deserve.br- Professional housekeeping pre-stay and during stay if requested.br- 'Guide Books' allowing you to be able to add experiences to your itinerary and see some of our recommendations.br- 'Preferred Vendors' meaning you can trust the company you use for rentals.brAll properties listed with The Bay and Key Collection benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.brbrProperty Description:brWelcome to this inviting 3-bedroom Sarasota retreat, ideally located just minutes from the white sands of Siesta Key Beach. Designed for families and groups, this spacious home offers a private pool - perfect for unwinding after a day in the sun. With modern amenities, a fully equipped kitchen, and easy access to local attractions, dining, and shopping, this home provides the ideal setting for a relaxing Florida getaway.brbrExternal:brStep outside to your private pool and patio, complete with outdoor seating and a dining area - perfect for grilling, entertaining, or enjoying a peaceful morning coffee. The covered lanai provides shade and comfort, allowing you to enjoy the outdoor space in any weather.brbrWhile Lampiasi Street itself is a quiet residential street with gated facilities, the surrounding Palmer Ranch area offers an exceptional community atmosphere known for safety, walkability, and proximity to local amenities.brbrGuests will enjoy:br• Safe, walkable streets great for morning strolls, jogging, or bikingbr• Nearby public parks like Gulf Gate Community Park and Legacy Trail for walking, biking, and outdoor activitiesbr• Access to top-rated golf courses and tennis clubs within a short drive (like TPC Prestancia and Serendipity Racquet Club)br• Quick access to shopping centers, grocery stores, and casual or fine diningbr• Close to public beaches, nature preserves, and cultural venues in central SarasotabrbrWhile there are no formal shared community facilities on this home itself, the home’s prime location places you within minutes of everything Sarasota has to offer—without sacrificing peace and quiet.brbrProperty can be accessed via key lock box located at the property, code is sent on the day of arrival. brbrDirections: brTake Exit 205 for FL-72/Clark Road toward Sarasota. Head west on Clark Road (FL-72) for about 4.5 miles. Turn left onto Honore. Continue on Honore Road for about 1.5 miles. Turn right into Esplanade on Palmer Ranch.brbrParking is available on site for a maximum of 2 cars in the driveway. Parking is not available on the street. brbrPer HOA Regulations - This property must be rented for a minimum of 30 nights. If the travel dates you are looking for don't appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.brbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions. brbrAccidental Damage Insurance: Accidental Damage Insurance is included within all guest stays at The Bay and Key Collection.brbrGuests must cancel at least 60 days before check-in to receive a full refund for all nights, minus a 10% processing fee.brGuests must cancel at least 30 days before check-in to receive a 50% refund for all nights.brIf a guest cancels less than 30 days before check-in, you'll be charged 100% for all nights.brWe strongly recommend that you purchase your own travel insurance for your protection.

Esplanade Getaway - Luxury 3 Bed Pool Home by The Bay & Key Collection

Sarasota, Florida, United States

Bed

Bath

Sleeps

$642.76

Summary:brbrWelcome to the Arlington Ocean Oasis, a modern and luxurious rental property offering an unparalleled coastal experience. This spacious 5 bedroom, 5 bathroom retreat boasts two primary suites, ensuring privacy and comfort for all guests. With living room spaces on two floors, there's ample room for relaxation and entertainment. Step outside into the glorious backyard, where a heated saltwater pool awaits, inviting you to bask in the sun or take a refreshing dip.brbrbrbrThe Space:brbrWelcome to Arlington Ocean Oasis, your private retreat in the heart of Sarasota—just minutes from the soft sands of Lido Key and Siesta Key Beach.brbrbrbrInside, you'll find a modern, fully equipped chef’s kitchen designed to inspire—from morning coffee to multi-course meals. Stocked with high-quality cookware, utensils, and gadgets, this kitchen is ready for anything from a quiet dinner for two to a family-style feast.brbrbrbrStep outside and channel your inner grill master with the outdoor BBQ grill or take things up a notch using the Big Green Egg—perfect for creating unforgettable flavors during warm evenings.brbrbrbrWe’ve got your beach days covered with beach chairs, shade tents, coolers, toys, shovels, and ice packs—just pack your sunscreen and you’re set.brbrbrbrAfter a day at the beach, unwind in style or explore the nearby shopping and dining scenes of downtown Sarasota, only minutes away. From local art galleries to cozy cafes and upscale restaurants, you’ll find something to match every mood.brbrbrbr- Planning a quick getaway or a longer stay We understand that every trip is different—reach out to us directly if your dates don’t match our minimum stay. We’re happy to be flexible when we can!brbrbrbrArlington Ocean Oasis blends comfort, convenience, and a touch of luxury—perfect for couples, families, or small groups. We look forward to hosting you!brbrbrbrThe Neighborhood:brbrLocated in the historic Arlington Park areabrbrbrbrGetting Around:brbrQuick access to Tamiami Trail and Bahia Vista St.brbrbrbrOther Things to Note:brbr* Primary Guest must a minimum of 25 years old and present during the entire staybrbr* Only registered guests may be on the propertybrbr* NO PARTIESbrbr* Quiet hours strictly enforcedbrbrbrbrSTARTER SUPPLIES: We offer a starter supply of toiletries and cleaning/laundry supplies.brbrbrbrCANCELLATIONS, CHANGES, AND REFUNDS. brbrAll bookings are subject to the following cancellation policy:brbrbrbr1. PMI Sarasota Permitted Cancellation Periods:brbra. 30 days or more prior to your check-in date for rental periods of 7 days or lessbrbrb. 60 days or more prior to your check-in date for rental periods of 8 days or more brbrbrbrYou may cancel your booking according to either a. OR b. above, given by written notice (email accepted with time-stamp) to PMI Sarasota. If the cancellation meets the criteria of either a. or b. the full amount of your reservation deposit will be refunded, less a $200 cancellation fee and any non-refundable charges including booking fees and management/admin fees.brbrbrbr2. All refunds, whether in whole or pro-rated, will be subject to the deduction of third party non-refundable charges.brbrbrbrFor cancellations made after the Permitted Cancellation Periods above, Guest is responsible for the full amount of the total booking charges. Guest’s only recourse for refund after the Cancellation Period is a claim on a previously purchased vacation travel insurance policy. To protect against loss of your advance deposit or booking payment resulting from cancellations caused by certain unforeseen events, such as illness, death, natural disasters, etc., we recommend that guests purchase Vacation Travel Protection Insurance.brbrbrbrThis Property is registered with the City of Sarasota under Certificate #VR25-00086.

Arlington Ocean Oasis 5br 5ba Htd Saltwater Pool

Sarasota, Florida, United States

5

Bed

4

Bath

10

Sleeps

$198.84

Summary:brWelcome to your modern Sarasota retreat! This fully renovated 4-bedroom, 2-bathroom home is beautifully designed to blend style, comfort, and convenience. Relax by the saltwater heated pool and spa, enjoy evenings under the screened lanai with an outdoor TV, and experience all the best beaches, dining, and attractions Sarasota has to offer. Whether you're here for an extended getaway, or a remote work stay, this home is your perfect Florida escape.brbrThe Space:brThis spacious home features nearly 2,000 square feet of modern living space with a clean, neutral design palette. The open floor plan connects a large living room, a gourmet kitchen with stainless-steel appliances and a breakfast bar, and a dining area that comfortably seats six. The primary suite offers direct pool access, a king bed, and a spa-like ensuite bathroom. Two guest bedrooms each have queen beds, and a fun kids’ bedroom offers a twin bunk and trundle. With Smart TVs, high-speed WiFi, and plenty of room to gather indoors and out, this home is designed for comfort and relaxation.brbrGuest Access:brGuests will have full private access to the entire home, garage, driveway, saltwater pool, and spa. You'll also have access to beach gear located in the garage, including chairs and a cooler. Entry is keyless — a personalized code will be provided on the morning of your check-in. The garage can be accessed via a separate code, making coming and going easy and secure throughout your stay.brbrThe Neighborhood:brLocated in the heart of Sarasota, this home offers the perfect balance of quiet neighborhood charm and proximity to the area’s top attractions. You'll be just a short drive from Siesta Key Beach, Lido Key, St. Armands Circle, and downtown Sarasota. Local restaurants, grocery stores, golf courses, and parks are all nearby, making it easy to enjoy everything Sarasota has to offer while coming home to your own private oasis.brbrGetting Around:brWhile having a car is recommended to fully explore Sarasota and the surrounding Gulf Coast beaches, rideshare services like Uber and Lyft are readily available. Downtown Sarasota, Siesta Key, and shopping areas like University Town Center are all within a 10–20 minute drive. Ample parking is available on the property, with space for multiple vehicles in the driveway and garage.brbrOther Things to Note:brPool heating is available for additional fees. Please let us know in advance if you would like it turned on.brExterior security cameras are in place for safety at the front door and driveway — no cameras are inside the home.brTrash pickup is every Wednesday; please place bins out Tuesday evening.brBeach gear is provided in the garage for your convenience, and we ask that you rinse off equipment before returning it.brWe offer a fully stocked kitchen and laundry area, making this an ideal spot for longer stays!brTourist taxes are removed on stays over 6 months.brAdditional damage waiver fees incur for stays over 40 daysbrbrInteraction with Guests:brWe respect your privacy but are always just a message or phone call away! Our local management team is available to assist if you need anything during your stay, from restaurant recommendations to troubleshooting. We want you to feel at home and enjoy a seamless, stress-free experience.

Relaxing 4BR Home with Saltwater Pool/Spa, Near the Beach, 30 day minimum, perfe

Sarasota, Florida, United States

Bed

Bath

Sleeps

$173.08

Wonderful 1Br 1st floor condo on the bay side with privatebrGulf side beach access! This condo has a full kitchen with everything you could want. There is also a 42' flat screen tv in the living room. It has a leather sleeper sofa. The bedroom has a king size bed with a full dresser and a tv. The bathroom has a tub/shower. There is a nice little front porch where you can sit outside and enjoy the wonderful weather. There is also a fenced in back porch area for privacy. Enjoy the community pool, community grilling area, fishing pier, bocci ball, and relaxing grass area to sit back and watch all the boats go by. The people here a very friendly. There's a real community spirit here.brThe complex will not allow pets, motorcycles, trailers, or RV's of any type.br

BEST OF BOTH WORLDS! Fish in the bay or walk across the street to the beach!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$167.61

Rustic, romantic and full of personality, this period cottage has all the allure and character of long-ago Florida overflowing with new, modern, comfy amenities.brbrThe flowers are in bloom! Make yourself at home in this cozy, quaint, 1920's Old Florida Guest House. Nestled under a canopy of ivy-covered oaks, pines and everyone's favorite Florida palms. This captivating cottage is your woodsy home base for all your Sarasota adventures!brbrThis lovely little cottage is very private & isolated. The cottage is located on a secluded GATED property offering you total security, privacy and exclusivity.brbrFully equipped kitchen with brand new cabinetry and counters, full-size appliances, a full compliment of cookware, dishes, utensils and supplies. Coffee & Tea makers for your morning pick-me-up are at the ready.brbrWhether grabbing a quick bite before heading off on your day on the water or in the museums, or gathering for a quiet evening meal at home, your kitchen essentials are all here!brbrBathroom feature a spa-like walk-in shower, high-end fixtures & features, in soothing & peaceful blues and grays to complete your cottage experience. brbrCharming private & cozy backyard with ground-level deck, dining/seating & BBQ grill with direct access from cottage through a full-lite glass door which brings the sunlight and greenery practically inside. Enjoy the warm Florida days or star-filled evenings on your secluded deck.brbrFor the business traveler, light packer, or long-term visitor, you can be assured all the necessities are at your disposal. Luxurious towels, iron & ironing board, hair dryer, computer desk, wi-fi, loads of closet space and access to full-size washer & dryer. brbrThe bedroom welcomes you to its Queen size memory foam mattress and the living room offers a gorgeous Queen size sofa bed.brbrThe Cottage has beach chairs, beach umbrellas and even insulated beach cups all for your use and convenience. brbrCable TV, Internet, WiFi & 43 TV to keep you connected and entertained.brbrFree Cable TV, NETFLIX, Amazon Prime Video included!brbrElectrolux Washer & Dryer set available for your use.

Guest House

Adorable 1920s Cottage in a Tropical Wooded Setting!

Sarasota, Florida, United States

Bed

Bath

Sleeps

$313.34

Enjoy nature and everything Sarasota! br• Refreshing breezes of private wrap-around deck perched above 2 acres of Real Florida. br• Most pets welcome**br• Comfortable beds & many USB ports.br• Towels; bedding; fully equipped kitchen br• Bikes, portable-crib, 1st day cont breakfastbr• Boat/truck/RV parking (ask permission/pricing) br• Air conditioned rooms; plenty of hot waterbr• Special occasions* br• EV Charging Station (ask if it matters)br• Secluded, yet close enough to enjoy Lido & Siesta Key beaches, events at Benderson Park, plus 5-star shopping & dining of University Town Center. br• Pool & fitness center: ask for a status updatebr• Sleeps comfortably 1-12, up to 24 nice people (“if you really love each other”). We provide extra comfy mattresses on floor, couch, pull out sofa bed, air mattresses or wherever you can fit (upon requested need)br• 1400 ft.² Elevated accommodations (2nd floor) brbrNOTES:brPrior to 2022 our Tropical Escape had been most wish-listed, with 345 reviews (4.82/5.00). We can provide those reviews upon request - we no longer do business with that company.brbrWe look forward to hosting your Tropical Escape in Sarasota, Florida !brMichaelbrbr* We love hosting special occasions, celebrations, family reunions, and more. Ask for special pricing and packages. brbr** Pet fees are per pet, and charged by weight. Unattended pets may incur roaming fees if uncrated. Please ask for pet policy and pricing details before booking.

Discover Real Florida UP CLOSE! Tropical Escape Sarasota

Sarasota, Florida, United States

Bed

Bath

Sleeps

$221.42

Summary:brbrWelcome To The Strand, Where Luxury Living Meets The Gorgeous Waterfront Of Downtown Sarasota. A gated waterfront community, just steps from downtown Sarasota, with direct Gulf access.brbrbrbrThe Strand is Sarasota’s newest community of luxury condominium waterfront living. Close to restaurants, beaches, shopping districts, and much more. The Strand residence have direct access to the Gulf and you can enjoy beautiful Sarasota sunsets or the bay front.brbrbrbrThe Space:brbrFully furnished 2BR, 2BA waterfront unit. Kitchen is set up for everything you will need for your stay. We provide guest access to 2 kayaks during your stay. In addition to the fabulous surroundings of Downtown Sarasota, the local area has a wealth of delightful restaurants, cafes and bars that are just a stone’s throw away from our condos. From fresh seafood shacks to bar and grills that cater for all tastes, you will definitely find what you are looking for. You will be on the doorstep of more than just the finest restaurants and bars, there is a huge variety of pastimes for you and your family to indulge in, no matter age or ability. Make the most of the glorious water and charter boats to relax away from the land. For the more adventurous, there are lots of adrenaline fuelled water sports to play including parasailing and under water activities such as snorkelling and scuba diving. brbrbrbrBack on dry land, you can entertain the family in a number of ways. You can rent the very best bikes to explore the amazing landscape on view in Sarasota, be sure to stop on your cycles to visit more exciting places like cigar and wine bars, massage parlors, health spas and more.brbrbrbrGuest Access:brbrSet off for a day on the crystal clear waters in your very own kayak, included to use at no charge. Feel free to bring your own paddle board or kayaks as well. You can launch from the kayak launch and get your friends and family active.brbrbrbrThe stunning boardwalk spans 1000 square feet and offers wonderful views of the entire waterfront. Enjoy a luxurious day of fishing, have a stroll and take in the views and enjoy the sunset over the waterfront. The boardwalk is the perfect setting for a romantic meal as well as a prime fishing location for some quality alone time.brbrbrbr1 car per unit is allowed for entry.brbrbrbrGetting Around:brbrNavigating downtown Sarasota is a breeze, offering a seamless blend of convenience and charm. Whether you prefer to explore on foot, by bike, or via public transportation, downtown Sarasota has you covered. The city boasts pedestrian-friendly sidewalks, perfect for strolling amidst the vibrant streets lined with boutiques, cafes, and cultural attractions.brbrbrbrFor cycling enthusiasts, dedicated bike lanes and picturesque paths make it easy to pedal your way through the city. Embrace the coastal breeze as you ride along scenic routes and discover hidden gems around every corner.brbrbrbrPublic transportation options, including buses and trolleys, provide efficient and accessible ways to traverse downtown Sarasota and its surrounding areas. Enjoy the ease of moving from one district to another, experiencing the diverse offerings of this lively city.brbrbrbrWhether you're drawn to the cultural landmarks, shopping districts, or waterfront vistas, getting around downtown Sarasota is a delightful journey, inviting you to explore the heart of this vibrant Florida city with ease.brbrbrbrOther Things to Note:brbrBlackout windows for great sleep. To ensure a smooth and comfortable start to your stay, we provide an initial setup of supplies designed to last approximately 2 to 3 days. This thoughtful arrangement allows you ample time to settle in and get acquainted with your surroundings before embarking on any shopping adventures. From essentials to enhancing your convenience, we've taken care of the basics, so you can focus on enjoying your time in our welcoming space.brbrbrbrInteraction with Guests:brbrText is best. Very responsive.

Villa

Stunning Water View, Kayaks, Resort Pool Sarasota

Sarasota, Florida, United States

Bed

Bath

Sleeps

$1360.46

Luxury Sarasota Waterfront Rental | 5-Level Modern Home on Sarasota Bay | Private Dock & Rooftop TerracebrbrEscape to The Solstice House, a luxury Sarasota waterfront rental designed by award-winning architect Michael Halflants. Located directly on Sarasota Bay at the mouth of Bowlees Creek, this five-level modern masterpiece offers panoramic bay views, a private dock, and exceptional indoor-outdoor living.brbrAvailable for exclusive weekly rentals, this private waterfront home is ideal for snowbird rentals in Sarasota, extended family stays, or summer luxury vacations on Florida’s Gulf Coast.brbrSarasota Bay Waterfront LivingbrbrPositioned directly on the water with sweeping Sarasota Bay views, The Solstice House captures waterviews and sunrise and sunset from nearly every room. The expansive rooftop terrace offers dramatic 270-degree water views — one of the most unique vantage points in Sarasota.brbrEnjoy:brbrPrivate waterfront dock with fishing accessbrbrKayaking directly from the propertybrbrDolphin and manatee sightings in Sarasota BaybrbrMultiple waterfront terraces and outdoor seating areasbrbrThis is true Sarasota waterfront living — private, quiet, and minutes from everything.brbrSpace Designed for Luxury & ComfortbrbrThis modern luxury vacation rental in Sarasota includes:brbr3 spacious bedroomsbrbr2 private offices (perfect for remote work)brbr4.5 bathroomsbrbrFully equipped gourmet kitchenbrbrPrivate gymbrbrGame roombrbr5 levels of architect-designed living spacebrbrGarage parkingbrbrPerfect for families seeking a luxury snowbird rental in Sarasota or guests wanting a high-end waterfront retreat near Siesta Key and St. Armands Circle.brbrPrime Location – Minutes to Sarasota’s Bestbrbr10 minutes to Downtown Sarasotabrbr15 minutes to St. Armands Circlebrbr25 minutes to Siesta Key BeachbrbrQuick access to Longboat Key beachesbrbrClose to IMG Academy, golf, fine dining, boating, and cultural attractionsbrbrEnjoy the privacy of a Sarasota Bay waterfront home while remaining close to world-class beaches, restaurants, and shopping.brbrIdeal For:brbrSnowbirds seeking a luxury Sarasota seasonal rentalbrbrFamilies wanting a private waterfront vacation homebrbrGuests who appreciate modern architecture and panoramic bay viewsbrbrActive travelers looking for boating, fishing, kayaking, and cyclingbrbrAmenitiesbrbr5-Level Luxury Waterfront HomebrbrSarasota Bay Views from Nearly Every RoombrbrExpansive Rooftop Terrace with 270° Water ViewsbrbrPrivate Dock & Kayak Access (owner's boat is stored on the lift)brbrPrivate Gym & Game RoombrbrHigh-Speed InternetbrbrAll Utilities IncludedbrbrWeekly Waterfront Rental Availability

Exclusive 5-Level Waterfront Solstice House on Sarasota Bay

Sarasota, Florida, United States

Bed

Bath

Sleeps

$142.23

Enjoy the perfect Florida getaway in this beautifully appointed 2-bedroom, 2-bath first-floor condo located in a sought-after golf course community. Just 15 minutes from the sugar-sand shores of Siesta Beach and Nokomis Beach, this home offers the best of coastal living and resort-style amenities.brbrThe lushly landscaped community features pools, tennis courts, and a clubhouse with an on-site restaurant, all included with the transfer of social membership. Inside, the spacious primary bedroom offers a comfortable queen bed, while the second bedroom features custom triple-tier full bunk beds—making this home ideal for families and groups, comfortably sleeping up to 8 guests.brbrRelax on the cozy screened porch overlooking a peaceful nature preserve, or enjoy the updated kitchen with stainless steel appliances. Additional conveniences include designated covered parking and a private storage unit stocked with beach essentials.brbrWith a beautifully redesigned golf course and everything you need for a relaxing winter retreat, this condo is the perfect home away from home.br30-day minimum rental required.

Beautiful condo in Sarasota's Stoneybrook Country Club

Sarasota, Florida, United States

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Bath

Sleeps

$418.48

Welcome to Casa Azul! This luxury property accommodates up to 8 and is 10 minutes to Siesta Key Beach (#1 Beach in America), 15 minutes to Downtown Sarasota & The Marina. 20 minutes to SRQ Airport. 20 minutes to Lido beach, St. Armands Circle & Long Boat Key. World class restaurants, Shopping, Tiki Bars and entertainment just minutes away.brbrIndulge in the epitome of luxury with Casa Azul, a sprawling sanctuary nestled in an exclusive residential enclave in Sarasota.This opulent retreat boasts newly curated furnishings, a grandiose kitchen, and an expansive open concept living area, promising a stay of unparalleled comfort and sophistication.brbrSituated just minutes from the world famous Siesta Key Beach, and a short drive to downtown`s vibrant attractions, Casa Azul offers unrivaled convenience without compromising on tranquility. Immerse yourself in the area`s finest dining, shopping, and entertainment options, creating cherished memories with loved ones in this premier destination.brbrStep into a world of refinement as you explore Casa Azul`s meticulously designed interiors. The spacious living room features sleek porcelain tile flooring, complemented by an oversized leather sectional sofa, providing an inviting space to unwind. Adjacent, a private seating area offers a cozy retreat, while a state-of-the-art 75` TV promises cinematic experiences.brbrChannel your inner chef in the gourmet kitchen, equipped with top-of-the-line stainless steel appliances and elegant granite countertops. The expansive peninsula bar with seating for four invites you to savor culinary delights in style. Enjoy casual meals in the charming breakfast nook, bathed in natural light, or gather around the modern rustic dining table for eight, recounting the day`s adventures.brbrRetreat to the primary bedroom, a haven of tranquility featuring a sumptuous king-size bed, a chaise lounge for moments of repose, and a private workspace for added convenience. The ensuite bathroom exudes spa-like luxury, boasting a freestanding clawfoot tub, dual vanities, and a spacious walk-in shower, ensuring a rejuvenating experience.brbrBedrooms #2 and #3 offer plush king-size beds and thoughtful amenities, while the hall bathroom, shared between the rooms, features an oversized vanity and a walk-in shower. brbrEach bedroom is equipped with Smart TVs for entertainment and black out window shades.brbrAs a bonus, the home has 2 premium roll away beds for extra guests. brbrOutdoors, Casa Azul invites you to unwind in style. Lounge in the newly constructed lanai patio, complete with a heated pool and hot tub, offering the perfect setting to admire Florida`s spectacular sunsets. The kids will love frolicking in the large shallow splash pad.brbrGather around the fire table, or enjoy a family barbecue with the provided grill, creating lasting memories under the starlit sky.brbrExperience the ultimate in luxury living at Casa Azul, where every detail has been thoughtfully crafted to elevate your vacation experience.brbrOutdoor AmenitiesbrbrYou’ll love the big yard, with mature native trees, as well as a privacy divider between you and the neighbors. There’s nothing behind you, so your view is simply the beauty of the natural world. Soak in the evening sky with its ever-changing colors relaxing in your very own backyard oasis. brbrIn the garage, guests will find plenty of beach supplies, including beach cruiser bikes, beach toys, beach wagon, floats, cooler, umbrella, and beach chairs. The front-loading washer and dryer is also located here.brbrOther things to note:brbrNeighborhood & NoisebrLocated in a peaceful residential neighborhood. Guests are asked to keep noise at a respectful level at all times, especially during evening hours. Violations may result in fines or termination of the reservation without refund.brbrPool depth ranges from 1 foot to 5 feet. Children will need to be supervised. There is no lifeguard on duty. Swim at your own risk.brbrWell-behaved pets are welcome with prior approval and a pet fee of $25 per day per pet. Pets must remain off furniture, be crated if left unattended, and are not permitted in the pool or hot tub. Additional cleaning or damage related to pets may result in added fees.brbrExtended StaysbrFor stays longer than two weeks, a required mid-stay cleaning is scheduled every two weeks to maintain the home to the highest standards. Optional linen and towel replacement is available upon request.brbrBooking guests must be at least 25 years old.brbrThis is a NON-SMOKING property. (Fine and cleaning fees apply if violated.)brbrAll guests that have a confirmed criminal record shall be declined and asked to cancel the booking at their own expense.brbrParking for up to 4 cars maximum. No street parking is allowed at any time.brbrSafety & Peace of MindbrThe home is equipped with fire extinguishers, smoke and gas detectors, pool depth markers, and decibel-based noise monitoring (no recording). Exterior security cameras monitor the front door, garage doors and home equipment for added peace of mind. NO cameras are inside the home or have a view of the inside of the house.brbrNo refunds will be given due to acts of nature unless there is a mandatory evacuation or prolonged outage of essential utilities.brbrWe have partnered with a Travel Insurance marketplace to offer you the opportunity for a little peace of mind through travel insurance that can potentially provide a full refund should life throw you some unexpected circumstances. Please inquire if you would like more information on travel insurance to insure your trip from unforeseeable events.brbrImportant Note:brbrThe guest gives permission to the property manager to use a third-party to screen my identity and check criminal databases to confirm my reservation. Complete terms regarding the guest screening can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions.brbrGuests enter the property via a keypad lock on the front door. We will provide an access code and check-in instructions before arrival.brbrMonthly or Longer stays require discounted house cleaning every 2 weeks paid by guest. Pets welcome. Pets need pre-approval. $25 per day per pet. Monthly discounts available. Pets are not allowed in the pool. Please keep pets off the furniture and crate your furry friends if you are planning on leaving them unattended.brAdditional rulesbr• Must upload Government ID upon Booking if not already completed.br• No Smoking anywhere inside the home or near the home openings. Smoking anywhere inside will result in a $500 remediation fee. Smoking is permitted on the front driveway or back yard away from house. Guest is responsible for cleaning up butts.br• Quiet Hours between 10 pm and 8 am. Sarasota has a noise ordinance program that is enforced by local law enforcement. We ask guests to please be considerate of neighbors and mindful of noise levels . We only recommend quiet guests to this home. Ignoring these noise ordinances can result in fines and termination of the rental agreement. .br• Check-in Any time After 4 PM. Check out 11 AM.br* We allow up to 4 cars parked on the driveway. You are not allowed to park on the street or you will get a ticket. Absolutely no RV or trailer parking on Driveway. No parking on lawn.br• If you have any needs or issues, you agree to message us through Airbnbbr• No parties, events, birthdays, bachelor or bachelorette stays - this includes `social gatherings` of any definition or reason.br• Do not have more guest than stated in your reservationbr• No Loud musicbr• There is 1 garage openers to use as a convenience. You will find it in the kitchen. Please return this openers to the kitchen. There is a $125.00 per remote if lost or not returned.br• We are not responsible or liable for any accidents, injuries or illness that occur while on the premises. We are not responsible for the loss of personal belongings or valuables during your stay. We cannot be responsible for any items left behind.br• There will be a minimum handling fee of $50, plus cost of shipping for anything you request being returned. Requests must be made with 7 days. Outside of 7 days, items may be donated at the sole discretion of the host.br• Mail service not supported. All packages will be rejected. We suggest guests that require mail delivery set up a temporary mailbox at the UPS Store or USPSbr• Security Deposit - any guest found to have damaged the home may be held liable and charged accordingly. Additionally, any guests found to have more people staying overnight at the property, or found having a party or event may be forced to forfeit the security deposit or may be asked to leave the premises. The authorities may also be contacted if necessary.br• 24-hour outdoor camera and remote security team monitoringbr• Noise detection sensors installed in and outside property – These devices monitor decibel levels at property 24 hours a day and automatically notify us if noise levels are too high. Surveillance or recording devices on property.

Luxury Retreat-Heated Pool-Hot Tub-Fire Pit-Minutes to Siesta Key Beach

Sarasota, Florida, United States

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Bath

Sleeps

$123.21

Welcome to Villa Siesta II !brbr MY name is KATYA . Hi! .We are NEWISH on VRBO but. not new to hosting,. We are super-hosts on airandBee where most of my reviews can be found - 2027 SPECIAL.. book 3 months or more and I will also pay for 2 monthly housekeepings (This only applies to the full season bookingbrIf I were you! I would Add Dec at shoulder season rates ). NOTE : JANUARY-APRIL 30 day minimum starting at beginning of month. Other months, we might be able to be more flexible.brbrYou will have your OWN LITTLE HOUSE, no noise all privacy and yet close to as much entertainment and golfing as you can tolerate lol. brIn my interaction with guests, I constantly hear, “this location has been awesome! “brThroughout half of 2024 and 2025: we have had private referrals staying herebrPET Yes w/ usual pet fee, but breed specific with dogs. non-shedding -OK LETS GO ! brVILLA SIESTA-moments to downtown, private, pristine, & very quiet. brOutside serenity, …..but excitement nearby! brTropical foliage, bromeliads, garden, , singing birds, wind, chimes, Large, pristine pool and.brbreakfast or happy hour in your private patio! brbr2 parking spacesbrbrThis is a well kept private safe community -a wide age range . There are very few villas in this area of Sarasota. usual condo style is more like apartments, with the buildings usually 2 levels or more .brYour neighbors are birds! brbr——————————————-brThis corner home's layout is open and classical…crown moldings, brbrLarge recent windows in every room reveal lush, landscaping adding wonderful dimensionality. brbrEnjoy morning, coffee or happy hours on private patio with mature foliage, brbromeliads -wind chimes - singing birds. brbrSliding glass doors from the kitchen make it easy to eat and entertain outside.brbrThe kitchen has granite countertops accented with mother of pearl and marble. -brrecent Stainless steel appliances & a quiet dishwasher. brRecent kitchen and bath lighting enhance already bright airy rooms.brFive Live tropical plants inside the unit will freshen your air.br*washer and dryer in unit, , br2 bathrooms, including unusual garden atrium, en suite master bath with walk-in shower. brbr3 smart TVs with Netflix & Amazonbrstreaming services (And cable TV available in the living room) living room is 50 inch TVbrbrCentral air conditioning and heat, electrical and Internet, all included.brbrKeyless entry -brpristine heated pool and cabana are just steps away...brbrThe primary bedroom with the en suite bathroom, has a newish queen size comfortable bed. Guest room has two single beds, (nu Image coming soon of new bedding]br & both have ample closet storage. brPhotographs will show each room & description.brbrkitchen is equipped all small appliances, dishes, bowls, and all conceivable size glasses, ... since I live in the same cul-de-sac anything you need ~I can hop right to it. Re housekeepingbrI can refer someone to you who knows the unit and won't break the bank!brbrI'm very hands-on, never intrusive.brbrPets Non shedding dog ok ($150 fee for any pet)brFull season rental, I’ll accept cats with interim cleaning....brBtw…no commercial trucks or vehicles with signage or motorcycles/boatsbrbrLETS OPEN A LITTLE CHAT…Tell me About yourself and and Some details … On this site (and on it’s major competitor) you can learn a lot about me. I need to know a little bit about you especially if you don’t have any references on this platform.. We don’t ever do instant booking. You might be surprised to learn that all I see is your name! We need to know it’s a good fit.brbrbrbr——TOURIST TROLLEY Free, nearby, takes you to beach and Saint Armand Circle etc.brings you tobr9/10 of a mile to the beginning of Main Street (the section of interest )brbrWalking distance to new Wawa and a number of necessity shops, such as Family Dollar, nail salon, and a new grocery store,, brvery close driving to downtown with lots of restaurants and movie, theater and play houses, ...brSarasota is known as the center of arts and culture ! brbrMy community sits in one of the best locations in Sarasota and people are migrating here from siesta key beach area !! Most people use cars /or electric bikes, or scooters and there is a bus route nearbybrbrSarasota is one of the most frequently mentioned tourist spots in the country but many people live here all year.. The airport is undergoing expansions to accommodate . It's 15 minutes driving to Villa Siesta from Sarasota airport.brbr————————-brbrIf you like.. I will start you out with breakfast fixings and then point you towards different types of stores. So you can inventory yourself. ..refrig has filtered water,brbrbut in season, we need you to brrent the ENTIRE month beginning on the FIRST. brFlexible off-season dates and rules are avail.brbrDISTANCESbrLIDO BEACH My favorite is 5.2 miles... get there in no time with a Scenic Drive... once there, you can walk to St Armands circle for lunch. Or a dozen happy hours and go bac k to beach !brbrSt Armands 4.6 miles brSarasota Airport 5.2 miles brMassages brLarsens on south Tuttle, trained Massage experts for $62 an hour -book ahead (This is not a commercial place like massage envy etc -it’s a chiropractor’s office)brbrRingling Circus Museum ( gotta see this) 5.3 miles brASOLO theater attached to the Ringling -plays and eventsbrThe famous Siesta Key Beach 8.5 mi Marietta Mus. of Art & Whimsy 5 mi brbrBayfront Marina with lots of boats excursions daytime and sunset br2 miles away free parking brbrMY FAVORITE: 2 miles away, a straight run... you are at the BayFront, I LOVE THIS BAYFRONT PARK, With OLeary' Tiki Bar frequently has music and it's free .......brbrTake a glass of wine and walk around this little Bayfront Park. Spectacular. Everytime I do it —I remember why I moved here LE BARGE party boat is right here as well two hour cruises in the bay of $45. Free Music - light food - bar menu. Walking distance - the same area is Marina Jacks restaurant a different level - atmosphere - price point valet parking available sometimes yachts pull up here and they dine. (SIGH). brDOWNTOWN Depending on your interest and ability, some of these places are walking distance. my 65 year old niece was here recently and walked to many downtown places on foot. Most people take cars in Florida Pretty much everywhere.brbrGOLF COURSES !! Pickleball-brbrREGAL cinema Moments away in downtown -br. recliner seating - inexpensive. free parkingbrCineBistro ..luxury movie theatre with dining, close by there is a downtown Burn’s court cinema that freq plays arty movies .brbrZILLIONS OF RESTAURANTS of every concievable cuisine brTheatrers, Opera House, Stand up comedy, improv, jazz, late night specials, Fogertyville has affordable music offerings in a cabaret type format with shared tables..you can choose seats online.. . FLORIDA STUDIO THEATRE has numerous types of offerings dinner theatre.. comedy.. plays..concerts. Attractive intimate settings and won’t break the bank..brbrromantic TOWLES court, artist community also in downtown, special events there...brMain Street area in downtown is hopping! lit trees, outdoor music / bars, - safe walking brbrBiking The famous Legacy Trail has been finished!brbrWalking distance is the LIME Street Apricot bazaar open Thurs -to Sat ,funky unique vendor mart, much of it handmade .. music, an outdoor eatery & socializing place.brAlso, an artist cooperative Gallery across the street from thatbrbrthe Bayfront is practically a straight run 2.4 miles from my door.br……..Famous Downtown Saturday morning POPULAR Market 1.8 miles brbrWhole Food Market, 1.6 miles. brJungle Gardens 4.4 miles brMarie Selby Botanical Gardens, .GORGEOUS 2.4 miles awaybrThe Bay.. outstanding park with performances ..many FREEbrSarasota Opera HOuse, Beatrice Friedman Symphony center, Players Theatre ..all shockingly close.brbrVan Wezel Performing Arts Hall ..outstanding venue with big namesbrMOTE Aquarium-has been finished .. newly opened late 2025 brBig Cat Habitat yes ! Art Shows.. endless shopping ..brSo many resale shops you won't believe.. brbrAnna Marie Island, LongBoat Key.. Ride a horse in the Gulf of Mexico brSail on a catamaran right out of the marina two miles away br Dolphins the manatees brbrWant some wild nature alligators More birds than I saw in Costa Rica bird wildlife.. Myackka River State Park, you'll think you are in Ecuador,..$6 car entrance ... 19 miles brbrIn Sarasota, there is kayaking, mangrove trails, all water sports, and every conceivable boat excursion.. dophins.. manatees.. Yipes I'm getting exhausted writing this.... brbrSUNSETS Sometimes there is a traffic jam going to the beach to see them!.brDrum Circle on Siesta Key beach Sun eve (During Covid I don’t know) Bird Key Park.. bring a beach chair, some benches available, great breeze, on the right before st ArmandsbrbrE-bikes Have arrived in Sarasota, and motorbikes, scooters, or regular bicycles.brbrYou can get to Venice..Ft Myers..Tampa or St Petersburg on superhighways, for example, the DALI MUSEUM..CHIHULY GLASS…THE IMAGINE MUSEUM brbut honestly..you might Not want to leave Sarasotabrbrthere's a free newspaper called the TICKET which is a MUST if you are interested in seeing a collection of clubs and music & theater & entertainment brbrClosish Walking distance is a new Wawa, great new discount grocery store, family dollar, dry cleaner, nail place, takeout Chinese food, pharmacy. Portuguese restaurant, 7-11, Pizza restaurantbrbrSarasota is on the international traveler’s map! COME and find out WHY!!

Villa

VILLA SIESTA-DOWNTOWN SECRET - HEATED POOL! NEAR BEACHES- GOLFING

Sarasota, Florida, United States

Bed