Home Vacation Condo Rentals By Owner In Sarasota, FL

Showing 960 Of 1190 Vacation Rentals
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Exceptional(56)

$227.89

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Discounted rates for gorgeous one bdrm directly across from beach, near village!

Sarasota, Florida, United States

Due to a cancellation we now have July 4-10 available- see the magnificent fireworks on Siesta beach by just walking across the street! We currently are offering a minimum 4 night booking policy during June 6 to December 11. (After that date, until mid-April, the minimum night stay will go to 7 nights and require Saturday to Saturday bookings.) In addition, as of now we still have some weeks available next January, February and March - however they won’t last very long! Gorgeous updated, just renovated, newly furnished one bedroom! Best location on Siesta beach and a short walk to charming Siesta village! Enjoy a perfect Florida vacation at our Condo (unit 109) - directly across from world-famous Siesta Beach (Rated the #1 beach in the US)! brbrOur especially well maintained, upscale one bedroom, one bath condo is in the condominium complex closest to Siesta Beach -- known for having the whitest sand in the world (with the look and feel of baby powder). We are only one mile from Siesta Village, with its excellent shops and restaurants! Our guests are usually couples or two persons, although we will allow three people. brbrA free trolley takes you from our condo complex to Siesta Village!brbrWalk out of our convenient first-floor unit's lanai, go sixty steps - and you're on this magnificent, breathtaking beach. Our condo is decorated in a coastal chic beach house theme. Our screened in lanai is perfect for eating your breakfast outside or watching amazing sunsets - perhaps with a glass of wine. A super comfy new King size bed awaits you in the bedroom. If a third person occupies the unit we have a pullout queen size bed. There are two cable TVs and in addition, of course, we have WiFi internet access. The beautiful, oversized swimming pool is heated when necessary, and a clubhouse provides a fitness room, library, a pool table and table tennis. Several bar-be-que grills are available. br brWe're located in the best area of Siesta Key, an upscale resort island just over the bridge from Sarasota. Whether you stick to Siesta Key or go into Sarasota itself, you'll find every type of resort activity available and a choice of hundreds of fabulous restaurants. And now -- there is a brand new casual restaurant -- the only one on the beach with stunning Gulf views -- right across from our condo! brbrBest of all, we've made our rates the most reasonable offered anywhere on the Key! Although most of our guests have access to a car -- now that there is the free trolley to Siesta Village -- some visitors may opt to get away without a car rental. Most of our guests love our condo, write fabulous reviews— and return each year! Be sure to read them! Saturday December 26, 2026 checkout required for Christmas week. Saturday check in and departure required during mid-December to mid- April. Renters must be at least 25 years old! The condominium association absolutely forbids pets in the units!
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$227.97

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Siesta Key 2BR | Walk to Beach | Private Entry

Sarasota, Florida, United States

Experience the best of Siesta Key living in this beautifully furnished first-floor condo located within the highly desirable Harbor Towers community. With a private entrance and no elevators or lobby access to navigate, this condo offers seamless convenience from the moment you arrive.brbrEnjoy your morning coffee or outdoor dining on the private patio, with assigned parking just steps away for easy access when unloading groceries, beach gear, or returning from a day on Siesta Key Beach.brbrInside, the condo features light coastal-inspired furnishings, beach-themed décor, and a comfortable, inviting atmosphere designed for both short getaways and extended stays. The modern kitchen includes updated appliances and everything needed for easy meal preparation, and beach chairs are provided for added convenience.brbrHarbor Towers Resort-Style Amenities Include:brbr• Heated poolbr• Clay tennis courtsbr• BBQ grilling areabr• Fitness centerbr• Sauna, showers, and locker areasbr• Clubhouse with pool table, TV, refrigerator, ice machine, and gathering spacebr• Waterfront gazebo ideal for sunset views, dolphin sightings, and manatee watchingbrbrOne of the best features of Harbor Towers is the free trolley stop located directly in front of the building, providing easy access to Siesta Key Beach and Siesta Key Village for dining, shopping, and entertainment without the hassle of parking.brbrThe condo is approximately a 10-minute walk to Siesta Key’s famous white sand beach and only a quick 2-minute trolley ride to the beach access points and Village area.brbrWhether you're visiting for a relaxing beach escape, seasonal stay, or extended coastal retreat, this condo offers the perfect combination of comfort, convenience, and full access to one of Siesta Key’s most sought-after communities.
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Exceptional(2)

$478.78

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Crescent Arms Vacation Rentals 501S Siesta Key Florida

Sarasota, Florida, United States

Crescent Arms unit CA 501S Welcome to Barbs Siesta Beach Getaway. This unit is new to the Crescent Arms Rental program and has opening during the prime rental season. These openings will not last long. Book your favorite time to vacation quickly before all the openings are taken! It is a highly coveted front center unit. Featuring the best views of the white sandy beach and the vast sunsets that Siesta key has to offer. This unit has a huge Lanai that is accessible from the living area and both bedrooms through sliding glass doors. The 2 bedrooms are separated by the living room offering privacy in each bedroom with their own bathroom en suite. Every room has a view of the water while cooking dinner at night to relaxing in your bed in the morning you can watch the seagulls fly by and hear the waves lapping against the white sand beach. Barb has the unit decorated is a tasteful costal beach decor. The decor brings the beautiful beach view into the unit while staying sleek and clean feeling. This unit is perfect for your romantic getaway or for a small family.brThis unit Features:brBeach front property! Easy access on and off the Island! No loading up a car or crossing streets just walk out of the building onto the sand! 2 Bedroom 2 bathroom. Sleeps up to 4 people. The Main bedroom has a queen bed with private bathroom the Guest room has 2 twin beds and a private bathroom. Screened in lanai with patio furniture. Full kitchen, dining area, Tv in each room with free Wi-Fi. brShared resort amenities:brHeated pool, Private Beach, BBQ area with gas grills. Beach chairs provided. Beach personnel you can rent an umbrella from. Beach towels included. Bed linens and bath towels included. We do not have a linen service if you would like fresh linen you will have to wash them. Coin operated laundry in the tower buildings. Villas have washers and dryers in the garage No smoking and no pets, please! NO GOLF CARTS, Trailers, motorcycles, mopeds, boats If you want to enjoy the sugar-white sand of Crescent Beach, shop or just relax by the pool, located directly on the beach side of Midnight Pass Road, we offer something for everyone: Wi-Fi, cable television, generous closet space, a lanai or glassed-in porch and a fully furnished kitchen. Crescent Arms features: Fully Furnished, Gated Condominiums Private Beach Access with Chairs No smoking and no pets, please!brThere is a seven-night minimum stay Saturday to Saturday. Check in: 4 PM Check out: 10 AM. We strongly encourage you to get rental insurance in case of any problems that may occur. Your Florida Vacation Awaits You.
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Exceptional(17)

$441.5

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Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!

Sarasota, Florida, United States

Completely Renovated includes 2 New AC/Heat units. All new Luxury and Comfort! Beach Cottage on World Famous Siesta Key Beach in the heart of it all. Park Free-next to unit, no steps. Walk everywhere! Great Dining, entertainment, shopping, bike rentals and more, across the street or take FreeTrolley to Siesta Key Village. Located on the Beach Side (3-5 min.walk to waters edge) with Heated Pool and private Gate Entries. Best Location on the Island! Private large outdoor Patio w/outdoor shower. Includes Beach Buggy with Beach Equipment and Chairs. Beach Towels and Luxury Oversized Bath Towels. In Unit Washer/Dryer. Free Luxury Amenities such as Egyptian Cotton Sheets, additional bed pillows, HypoAllergenic Bedding and Pillows, Blackout Curtains in the bedroom, Coconut Bath Products. I even include coffee, cream and sugar! Highly sought after 1 bd 1ba with living room, full kitchen and 2 Smart TV's with YouTubeTV. Book your stay in advance! I've been coming here since the 70's and I can help you plan your perfect Getaway! All 5 star reviews as a Premier Host. This is the largest unit in the complex. I love this place and you will too. I'm known for repeat guests in my units. This one is even better! I provide books and games, dining room table inside and outside, as well as a study table and additional charging station for your phones on the back of both nightstands. The private outdoor patio has dining table, umbrella and chairs as well as outdoor lights at night on auto timers. Even has an outdoor shower for your use. The new appliances and the kitchen is fully stocked with everything you need to stay for a month, even wine and champagne glasses. I give all my guests my restaurant recommendations and locations. I offer discounts for boat tours thru my friend Captain Cory, info provided in the unit. Everything you need for a great time! Enjoy! I look forward to hosting you. Phyllis
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Exceptional(39)

$189.96

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Pineapple Cove: Ground-Floor Comfort; Short Walk to Beach, Dining & Shops!

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 Pineapple Cove! brbr brbrExperience the best of Siesta Key at Pineapple Cove, a beautifully updated one-bedroom retreat on the vibrant south end of the island. Whether you’re here for a week of sun-drenched relaxation, a solo coastal getaway, or a small family beach break, this ground-floor condo puts you right where you want to be. brbr brbrLOCATION HIGHLIGHTS brbrSkip the parking hassle! You are perfectly positioned for a car-free vacation: brbr- Beach Access: A breezy 6-minute stroll to Crescent Beach (Access #12 & #13). brbr- Nature’s Beauty: 7 minutes to the famous Point of Rocks for snorkeling and scenery. brbr- Island Life: Walkable to local favorites like Captain Curt’s, Big Water Fish Market, and the Orange Octopus for dessert - just a few minutes from your doorstep! brbr- Easy Transport: Hop on the free Siesta Key Breeze Trolley nearby for a stress-free ride to Siesta Village for more shopping and dining. brbr brbrTHE SPACE brbr- Living: Open, beach-themed living area featuring a queen sleeper sofa and a screened lanai. The perfect spot for morning coffee in the salt air. brbr- Rest: A serene Master Suite with a cooling queen mattress and wall-mounted Roku TV. brbr- Kitchen: Fully equipped for beachside brunch or a quiet dinner at home, with dining seating for four. brbr- Perks: Dedicated High-Speed WiFi, beach chairs, umbrella, and towels are all provided. brbr brbrAT A GLANCE: brbr- Sleeps: Up to 4 guests. brbr- Convenience: Ground floor unit, bike rack, and communal laundry. brbr- No smoking/vaping brbr- No pets brbr- Self check in with keyless lock brbr brbrDiscover your perfect Siesta Key rhythm. Book your stay at Pineapple Cove today!brbrWe help make the most of your vacation by providing Xplorie's Free Admission to some of the area’s top attractions each and every day including a choice of a free bike rental, kayak rental, a dolphin cruise tour, or admission to the Ringling Museum ! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA with advance reservation. The fare is free but please tip the driver. Limited to one activity for just one person each day (other members of the group can partake but will need to pay). Create exciting memories, have more fun, and truly experience the Beaches of Sarasota! Book now for an amazing vacation experience! Activities are subject to change and based on availability; non-cumulative and non-transferrable.brbrbrbrimg src=https://admin.itrip.net/upload/360/marketingimageitripsarasota.1718820503.jpg alt=marketing /brbrbrbrFeel free to book for a month or longer but Xplorie is not available for booking 25 days or longer.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(1)

$196.08

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Perfect Monthly Rental | Updated 3-Bedroom Condo | Heated Pools | Short Drive to Beaches

Sarasota, Florida, United States

Welcome to your Sarasota getaway! brbr brbrNestled in the heart of the vibrant Village Brooke community, this beautifully remodeled 3-bedroom, 2-bath condo is perfect for extended stays, offering modern comforts and unbeatable amenities. Whether you're here to relax by the pool, explore Sarasota's world-class attractions, or simply escape to a home away from home, this is your ideal retreat. brbr brbrLOCATION HIGHLIGHTS: brbr- Village Brooke community in central Sarasota brbr- Minutes to Siesta Key Beach, shopping, dining & golf brbr- Less than 1 mile to Publix & Starbucks brbr- Easy access to local attractions, boating, and outdoor recreation brbr brbrPROPERTY FEATURES: brbr- 3 bedroom/ 2 bathroom 2nd floor condo (1144 sq ft) brbr- Fully remodeled condo, modern finishes throughout brbr- 2 heated community pools, tennis courts & shuffleboard brbr- Clubhouse with kitchen and lounge space brbr- Assigned parking space brbr- Upstairs unit (stair access only) brbr- Dedicated WIFI, central AC brbr- Community laundry – app-operated (no coins needed) brbr brbrLIVING ROOM: brbr- Comfortable living area with Smart TV + cable brbr- Streaming-ready entertainment setup brbr- Private balcony for morning coffee or evening relaxation brbr brbrKITCHEN & DINING: brbr- Updated kitchen with stainless appliances brbr- Granite countertops & fully stocked essentials brbr- Dining table seats 6 plus 4 at kitchen island brbr brbrBEDROOMS & BATHROOMS: brbr- Master suite – NEW hybrid king mattress + en-suite bath with walk in shower brbr- 2nd & 3rd bedrooms – Queen beds & ample closets brbr- Guest bathroom with updated vanity and tub/shower combo brbr brbrEXTRA PERKS: brbr- Close to golf courses, beaches & local cafés brbr- Ideal for extended stays or work-from-anywhere stays brbr brbrIMPORTANT INFO: brbr- HOA application & approval required – allow minimum 10 days for approval brbr- Minimum stay required (varies by season) brbr- No pets, smoking or vaping permitted brbr- Parking restrictions: no boats, pick-up trucks, motorcycle, trailers, jet skis, or any oversized or commercial vehicles allowed. brbr brbrBOOK YOUR SARASOTA STAY AT VILLAGE BROOKE AND EXPERIENCE THE PERFECT BALANCE OF RELAXATION AND CONVENIENCE.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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$117.87

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STUNNING 2 BED 2 BATH CONDO IN STONEYBROOK GOLF AND COUNTRY CLUB

Sarasota, Florida, United States

Escape to paradise in this beautifully appointed ground-floor condo located in the prestigious STONEYBROOK GOLF AND COUNTRY CLUB. Overlooking the lush 17th green, this 2-bedroom, 2-bathroom retreat offers all the comforts of home with resort-style amenities just steps away.brbrPROPERTY HIGHLIGHTS:brGround-floor convenience — no stairs, easy access, and your own one-car garagebrStunning golf course views from the furnished rear patiobrNewer furnishings, ceiling fans, blinds, and window treatments throughoutbrCentral heat and air conditioning for year-round comfortbrElectric, cable, and Wi-Fi includedbrTwo flat-screen TVs, one in the living room and one in the main bedroombrWasher and dryer in unitbrBeach towels, pool float, and noodles provided for your leisurebrThe community pool is located directly across the street, making it effortless to enjoy a swim or relax in the sun.brbrFULLY EQUIPPED KITCHEN:brCook your favorite meals with ease in a kitchen that offers:brNewer electric range (2022)brFull set of appliances, cookware, dishes, glasses, utensilsbrBlender, coffeemaker, and all the essentials you need for a comfortable stay.brbrBEDROOMS AND BATHROOMS:brPrimary Suite:brKing-size bed with fresh linens and pillowsbrUpdated ensuite bathroom featuring dual sinks and walk-in showerbrTowels, bathrobes, and slippers includedbrSecond Bedroom:brQueen-size bed with quality linensbrAccess to an updated guest bath with a tub/shower combobrTowels, bathrobe, and slippers provided.brbrRESORT AMENITIES:brEnjoy access to the Stoneybrook Clubhouse, which features:brOn-site dining and barbrFitness center and poolbrPro Shop and optional golf privileges (transferable membership available for a separate fee depending on stay length)brbrADDITIONAL DETAILS:brMinimum stay: 30 daysbrNo petsbrNo smokingbrMinimum age requirement: 25brbrPerfect for a seasonal getaway or extended stay, this elegant condo offers the ideal combination of peace, privacy, and proximity to Florida’s best beaches, shops, and restaurants.brbrWake up to a peaceful view, sip your coffee on the patio, and experience the relaxed luxury of Stoneybrook living — home away from home.
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Exceptional(41)

$279.13

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St. Armands Circle Sarasota, Florida - Restaurants, Shopping, Beaches, Sun & Fun

Sarasota, Florida, United States

An updated two bedroom, two bath condo near St . Armand’s Circle, with all of the excitement of various restaurant's and many boutique shops within easy walking distance of your condo. Within the complex of Kingston Arms, you wouldn't know the circle even existed. Sitting at the pool in the courtyard of swaying palms, swimming, enjoying the hot tub or enjoying a refreshing beverage sharing the day with friends you just made. brbrbrThe unit has two large bedrooms with the primary having a king size bed, two night stands, walk in closet, linen closet, large chest, dresser, TV, DVD player, ceiling fan (remote) and an in suite bathroom, tub and shower. The second bedroom contains two double beds, a chest, desk, a wall mounted TV, a night stand, closets, (clothes & linen) ceiling fan/light (remote and chain) and an in suite bathroom with walk-in shower.brbrbrThe living area consists of a fully equipped kitchen with refrigerator, (ice & water in door) stove, microwave, dishwasher, coffee maker/Keurig, toaster oven and everything you would need to prepare meals and drinks if required. The dinette set seats 4 on raised stools/chairs accentuated by a lovely chandelier. The living room area contains a large sectional coach with recliners on each end with two stationary (arm less) chairs with storage/USB ports compartments available for your use separating the recliners and chairs. The center curved seat connects the two sections allowing for additional seating. There is another freestanding recliner, butler cabinet, small lamp, coffee table small utility table, ceiling fan/light (remote) and floor lamp. Facing you as you relax, from an adventurous day of shopping, exploring the area, or enjoying the beach, is a 60 inch flat screen television, DVD player and storage unit holding cocktail glasses of all types for adult beverages plus an additional storage/book cabinet with some interesting reading material.brbrbrif you enjoy sitting outside in the privacy of your own balcony and enjoy the Florida weather on a quiet street Then this is the condo for you.brbrbrThis area of Sarasota has everything available to you and within walking and/or driving distance. Shopping, dining, boating, golfing, sightseeing, beaches, etc. are within easy reach. Siesta Key/Beach within a short drive. Ringling Museum, Art Gallery, Mansion and Gardens within 5 miles. brbrSt. Armands Circle is rooted in culture. With just a casual stroll around the Circle, you will discover Sarasota’s unique history steeped in the Ringling family’s love of the arts.brWalk amongst statues and monuments from the past. A notable sight to see, located in the inner circle at Central Park, is the Ring of Fame, where homages to circus greats can be found in clusters along the outer sidewalk.brbrArea attractions are within easy driving from St. Armand’s, including Bush Gardens, Venice, Tampa, Tarpon Springs and many more. brbrbrIt is a great advantage to be right on St. Armand's Circle near Lido Key. Dining, shopping and strolling are nearly at your doorstep, but not too close. The white-sand beaches are a block from the Kingston Arms condos, saving effort, time and fuel. The environmentalists will appreciate this along with turtle nests, bird habitats and seashells just a short walk down the beach.brbrbrJohn Ringling, of circus fame, bought property called St. Armands Key in 1917 and proceeded to develop it. He aimed for a European-like setting and atmosphere, and given its current popularity, he must have succeeded. The Ringling Museum is just down John Ringling Boulevard in Sarasota with fine art and circus memorabilia. brbrbrDowntown Sarasota is a short drive across the water from Lido Key and offers a great many cultural interests like ballet, symphony and fine arts. The museum and various galleries contain notable works and exhibits. There are a host of festivals throughout the year for food tasting, specialty cars and other community events. brbrbrBack on St. Armands Circle, upscale restaurants await. There are plenty of casual dining places as well, but the fine cuisine of The Columbia is well worth a visit. Many diners rave about the crusty Cuban bread, which is divine, but this place knows what to do with chicken. In business since 1905, The Columbia is better than ever. Cafe L'Europe offers fine French cuisine, and Lynches Pub and Grub is great for an Irish nip afterwards. brbrbrWorking up an appetite for the many kinds of tempting foods here is no problem. Even off the beach, shop-til-you-drop is a workout when trying to see so many different stores. Clothing for the whole family, fine jewelry and boutique items lure shoppers along the circle everyday. Beachwear and other water accoutrements are easily found.brbrbrKingston Arms condos on St. Armands Circle allow residents and visitors access to these amenities day and night. They're in a plum position for fun and entertainment as well as beach access. Come on in and relax. brbrhttps://www.travelawaits.com/2561860/st-armands-circle-best-things-to-do/
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Exceptional(10)

$168.37

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Canalfront Siesta key entire King suite

Sarasota, Florida, United States

North end of Siesta Key. 850 square foot unit with king suite, excellent place for drop a line or dip a paddle, located in a quiet Neighbourhood on bayou Louise lane, The guest has a complete separate entrance and entire place. Allowing you to enjoy the full privacy during your stay . guests can ride a kayak to Sarasota bay, an old town tandem kayak is complimentary for our guests, ride to lido key and Roberts bay in minutes! A spacious dedicated parking space, self check-in with code (keyless ) makes arrival easy and flexible. The entire place equipped: kitchenette, k cups machine with coffee provided, also tea and instant coffee . steps free entry level. 2.6miles to Siesta beach. The unit has direct water access (30 feet) br Special Discount for US Veterans and Active Service Membersbrbrwe are grateful for the dedication and sacrifices made by those who serve our country. As a small token of our appreciation, we are pleased to offer a 10% discount to retired veterans and active-duty military personnel staying with us.brbrIf you qualify, please let us know when making your reservation or message us before booking so we can apply the discount to your stay.brbrThank you for your service — we look forward to hosting you and making your stay memorable!brbrPlease note that the ceiling height throughout the unit is approximately 6’9”. There are also a couple of beams where the clearance is lower, about 6’5”. Most guests find the space comfortable, but taller guests may want to be mindful in these areas. We want to make sure everyone is fully informed before booking.
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