Home Vacation Condo Rentals By Owner In Sarasota, FL

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$201.87

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NEW LISTING Relax at Redwood, Close to Siesta Key Beach, Pool

Sarasota, Florida, United States

Summary:brbrImagine waking up just minutes from the powder-soft sands of Siesta Key Beach, brewing fresh coffee at your private coffee bar, and deciding whether today is a beach day, a pool day, or a Gulf Gate dining night.brbrbrbrThe Space:brbrWelcome to your relaxed coastal retreat at Relax at Redwood — brbra second-floor, pet-friendly getaway perfectly positioned between Siesta Key brbrand the local charm of Gulf Gate.brbrbrbrThis bright 1-bedroom, 1-bath condo comfortably sleeps up to 4 guests and is brbrideal for couples, small families, snowbirds, or long weekend beach escapes.brbrbrbrTHE SPACEbrbr• Second-floor unit (stairs required, no elevator)brbr• 1 private bedroom with comfortable beddingbrbr• Sleeper sofa in living room (sleeps up to 4 total)brbr• 1 full bathroombrbr• Open living and dining areabrbr• Fully furnished kitchen with cookware, dishes, and essentialsbrbr• Dedicated coffee bar for your morning brewbrbr• Pet friendly (1 pet max)brbrbrbrPlease note: The unit is located on the second floor and requires steps to access. brbrIt may not be suitable for guests with mobility limitations.brbrbrbrThe Neighborhood:brbrCOMMUNITY AMENITIESbrbr• Community poolbrbr• Firepit lounge areabrbr• Outdoor grillbrbr• Relaxed tropical settingbrbrbrbrGetting Around:brbrPRIME LOCATIONbrbr• Siesta Key Beach – approx. 5–10 minutesbrbr• Gulf Gate dining & shopping – approx. 5 minutesbrbr• Siesta Key Village – approx. 10 minutesbrbr• Downtown Sarasota – approx. 15 minutes
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$317.53

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Kingston Arms 3A in Sarasota

Sarasota, Florida, United States

Lido Key Dream Vacation Rental! Newly remodeled and tastefully furnished, 2 bed, 2 bath condo at the highly desirable Kingston Arms. No need for a car, walkable to the sparkling sands of Lido Beach and all the wonderful locally owned Restaurants and Shops on the Historic St. Armand's Key or hop on the BayRunner Trolley to downtown Sarasota! No expense was spared in the renovation, all tile throughout, a gorgeous new kitchen with all new appliances, cabinets and lovely granite counter ...tops. The main living area has comfortable seating, a smart TV, dining for four or more and overlooks a quiet residential street. The Primary bedroom has a King bed, walk in closet, a smart TV, a full bath and expansive windows, so very light and bright. The guest bedroom has a Queen bed, a desk, and the bath is en suite. You will enjoy your morning coffee on the screened Lanai and walk to the beach for gorgeous sunsets! Welcome to Paradise! Weekly rates are available for off-season bookings too!For additional details contact Stephanie Deshaies at or email contained herein deemed reliable but not guaranteed. ***brbrAmenities Include:brbr- Bldg. Complex Name: Kingston Armsbrbr- Type Unit: Lowrisebrbr- Unit Rating: Silverbrbr- Beach Access Type: Walk tobrbr- Distance to Beach: 1.5 Blocksbrbr- Elevator: yesbrbr- Floor/Bldg Height: 1/2brbr- Year Built: 1963brbr- Approx. Sq. Ft.: 1034brbr- Exposure/View: South/Residential Streetbrbr- Pool/Spa: Yes communitybrbr- washer dryer: Y/communitybrbr- Parking Type: 1 Carport spacebrbr- Lanai / Balcony: Screenedbrbr- Master Bedroom: Kingbrbr- Bathrooms-Master: Shower onlybrbr- Guest Bedroom: Queenbrbr- Bathrooms-Guest: Shower onlybrbr- TV/Dvd/ Stereo: 2 TVsbrbr- Internet Access: Wifibrbr- Listing Advisor: Stephanie Deshaiesbrbr- Min. Rental # x perYr: 12 times a year/1weekbrbr- Security Deposit: $750brbr- Reservation Fee: $170brbr- Damage Protection: $60brbr- Departure Clean Fee: $200brbr- Taxes: 13%brbr- Utility Charges: Incl. $75 cap on off season monthly rentalsbrbr- Rate - Monthly: $6,000/$3500brbr
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Exceptional(5)

$164.33

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Luxury Condo Living on Sarasota Bay, Minutes From Downtown - Admirals Watch

Sarasota, Florida, United States

Welcome to Admirals Watch, a sophisticated sanctuary on the 5th floor of The Strand, Professionally managed by Gulf Coast Vacation Rentals, minutes from downtown Sarasota. Imagine waking up in your luxurious one-bedroom, two-bathroom retreat next to Sarasota Bay with all of Sarasota's attractions at your doorstep.brbrFrom the moment you step inside, you'll be embraced by bright, modern interiors. The primary suite offers luxurious touches, including a spacious walk-in closet and a sleek ensuite bathroom with a walk-in shower. Down the hall, a second bathroom and a versatile den with a Murphy bed await, ready to transform into extra sleeping space or your dream remote workspace.brbrThe heart of the home, the living area, radiates with natural light. It opens onto a private balcony where you can sip your morning coffee, savoring views of the pool and Sarasota Bay. In the evenings, relax with a glass of wine as you witness the stunning Gulf sunsets. The modern kitchen, equipped with stainless steel appliances, is perfect for crafting gourmet meals, while the dining area comfortably seats four.brbrAt The Strand, you'll enjoy a host of high-end amenities including a resort-style pool and spa, a fitness center, and a fire pit. For the adventure seekers, there's even a kayak launch! Plus, you're just moments away from Downtown Sarasota, with its world-class dining, shopping, and cultural experiences.brbrParking is a breeze with two reserved spots: one in the building's garage (Spot #129) and one outside near the pool (Spot P-229). Admirals Watch is conveniently located in the first building, 1703, upon entering the gate, offering a prime location that perfectly balances tranquility with easy access to the vibrant city life.brThis is luxury living at its finest—welcome home!brbrHouse Rules: No smoking or burning candles inside the lodging. No parties. No Pets. Amenity fob and keys must be left in the unit prior to departure to avoid a $150 fee. Your reservation may require you to fill out a Home Owners Association application that may request personal details. Any application fees required by the HOA are non-refundable.
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$339.88

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Siesta Key 3 bed/ 2.5 bath Penthouse, private roof top deck, parking, boat slip!

Sarasota, Florida, United States

Summer season is available now! July - Oct. 2025 brPeak season Nov. 2025 - April 2026 is $55,000 total.brThis highly sought after 3-bedroom, 2 1/2-bath Penthouse with private hot tub roof deck end unit, nestled in the heart of Siesta Key, offers an extraordinary living experience. Situated in the #1 Beach in the U.S., this gem is available for furnished seasonal or annual rental. This corner end unit is flooded with natural light from nearly every window, sweeping views from the Intracoastal waterway to the Gulf. A spiral staircase in the Florida room, leads to a rooftop deck where you can savor a glass of Champagne in the rooftop jacuzzi while witnessing the breathtaking sunset over the Gulf. brAfter a sun-soaked day at the beach, unwind with friends and family around the outdoor fire pit. Three outdoor grills are at your disposal to cook up the day's fresh catch. The luxurious Master Suite boasts a separate shower and Jacuzzi tub, providing a perfect retreat. The recently updated gourmet kitchen with maple cabinets, granite counters, and a breakfast bar comes fully stocked for your culinary enjoyment. If you need to attend to work matters, there are three dedicated working spaces within the unit. brThere is a clubhouse with a tennis court, two pickleball courts and a pool overlooking the Intracoastal, providing a perfect setting for recreation. The unit comes equipped with all the necessary gear for tennis, pool, and beach activities. One covered parking space and ample additional parking for guests ensure convenience. Another covered parking space is also additionally available. For boating enthusiasts, a private boat slip is additionally available, accommodating boats up to 30 feet. Deeded beach access is conveniently located just across the street, within a short walking distance. Small pets are permitted with the owner’s approval. brAll utilities are included with a 6-month+1 day seasonal rental, making this penthouse a complete package for those seeking an unparalleled Siesta Key living experience. One year rental is also available. Dishwasher, laundry and dryer, microwave, toaster oven, coffee maker, refrigerator and freezer, ice maker, three T.V.'s and elevator access.brSummer season is available now! July - Oct. 2025.brPeak season Nov. 2025 - April 2026 is $55,000 total.
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Exceptional(13)

$420.86

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Steps to Siesta Key Beach! We offer 3-night rentals! Beach gear included!

Sarasota, Florida, United States

Location! Location! Location! Sea Shell Condos Unit #105 is in the BEST spot on Siesta Key. It's just steps to the cool white sands of the nation's #1 beach. Across the street are restaurants, bars, ice cream and coffee shops, and even a grocery store! This is one of the few areas where you could spend an entire vacation and never need a car. brbrWe provide our guests with all the amenities they need to enjoy the beach. That includes beach chairs, umbrellas, toys, boogie boards, beach towels, and a wheeled cooler. Less packing and no need to purchase those items after you arrive saves money and time. brbrOur coastal-themed condo has a fully stocked kitchen, a King bed in the master, with a blackout shade, 2 full beds in the 2nd bedroom, and a queen pull-out couch in the living room to comfortably sleep 6. Both bedrooms feature an en suite bath. The dining table seats 6 and there are additional seats at the breakfast bar. In addition to celing fans in reach room, we provide stand fans as well. We do not have a beach view, but that allows us to rent at a slightly lower price point than the front units. brbrOther amenities include coffee, both ground and pod, salt, pepper, spices, and plenty of condiments. We leave some surprise goodies too! brbrThe spacebrbrOur unit, #105, features easy access to the elevator and large, heated pool. Access the private beach with your gate code and enjoy the soft sand, gentle waves, and beautiful sunsets. Great restaurants within walking distance include Captain Curt's (famous clam chowder), Sniki Tiki (music every night), Anna's Deli (awesome sandwiches), Toasted Mango Café for breakfast, Clayton's, Daquiri Deck, Spearfish Grille, and more. There are ice cream, coffee shops, and mini donuts as well. There's even a grocery store with an awesome premade food selection. A free trolley takes you to Siesta Key Village for even more shops, restaurants, and bars. brbrGuest accessbrLaundry room is just around the corner from the condo.brbrPool with restrooms.brOther things to notebrMUST BE 25 YEARS OLD TO RENT - NO EXCEPTIONS!brNo Pets allowed.brNo smoking in unit or on balcony.brWhile we are very close to the beach, we do not have a beach view due to our lower floor location.brPlease do not rearrange the furniture.
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$551.32

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Location, location! Private Beach, Gulf Views from Balcony, Heated Pool, Siesta Sands with King Bed

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 Siesta Sands Beach Resort 4th Floor with Elevator! brbr brbrThis gorgeous south-end Siesta Key condo sits on the Gulf of Mexico in a gated complex with private beach access and two heated pools. Enjoy endless beach activities—swim, build sandcastles, rent jet skis, or relax under an umbrella with a good book. Take in stunning sunsets, collect seashells, or simply lounge poolside for the ultimate coastal getaway. brbr brbrLOCATION HIGHLIGHTS: brbr- South end of Siesta Key, on the Gulf of Mexico brbr- Gated beachfront complex with private beach access & shower brbr- Easy access via South Siesta Key Bridge brbr- Free island shuttle to Siesta Village brbr- Close to shops, restaurants, and cafes brbr- Two heated community pools with loungers brbr- BBQ grills and shaded pool areas brbr- Community outdoor exercise/TV/lounge area brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom 4th floor condo (1196 sq ft) brbr- Coin laundry on each floor (no in-unit washer/dryer) brbr- One assigned parking under building (narrow, not fully covered) brbr- Elevator & stairs access to unit brbr- Secure WiFi & cable included brbr- Private beach access: area closest to the building is reserved for guests renting on-site beach equipment, set up by water line or public beach space brbr brbrLIVING ROOM: brbr- Beachy, open living area with two leather sofas (one queen sleeper), cozy armchair, large Smart TV brbr- Sliding doors to private balcony with Gulf views brbr- Outdoor dining for 4 on balcony brbr brbrKITCHEN & DINING brbr- Fully equipped kitchen with stainless appliances brbr- Stone counters & breakfast bar (seats 3), dining table (seats 4) brbr brbrBEDROOMS & BATHROOMS brbr- King Master Bedroom: balcony access, flat screen TV, ensuite bath with dual sinks, granite counters, walk-in tiled shower brbr- Queen Guest Bedroom: flat screen TV, ceiling fan, easy access to guest bath with updated tile and granite countertop brbr brbrEXTRA PERKS brbr- Beach accessories: a couple of chairs, an umbrella, beach towels, and cart brbr brbrLOCAL FAVORITES brbr- Walk the beach every evening, collect shells, or swim in the Gulf brbr- Rent jet skis, go fishing, or enjoy nearby family activities brbr- Nearby public & private beaches, shops, restaurants, and cafes brbr- Perfect sunsets from the balcony or beach brbr brbrIMPORTANT INFO brbr- Maximum occupancy: 6 people (including visitors and common areas) brbr- Non-smoking unit. No pets allowed brbr- One assigned parking space; limited guest parking first-come, first-serve. Assigned spot is tight, not ideal for larger vehicles brbr- Parking restrictions: no boats, motorcycle, trailers, jet skis, oversized or commercial vehicles allowed. brbr- Beach may be crowded during peak times (beyond owner control) brbr brbrMAKE YOUR BEACH DAYS OFFICIAL—BOOK YOUR STAYbrbrWe 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(24)

$230.21

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Condo# 409 Steps from Siesta Key Beach Condo

Sarasota, Florida, United States

** This unit offers reservations with a 4-night minimum from April/11/2026 through December/11/26br and April/10/27 through December/10/27** Please contact our Office for assistance.brbrRecently updated this sunny one bedroom one bath condominium has beach views and is just a two minute walk to the famous Siesta Key Beach. Come and experience the surprisingly white powdery-soft quartz sand and beautiful sunsets! The condo's screened in lanai is perfect for enjoying those beautiful sunsets or just relaxing with a book or a drink. Unit 409 sleeps 4 comfortably with a queen size bed, and queen sleeper sofa in the living room. Private WiFi and high-speed internet are provided. The newly remodeled kitchen is fully equipped with everything you might need during your stay.brbrAt La Siesta Condominiums it's a leisurely walk to Siesta Village or use the free Trolley service to its numerous restaurants, specialty shops, night life and other attractions and services. Explore nearby St. Armonds Circle on Lido Key, Longboat Key and downtown Sarasota. Onsite you can enjoy the heated swimming pool, designated outdoor grilling areas, shuffleboard court, game room with billiard, ping pong table and exercise room. For your convenience, there is your own close reserved parking space, and washers and dryers located right down the hall on the 4th floor by the elevator. Public tennis and pickleball courts, playground and volleyball courts are close by on the beach.brbrYour perfect vacation is awaiting here at this comfortable, updated condo at the famous Siesta Key Beach with incredible sunsets, magnificent views and fantastic beach.
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Exceptional(18)

$261.38

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Condo#401 Overlooks Siesta Key Beach Entrance

Sarasota, Florida, United States

Condo#401 Overlooks Siesta Key Beach Entrance brYou immediately feel like you’re on a beach vacation when you enter this condo at La Siesta. It’s a top floor, end unit that overlooks the entrance to Siesta Key Beach. After a long day at the beach, dine on the lanai or sip your favorite beverage while people-watching and gazing at the sunset. Inside 401 you will find a large, well equipped kitchen that will satisfy everyone, from those who want to chef during vacation, to those who simply want to make a good cup of coffee or blend drinks. Guests value having 2 bedrooms and 2 bathrooms, private wifi, cable, and streaming options.brbrUnlike most beaches in Florida, Siesta Key Beach has life guards to keep you safe. And no need to fight for a parking spot! Your beach experience starts pleasantly, by packing your beach wagon with chairs, cooler, and umbrella—all provided at no extra cost. After crossing the street, you enter the hub of the beach. On your left is a snack bar. Grab an adult slushy before stepping onto the powdery, white sand and heading out to the beautiful blue/green, warm Gulf water. Lastly, bring your tennis and pickleball racquets! There are free, public courts a ½ block down the street.brbrYou don’t need to rent a car because restaurants are within walking distance or accessible through the local free shuttle service that stops right in front of this unit! If you like to travel light, you will appreciate that bath towels, sheets, kitchen tea towels, and even beach towels are provided. On-site laundry can make flying with only a carryon an option for light packers.brbrLa Siesta Condo Association is a well-run establishment with in-house support if you face any challenges during your stay. With its proximity to the water, the beautiful pool, the use of the club house, and comfortable condos, staying at La Siesta is one of the best values on the island. We invite you to book your visit to Siesta Key Beach in Unit 401. The size, supplies that are provided, and location of this condo make it a perfect stay for a week or a few months! Whether you book our condo or find another-- come to Siesta Key—it is a treasure.
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$320.51

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Book Me Baby! Siesta Shores #9

Sarasota, Florida, United States

Pinkie Flamingo Welcomes You To Cloud Nine at Siesta ShoresbrKing / Queen Sleeper SofabrNew 2024 RenovationbrbrBeing on Siesta Key is one thing, but being on Cloud Nine on Siesta Key is the ultimate! Be among the first to enjoy this new 2024 renovation…all new everything. From the fresh new paint, new solid surface flooring, and new appliances to the stylish new furniture, this cozy little one bedroom / one bathroom bungalow is ready and waiting to be your go-to spot in the sun. Within walking distance to the popular Siesta Key Village, Cloud Nine is just one block off the beautiful beach as well. Load up the beach cart, 4 chairs and umbrella (all included) and choose between public beach access #7 or #8. “Where is my easy button ” asked Pinkie Flamingo. As a curator of vacation rental properties all along Florida's Gulf Coast, Pinkie knew a winner when she saw one. “This is adorable!” The private outdoor area adds to the charm, furnished with a picnic table, fire pit, conversation seating and a propane gas grill. Festive string lights set the mood for a relaxing evening under the stars. brbrLet's Head to the Beach!brbrConsistently ranked in the top beaches in America, Siesta Key enjoys a year-round appeal with everything a tourist might want close at hand…shopping, dining, beaches and fun! Siesta Key achieves its lofty position in the beach rankings among some fierce competition. 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..all within easy walking distance of this property. brbrHighlightsbr• Walk to The Villagebr• Across the street from the beachbr• Private backyard oasisbr• New renovationbr• New furnishings and appliancesbr• Solid surface flooringbr• Covered parking for 1 carbr• Outdoor showerbr• Laundry room in resort areabr• Great ACbrbrCome To Florida…For The Fun Of ItbrbrAll of Pinkie's Properties Have A Few Things In Commonbr• Must Be 25 To Bookbr• No Smoking br• Cancellation OK 30 Days Prior To Check-Inbr• Sheets & Bath Towels Included…BYO Beach Towelsbr• All Kitchens Fully-Equipped With Cooking/Eating Utensils… BYO Spices & Food
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