Vacation Rentals By Owner In Sarasota, FL

Showing 2800 Of 3494 Vacation Rentals

$520.82

Sun-filled garden villa corner 2Bd/2Bath unit

Sarasota, Florida, United States

Sun-filled end unit garden villa located just steps away from Siesta Keys award winning Crescent Beach. This home has a large master bedroom suite with king bed, double sinks in the bathroom vanity, a large stall shower, and a large cedar-lined walk-in closet. The second bedroom has a queen bed and a large walk-in closet. The hall bathroom has a shower/tub combo. The kitchen has state if the art stainless steel appliances and a new washer/dryer combo. Located in the garden section of the Gulf-front complex, contains larger, quieter condos, the view is of a lush tropical garden in a central courtyard. You may even walk out your sliding glass door onto the grass and find a Great White Egret (nicknamed Earl) waiting for you.

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$427.38

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Condo

Elegant Gulf view 2Bd/2Bath unit

Sarasota, Florida, United States

Elegant 1st floor, gulf view condo located just steps from the pool. You'll find everything you need to enjoy your beach vacation. The kitchen is bright and spacious it is fully equipped and has stone counter tops and stainless steel appliances. There is a king-size-bed in the main bedroom and the guest bedroom has two twin beds. Recently renovated, as well as various kitchen supplies. You will not be disappointed!

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Exceptional(3)

$191.28

/ Nightly

Condo

Cozy 2/2 Condo Meadows Wedgewood Lake

Sarasota, Florida, United States

Escape to this cozy 2-bedroom, 2-bathroom condo - perfectly situated in The Meadows Community which is just a short drive from Sarasota’s renowned Gulf beaches. Designed for comfort and relaxation, this inviting space is ideal for your next getaway. Sip your morning coffee in the Florida room or on the front patio, stroll along scenic trails teeming with wildlife, or unwind by the sparkling community pool.brbr** THE MEADOWS GOLF: Please note, golf course is projected to reopen November 2025. **brbrFeatures to Enhance Your Stay:brbr★ Patio:brRelax and soak in the Florida sunshine from the front patio, furnished with comfortable seating.brbr★ Living Room:brUnwind in the spacious living room featuring plush recliners, a three-seat sofa, and a TV with streaming and cable options - all offering a tranquil view of the lanai.brbr★ Dining Room:brEnjoy meals and conversation at the six-seat dining table, perfectly placed in the open floor plan for seamless interaction between guests.brbr★ Kitchen:brThe fully equipped kitchen includes a stove, oven, microwave, and dishwasher - plus a cozy breakfast nook with seating for two.brbr★ Bedrooms:brMaster Bedroom: A serene retreat with a queen-sized bed, walk-in closet, TV, and sliding doors to the lanai.brGuest Bedroom: Warm and welcoming, featuring two twin beds and a window with views of the front of the condo.brbr★ Bathrooms:brMaster Bath: Dual sinks, a walk-in shower, and toilet.brGuest Bath: A tub/shower combination, single sink, and toilet.brbr★ Laundry Room:brStay refreshed with the convenience of an in-unit washer and dryer.brbrPrime Location:brEnjoy proximity to shopping, dining, and entertainment at the UTC Mall, quick access to I-75, and to nearby attractions like Nathan Benderson Park. brVenture to Sarasota’s vibrant downtown, or relax on the white sands of Siesta Key or Lido Key - all within a short drive.brbrThe Meadows Community:brThe Meadows offers a peaceful, nature-inspired retreat with extensive trails for walking, biking, and bird watching. brOptional seasonal memberships to The Meadows Country Club provide access to an 18-hole golf course, tennis courts, lap pool, dining, and social activities ( separate fees apply). Please note that pool temperature may vary depending on outdoor conditions, and during colder weather, it may not always reach the desired setting. The pool is heated seasonally in accordance with Homeowners Association guidelines. Guests are kindly asked to follow all HOA pool rules, including posted hours of operation.brbr★ High Season Booking Policy (January 1 – March 31)brThis rental is available by calendar month only, with check-in on the 1st of the month. Guests may book 1, 2, or more consecutive calendar months. Thank you for your understanding!brbrImportant Information:brHOA Application: Required for rentals, submitted 30 days before arrival, with a $100 fee included in your booking (subject to change).brCommunity Rules: No pets, parties, or smoking allowed. brOvernight parking restrictions apply for pick-up trucks, commercial vehicles, and motorcycles.brProperty Guidelines: Maintain AC at 70°F or above, heat at 77°F or below, and keep windows/doors closed when running HVAC.brFor your safety, swimming is at your own risk, and children must be supervised at all times.brTraveling with friends or family Check out additional managed units within The Meadows for group accommodations.brbr★Add-on:brTraveling with a little one We offer a Pack 'n Play for use during your stay for a one-time fee of $50. This includes clean, fitted sheets for your convenience. Just let us know in advance if you'd like to add this to your booking!brbrWildlife Awareness:brRespect Florida’s diverse wildlife. Avoid direct contact and follow safety guidelines. For more information, visit the Florida Fish and Wildlife Conservation Commission website.brbrYour serene coastal getaway awaits—book today and start making memories!

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$427.38

/ Nightly

Condo

Enjoy beautiful sunset views

Sarasota, Florida, United States

Enjoy your stay in this second floor gulf view unit with a beach theme throughout the condo! Bright white fully equipped kitchen. The main bedroom has a king-sized bed, the guest bedroom has 2 double beds and there is a pullout sofa bed located in the living room. this unit will accommodate 6 people easily. Enjoy sunset views from you screened in lanai. You will never want to leave this beach paradise!

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$427.38

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Coastal chic 2 Bed/ 2bath Condo

Sarasota, Florida, United States

Spacious 2 bedroom, 2 bath, 2nd floor renovated unit on #1 ranked Siesta Beach. Fantastic gulf, beach and pool views from the living room, lanai and master bedroom allow you to leave your cares behind. Both bedroom furniture's have been updated spring 2023. The bathrooms have been updated with elevated toilets and shower seats. The guest bath has multiple grab bars and a detachable shower wand. The living room features a HD 65 Smart TV.

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$427.38

/ Nightly

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Lovely Beach front 2Bd/2Bath Condo

Sarasota, Florida, United States

Our condominium is in Building 5 Unit 203 and is located beachfront at the Siesta Dunes Resort on Crescent Beach, about a half mile north of Stickney Point Road on Midnight Pass Road. We are on the second floor with a beautiful view, taking in the poll area, landscaped grounds, and the beach. Some of the unique features are the sun deck right next to the beach with a grilling area, plenty of lounge chairs, and a shaded area. The pool is spacious, surrounded by beach chairs, and a natural sea grass landscape theme. There is an elevator and laundry facility ten steps down the hall from our unit. We treat our condominium as home, not strictly a rental or business venture. Furnishings are high quality as are the appliances and electronics. Everything you need for a perfect vacation is provided. Linen, china, flatware, modern updated appliances, coffee maker, toaster, etc. We've constantly updated, painted, modernized, all in good taste, all high quality. This unit is suitable for adults only.

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$569.07

/ Nightly

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Crescent Beach Gulf view 2 Bed/2Bath Condo

Sarasota, Florida, United States

Escape to paradise in this beautifully updated 2-bedroom, 2-bath first-floor condo located in the heart of Siesta Key. With direct walk-out access to both the beach and the pool, this coastal retreat offers the perfect blend of convenience, comfort, and island luxury. Step inside to find a bright and modern interior featuring an open floor plan, a fully equipped kitchen with updated appliances, and stylish finishes throughout. Both bedrooms are spacious and serene, with ample closet space and updated bathrooms for your comfort. Start your mornings with coffee on the patio just steps from the sand, and spend your days soaking up the Florida sun by the pool or on the world-famous Siesta Key Beach—just outside your door.

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$427.38

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Cozy Gulfview 2Bed/2Bath Condo

Sarasota, Florida, United States

Nice comfortable ground floor unit with tile throughout the condo. Recently remodeled with neutral decor. The kitchen is fully equipped, has stone counter tops and all stainless steel appliances with a Keurig and a wine cooler! The living room has a 55 inch HDTV and wireless internet access. This unit has a screened in lanai and outside patio area. The main bedroom has a king sized bed and the guest bedroom has two twin beds. Steps to pool and short walk to beach.

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$427.38

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Condo

Ground Floor Gulfview 2 bed/2bath condo

Sarasota, Florida, United States

Enjoy this newly renovated ground floor gulf-view unit, just steps to the pool and a short walk past the sun deck to the white sandy beach. This unit comfortably sleeps six: the master bedroom has a king bed, the guest bedroom has a twin bed and a full bed, and the living room has a sectional sleeper sofa. The kitchen is fully equipped, and both the master bedroom and guest bedroom closets have custom closet systems. This unit has an outside patio area off the master bedroom and a screened-in lanai off the living room. All of the comforts of home for your Siesta Key vacation. *Kitchen and lanai to be remodeled early Summer 2026.*

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$427.38

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Condo

Crescent Beach Contemporary 2bd/2Ba Condo

Sarasota, Florida, United States

This ground floor, 2 bedroom, 2 bathroom pool/gulf view is beautifully updated. The kitchen is fully equipped and has all stainless steel appliances. This unit has lots of natural light coming through. The main bedroom has a King size bed and the guest bedroom has 1 full size and 1 twin bed. Easy access to the pool and the beach through the gulf side sliding doors. The unit comfortable sleeps 6 and also has a washer/dryer which is rare for this building!

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$395.15

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Tropical garden view 2 Bed /2 Ba

Sarasota, Florida, United States

Enjoy a lush tropical garden from your screened in lanai. Located on the ground floor with convenient parking just outside. This two bedroom two bath unit sleeps 4. The main bedroom has a king-sized bed and the guest bedroom has 2 twin beds with old Florida ceiling fans in the bedrooms. The unit has a fully equipped kitchen with stainless steel appliances Quiet Florida living with all the amenities.

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Exceptional(56)

$167.24

/ Nightly

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Lido Beach Gulf View Condo w/ pool. Right across from beach! ! OFF SEASON RATES

Sarasota, Florida, United States

Panoramic ocean View . 1bd, 1bth located immediately across for the beach. Right in the middle of Lido Beach. Close to St. Armands Circle with shopping, restaurants, entertainment, music. King size bed in the master bedroom and newer sleeper sofa with easily accomodate 2 more people in the living room. Fully equipped unit, Linens, all towels, beach towels, blender, toster, coffee maker, eveything you need for cooking. 2TVs, a DVD player, cable, wireless internet. Laundry facilities. beach chairs.brWalk to the St. Armand Circle where there is plenty of restaurants, shopping and entertainments. br br br br br

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Exceptional(62)

$285.49

/ Nightly

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Walk to Lido Beach, Walk to Armand Cir with Dining & Shopping, WiFi, Xfinity, 2TV's, Heated Pool/Spa

Sarasota, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Kingston Arms 1st Floor! brbr brbrSimply paradise! This coveted end unit in Kingston Arms on Lido Key is just steps from St. Armand’s Circle and a few blocks from the pristine white sands of Lido Beach. Enjoy upscale shopping, dining, and nightly entertainment nearby, while still having a peaceful retreat surrounded by the clear, gentle waters of the Gulf of Mexico. brbr brbrLOCATION HIGHLIGHTS: brbr- Walk to St. Armand’s Circle for high-end shopping, upscale dining, and nightly live entertainment brbr- Just a few minutes walk to North Lido Beach & Park brbr- Heated communal pool, brbr- Just west of Downtown Sarasota across the Ringling Bridge brbr- Easy access to beaches, restaurants, nightlife, and nearby Longboat Key brbr brbrPROPERTY FEATURES: brbr- 2 Bedroom/ 2 bathroom ground floor condo brbr- Private screened lanai brbr- Communal laundry room (no private laundry) brbr- Assigned covered parking for one car brbr- Towels and linens provided brbr- Keyless entry, self check in brbr brbrLIVING ROOM: brbr- Spacious living area with sofa for 3, love seat for 2, upholstered lounge chair brbr- Big flat screen TV with Xfinity cable and WiFi brbr- Natural light from floor to ceiling sliders brbr- Access to screened lanai, right across from the pool brbr brbrKITCHEN AND DINING: brbr- Modern kitchen with solid stone counters and stainless steel appliances brbr- Ample cabinet space stocked with pots, pans, and meal prep essentials brbr- Dining table seats 6 comfortably brbr brbrBEDROOMS AND BATHROOMS: brbr- Master Bedroom: King bed with memory foam mattress, ensuite bath, large closet, dresser, TV with cable brbr- Guest Bedroom: Two twin beds with memory foam mattresses, large closet, tall dresser, work desk, plank tile floors brbr- Master ensuite bathroom: custom tiled step-in shower, grab bar, adjustable dual shower head, granite counter brbr- Second Bathroom: Remodeled with newly tiled step-in shower, grab bar, adjustable shower head brbr brbrEXTRA PERKS: brbr- Complimentary beach items: a couple of beach chairs, a beach umbrella, and beach towels brbr brbrLOCAL FAVORITES: brbr- St Armand's: Columbia, Daquiri Deck, Crab and Fin, Cha Cha Coconuts brbr- Shopping: Alvin's Island, Beach Bazaar, Foxy Lady brbr brbrIMPORTANT INFO: brbr- No pets, no smoking or vaping inside or near windows/doors brbr- Parking restrictions for special vehicles: boats, motorcycles, trailers, jet skis, kayaks, golf carts, monster trucks; confirm prior to booking brbr brbrRELAX, REJUVENATE AND RECHARGE. YOU WILL NOT WANT TO LEAVE!brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

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Exceptional(8)

$337.87

/ Nightly

Condo

Near Siesta Key. Lg Patio. 2 King beds, Wi-Fi, Updated Sarasota Condo. 1st floor

Sarasota, Florida, United States

Ground floor updated 2 Br condo with newer 24 porcelain tile, new kitchen cabinets, granite countertops, appliances, and most furniture and furnishings. brbr2 bedrooms with a king bed in each bedroom, full kitchen, dining area, and large covered patio. The living room has a large TV, sofa, chair, and a futon that folds into an additional bed. 8' wide sliding glass patio doors lead out to your 28' long private lanai (covered patio) from the living room and master bedroom. br brWe are within 2 miles of Siesta Key. We are just up the road from the bridge for an easy commute. Siesta Key has stunning white sand beaches, restaurants, shops, and live music. Downtown Sarasota is about 3 miles. We are within walking distance of several restaurants, shops, and groceries. This is a convenient easy location to get out and about to the many things Sarasota has to offer.br brFree Wi-FI and a designated parking space. Additional parking may be available for a fee. Inquire if needed. The washer and dryer are located in a shared coin-operated laundry room on the ground floor.brbrMaximum condo occupancy is 6 including all children. Correct occupancy must be in the reservation or communicated & paid before check-in. brNo Smoking. We are a smoke-free property indoors and outdoors.brNo pets. Let me know if you have any questions.

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Exceptional(2)

$119.45

/ Nightly

Condo

Beautiful golf course view from this condo

Sarasota, Florida, United States

Vacation RentalbrbrCondo Association Approval Required. Application Will be sent after property is booked.brbrWelcome to the Meadows Country Club! Nestled in the heart of Sarasota, Florida, this ground floor condo offers a fantastic opportunity for a comfortable and convenient rental experience. With a stunning view of the lush golf course, this 2 bedroom, 2 bathroom condo is perfect for those seeking a serene and relaxing lifestyle. As you enter the condo, you'll be greeted by a tastefully decorated living space that exudes warmth and style. The cozy living room features ample seating and a large flat-screen TV, perfect for movie nights or watching your favorite sports games. The adjacent dining area offers a lovely space to enjoy meals with family and friends. The well-equipped kitchen boasts modern appliances, including a dishwasher, oven, and microwave, making meal preparation a breeze. Enjoy your morning coffee or evening cocktails on the screened lanai, overlooking the golf course, and soak in the tranquil ambiance. The master bedroom features a comfortable queen-sized bed, perfect for a good night's sleep after a day of golfing or exploring the nearby attractions. The en-suite bathroom offers a walk-in shower and all the amenities you need for your stay. The guest room features two twin-sized beds, perfect for accommodating additional guests or setting up a home office. The second bathroom includes a bathtub/shower combination and is conveniently located adjacent to the guest room. This condo is located within minutes of the popular UTC shopping area, offering a wide variety of shops, restaurants, and entertainment options. Siesta Key Beach, known for its pristine white sand and turquoise waters, is also just a short drive away, making it easy to enjoy beach outings and water activities. Additional amenities of this rental property include access to the community pool, tennis courts, and golf course (for an additional fee), as well as a washer and dryer in the unit for added convenience. Don't miss this opportunity to experience the best of Florida living in this beautifully decorated condo with golf course views, convenient location, and all the comforts of home. Book your stay now and create unforgettable memories in the Meadows Country Club!

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$427.38

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Condo

Watch the sunset from you screened in lanai in this 2bd/2ba Condo

Sarasota, Florida, United States

Enjoy the beautiful view from your screened in lanai. This Recently Renovated 2 Bedroom, 2 Bathroom unit is located on the ground floor. The condo is a gulf view unit. The kitchen is fully equipped. It comfortably sleeps 6 people with 2 queen beds in the guest bedroom and 1 king size bed in the main bedroom. The condo is conveniently located near the pool with walk out access through the living area.

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$392.92

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Condo

Crescent Beach Gulf view 2Bd/2Ba Condo

Sarasota, Florida, United States

Siesta Dunes Beachfront Condominiums offers our special guests a selection of over 100 Siesta Key vacation condo rentals located on the beach at 6200 Midnight Pass Road, Siesta Key, Florida 34242. Our beautiful sandy beaches of Siesta Key along the Florida Gulf Coast are right out your door, and you'll also enjoy the pool and hot tub, beach deck and pavilion, tennis courts, club house, and plenty of restaurants and entertainment along Midnight Pass Road. Call us today and rent a condo on the world's best beaches. Our friendly staff looks forward to meeting you and can be reached at (941) 346-0210 or by email at info@SiestaDunes.com

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$183.2

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Private Vacation Home

Private Heated Pool Casita Near Downtown & Beaches in Pinecraft.

Sarasota, Florida, United States

Built in 1925, Our Casita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures. brbrThe Kitchen is open with Granite Counters and everything is included to make your stay comfortable. Even a Krups Coffee Maker for your morning Cup O’ Joe.brbrEnjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Up to 2 medium sized dogs. We hope you will make our Casita Verde a permanent part of your Sarasota vacation.brbrCert # VR24-00152

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$935.59

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Private Vacation Home

5 Star Rated Estate on the water Heated Pool plenty of privacy almost 2 acres

Sarasota, Florida, United States

Experience Sarasota like a local in this 5-bedroom estate. The space features 4 bathrooms and a cozy living room with a murphy bed and sofa bed, perfect for extra guests. Inside, you’ll find a king bed, three queen beds, a crib, and a bunk bed, making it ideal for families or groups. The estate offers a welcoming atmosphere where guests can relax and unwind. Whether you’re gathering in the spacious living areas or enjoying some quiet time, this adorable home provides an enjoyable retreat. Make your holiday one for the books with a stay at our place.

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Exceptional(11)

$238.3

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Condo

Book Me Baby! Esquina Paraiso on Siesta Key

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You To Esquina Paraiso!brKing / Queen / Fullbr“A Little Corner of Paradise!”brbrPinkie Flamingo had actually taken 6 years of Spanish along the way, which had proven very helpful. As a curator of fine vacation rentals along Florida's Gulf coast, it was Pinkie's job to find the very best guest nests and make them available to her flock of friends & travelers. “¡Qué lugar de vacaciones tan fabuloso!” Pinkie exclaimed. From her vantage point well above the tree line, Pinkie Flamingo had a spectacular “bird's eye view” of the entire lay of the land. Stretching her wings luxuriously, she floated over private homes and resorts…each standing ready to welcome those fortuitous enough to have discovered the long-standing charm of Siesta Key.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! Consistently ranked The #1 Beach in America, Siesta Key achieves its lofty position in the beach rankings among some fierce competition. While no beach can ever be considered a bad beach…(I mean it's a beach right ) 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.brbrLet's Find Out More About Esquina Paraiso!brbr2 Bedroom / 2 bath 5th floor unit with sweeping coastal viewsbrSunny corner condo with 3 balconiesbrOutdoor seating & diningbrGorgeous views of the Intercoastal Waterway and the GulfbrCozy living space featuring beach decor in soothing beige & blue palettebrBeach gear included…beach cart / 4 chairs / umbrella / beach towelsbrPrimo resort location at The Anchorage near south bridgebrPrivate beach access right across the streetbrSeasonally-heated Olympic size swimming poolbrLighted tennis courtsbrFitness centerbrClub roombrPicnic area by IntercoastalbrGrillsbrShuffleboardbrBasketballbrCorn HolebrBoat dockingbrbrWorld-class favorites Siesta Key, Longboat Key and Anna Maria Island head the line-up of this all star cast along the 35-mile stretch of pristine beaches to the west of Sarasota. With an undeniable sophistication and long-standing international appeal, the area has rightfully earned the nickname the Culture Coast. From the classy vibe surrounding St. Armand's Circle to the laid-back beachy charm of Anna Maria Island, there is something for everybody. The area's cultural heritage was defined in large part by philanthropist John Ringling. As a renowned patron of the arts and co-founder of the Ringling Bros Circus, his contributions in art and architecture set the stage for the area to flourish as a tourism hotspot for concerts, theater, festivals, award-winning dining, outdoor sports, aquatics, shopping and much more!brbrCome To Florida…For The Fun of it!brbrAll of Pinkie's Properties Have A Few Things In CommonbrMust Be 25 To BookbrNo SmokingbrCancellation OK 30 Days Prior To Check-InbrSheets & Bath Towels Included…BYO Beach TowelsbrAll Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & FoodbrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending obrBasic Essentials Starter Set Only…TP, Paper Towels, Trash Bags, Soaps, Etc …Depending on Length of Stay You May Need More

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Vacation Rentals By Owner In Sarasota, FL

$520.82

$427.38

$191.28

$427.38

$427.38

$427.38

$569.07

$427.38

$427.38

$427.38

$395.15

$167.24

$285.49

$337.87

$119.45

$427.38

$392.92

$183.2

$935.59

$238.3

Rent a place that suits your needs

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