Home Vacation Condo Rentals By Owner In Siesta Key, FL

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$133.37

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Siesta Key Waterfront Condo on Turtle Beach Inlet. Fish, Swim & Boat just Steps from Your Door. The

Siesta Key, Florida, United States

Perfect location to relax and enjoy your tropical vacation or get away from the cold northern winters. Comfortable 2 bedroom, 3rd floor condo located directly on Turtle Beach Inlet where you can fish, swim, and boat just steps from your door (pre-approval required for boat docking).brbrEnjoy dazzling sunsets from the large covered screened & glassed lanai with beautiful water views. Comfortable seating in the living room with a sleeper sofa provided for short term overnight guests. Dining area provided in the condo, and an additional dining area on the lanai. Well stocked kitchen with dishwasher. Heated pool and laundry facilities on-site. Free WiFi & Cable are provided.brbrThe southern end of Siesta Key is convenient to shopping on and off the island, and island nightlife, while still enjoying a peaceful and quiet environment. Bring your boat, or rent one from the nearby marina (free docking for residents with pre-approval). Take a 5 minute stroll to Turtle Beach, dining at waterfront restaurants and night time entertainment. Hop on the free Siesta Key Breeze Trolley and take a ride to Siesta Key Village and Crescent Beach.brbrRENTAL POLICY: One month minimum is required and it must be the first day of the month to the last day of the month unless management approves an exception prior to booking. Rents 1st day of the month to last day of the month only
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$283.15

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Updated Condo with Beach Access! Shared Pools, BBQ Area! Jamaica Royale Unit 053

Siesta Key, Florida, United States

Jamaica Royale 053 by Tropical Sands AccommodationsbrbrWelcome to Jamaica Royale 053, a newly renovated 1-bedroom, 1-bath coastal condo located within the popular Jamaica Royale beachfront complex on Siesta Key. Managed by Tropical Sands Accommodations, this bright and inviting retreat offers the perfect balance of comfort, convenience, and relaxation. Just steps from private beach access to world-famous Siesta Key Beach, consistently ranked among the best beaches in the U.S. Ideal for couples or small families, this unit delivers the ultimate island getaway for guests seeking a laid-back stay in paradise.brbrHighlightsbr• Beachfront gated complex with private beach accessbr• 3 shared heated pools within the communitybr• Newly renovated interior steps from the poolbr• Walking distance to pickleball courtsbr• Community shuffleboard and BBQ grilling areasbr• Onsite laundry facilitiesbr• 7-night minimum stay requiredbr• Close to Siesta Key Village shops, dining, and nightlifebr• 1 assigned parking spacebrbrStep into your relaxing coastal escape where lush landscaping, swaying palms, and serene Gulf breezes welcome you to the Jamaica Royale lifestyle. Spend your mornings lounging poolside or strolling to the beach for a swim in the turquoise Gulf waters. Challenge friends to a friendly game of pickleball or shuffleboard, then enjoy a casual cookout at one of the community BBQ stations.brbrInside, the newly updated condo features fresh coastal decor, modern finishes, and comfortable furnishings designed for easy vacation living. The open-concept layout includes a spacious living area with a queen sleeper sofa, a flat-screen TV, and direct access to the dining space and fully equipped kitchen; complete with a full-size refrigerator, stove, microwave, coffee maker, and all essential cookware.brbrThe primary bedroom offers two queen beds, crisp linens, and plenty of storage, while the updated bathroom includes a walk-in shower and beach-chic accents.brbrSleeping Arrangementsbr• Primary Bedroom: 2 Queen Bedsbr• Living Room: 1 Queen Sleeper Sofabr• Bathroom: Full bath with walk-in showerbrbrWith private beach access, on-site amenities, and proximity to Siesta Key Village’s boutiques, restaurants, and nightlife, Jamaica Royale 053 provides everything you need for an unforgettable island vacation.brbrBook your stay today and experience Siesta Key’s coastal charm with Tropical Sands Accommodations!
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$353.07

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Unmatched Gulf Views & Beachfront Bliss at Fisherman’s Cove

Siesta Key, Florida, United States

Welcome to your own slice of paradise! This stunning Gulf-front condo offers the ultimate Siesta Key getaway, located directly on beautiful Turtle Beach with the sand and shoreline just steps from your door. Few resorts can match this incredible beachfront location and breathtaking proximity to the Gulf.brbrTucked away on the peaceful southern end of Siesta Key, this enchanting retreat is the perfect place to relax, recharge, and create unforgettable vacation memories.brbrWake each morning to panoramic Gulf views and the soothing sounds of waves just outside your windows and private lanai. From nearly every room, sparkling water views provide the perfect backdrop for your coastal escape.brbrThis beautifully appointed first-floor condo features two spacious bedrooms, each with its own full bathroom, TV, generous closet space, and comfortable, luxurious bedding. The primary suite offers a king-size bed with a plush memory foam topper for ultimate relaxation, while the guest bedroom includes a queen bed and twin sleeper — perfect for families or additional guests.brbrThe cheerful, fully equipped kitchen features a flat glass-top stove, refrigerator with ice maker, and everything needed to prepare meals with ease. Enjoy dining indoors or unwind on your private lanai overlooking the Gulf. Beautiful ceramic tile throughout the kitchen and living areas creates a bright, clean, and inviting open-concept living space.brbrSleeping Accommodations:br• Primary Suite: King Bedbr• Guest Suite: Queen Bed + Twin SleeperbrbrExperience the beauty, tranquility, and charm of Gulf-front living on Siesta Key — your perfect beach vacation awaits!
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$343.03

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Gulf-Front Serenity at Fisherman’s Cove

Siesta Key, Florida, United States

Just bring your swimsuits, flip flops, and some groceries…everything that you might need is located in this totally updated family condo on Siesta Key!brbrCompletely renovated in 2026 with:br*Custom kitchen with all new appliances-wall oven, cooktop, microwave, refrigerator, and dishwasherbr*Granite countertop with bar seating and highlighted LED lightingbr*Totally equipped kitchen for any style of meals + gas grill near bay for your barbequesbr*Fresh and new coastal decor-new tile, doors, trim, all new furniture, and freshly paintedbr*New TV's with Comcast cable and wifi service br*New washer and dryer and hotel style safe are located in the master bedroom walk in closetbr*Master bedroom suite with king bed and true walk-in shower without any step or entry lip-everything is newbr*Guest bedroom suite is private via the barn door entrance and features both queen and twin beds, bath w/tub-shower, and granite toped vanitybr*A high chair, booster seat, and pack and play (with bedding) are providedbr*Free boat docks on the bay side for fishing brbrBed set up: 1K, 1Q and 1TbrbrA toes in the sand experience-we have 2 private lounge chairs, and 6 additional beach chairs, umbrellas, beach towels, and a cooler- our private white quartz beach area just at your doorstep! And just adjacent is the larger Turtle Beach area for shelling, fishing, and park area with kayak, paddleboard rentals, wonderful children's playground, and a sand volleyball court.brbrA free trolley will take you north to the Siesta Key village, Siesta Key Beach, and the mid-island area of restaurants and shops.brbrThe highlight of your memories will come from the sounds of the waves and the beautiful sunsets! We welcome you to our family vacation home that we have cherished for 22 years, and hope you will return in years to come as well.
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$249.0

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Dog-Friendly, Boat Dock, Heated Pool, Walk to Beach

Siesta Key, Florida, United States

Adorable, dog-friendly 2nd floor condo in walking distance to Siesta Key's main public beach which consistently ranks as one of the top beaches in the world with fine white quartz sand that stays cool on the hottest of days, and calm turquoise Gulf water. There is a concession stand, tennis courts, playground and outdoor showers. Beach towels and essentials provided for your stay! The free trolley takes guests to numerous stops along Siesta Key.brbr•Ideal Siesta Key location just a short 5-minute stroll to the island’s #1 rated beach and convenient access to community tennis and pickleball courts.brbr•Dog-friendly property – welcomes one small dog (25 lbs or less), so your furry friend can join the fun!brbr•Located on the second floor of a quiet, well-maintained community that’s perfect for relaxing after a day in the sun.brbr•This nicely updated 1-bedroom, 1-bath condo offers a bright and beachy interior, thoughtfully designed for comfort and ease.brbr•The spacious primary bedroom includes a comfortable king bed, large closet, and coastal-inspired decor that invites peaceful rest.brbr•Updated full bathroom features a walk-in shower, modern fixtures, and fresh finishes. Bathroom essentials and plush bath towels are provided for your stay. brbr•Enjoy the tropical breeze from your screened-in lanai, the perfect spot for morning coffee or a sunset drink.brbr•A rare amenity in the area: your own private boat dock, ideal for boating enthusiasts looking to explore the Intracoastal Waterway.brbr•Take a dip in the heated community swimming pool, surrounded by palm trees and lounge chairs for sunbathing and relaxing.brbr•Make dinner alfresco with community BBQ grills and shaded outdoor dining tables, perfect for grilling up your fresh catch.brbr•Well-equipped kitchen with full-size appliances, cookware, and utensils, making meal prep a breeze during your stay.brbr•Open-concept living and dining area with comfortable seating, a dining table for four, and plenty of natural light.brbr•Cable and WiFi included, along with a flat-screen TV in the living area for evening entertainment.brbr•Laundry facilities available on site for added convenience during extended stays.brbr•Free assigned parking and guest spaces ensure easy arrival and departures.brbr•Short trolley ride to Siesta Key Village with its fun mix of restaurants, shops, nightlife, and local charm.brbr•Whether you're lounging poolside, boating from your dock, or catching the sunset on the beach, this is the perfect Siesta Key escape for couples or solo travelers – and their pup!
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$348.96

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Siesta Key short walk to white sands of the gulf, steps to Dining & Live Music

Siesta Key, Florida, United States

Welcome to your perfect Sista Key Escape! brbrThis comfortable 2-bedroom, 2-bath condo is just a short walk to the world-famous white sand beaches, has a heated pool and is only steps from popular restaurants, bars and live music.brbrLocated on the 2nd floor, this condo offers a relaxed coastal feel with many updates, new appliances throughout and an unbeatable location.brbrThe open living and dining area is bright and inviting , featuring Fjord reclining chairs from Norway -perfect for relaxing after a day at the beach. The primary bedroom offers a king bed and en-suite bathroom, while th second bedroom features two twin beds, ideal for family or guests. A Pack 'n Play is also available for infants or toddlers. Whether you’re curling up inside or stepping out to explore, this wonderful spot offers a peaceful retreat. Enjoy all that Siesta Key has to offer when you stay.brbrEverything you need for a perfect beach day is provided, beach chairs, umbrella, cooler, Turkish towels and beach toys. brbrThe free Siesta Key Trolley stops nearby and provides easy access to Siesta Key Village, Turtle Beach,Siesta Key Public Beach and off the island. brbrStep outside and enjoy one of the best locations on Siesta Key. You are just steps from local favorites like Miguel's, Captain Curt's, as well as nearby restaurants offering both casual dining and live entertainment. brbrPlease note: This is a second floor unit with no elevator.
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Exceptional(1)

$188.94

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Spacious Water View 2nd Floor Unit 5 Minute Walk to Siesta Beach

Siesta Key, Florida, United States

White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.brPlease note: THE MINIMUM RENTAL PERIOD IS 14 DAYS.brOur condominium is privately owned and decorated, unique and beautifully maintained. Check out the amenities and photos!brOur unit has an assigned carport. brWhy just go to Florida when you can visit the #1 Beach in the USA! White Sands Village is a short 0.3 mile from Siesta Public Beach. No need to worry about Beach Parking while staying here at White Sands Village.brbrSiesta Beach: Rated 2021 #1 beach in Florida by Holidu https://www.bizjournals.com/tampabay/news/2021/06/23/siesta-key-beach-named-no-1-beach-in-the-state.html, 2020 Tripadvisor #1 beach in the USA https://www.sarasotamagazine.com/news-and-profiles/2020/08/siesta-key-beach-named-no-1-in-the-country-again-tripadvisor , Dr Beach 2017 #1 beach in the USA https://www.drbeach.org/2017-siesta-beach-sarasota-floridabrbrSORRY, BUT NO PETS ALLOWED.brbrThe condo is NOT ADA ACCESSIBLE. NO SMOKING.brbrThe first sign that White Sands Village is the right place for you are the grounds, seven acres beautifully landscaped with palm trees, live oaks, flowering shrubs and tropical flowers.brOur pool is heated year-round to a warm 86º, so you can enjoy a swim even during the cooler months. Catch a bit of sun on a lounge chair, or sit in the shade and enjoy a bit of vacation reading.brPublic tennis/pickleball courts are just across the street.brFour lighted gas grills, on the White Sands property, are available for your use.brOne covered parking space is provided for each unit, with additional parking available.brLaundry facilities are available at four locations.brLinens are supplied and kitchens are fully equipped in each of our one- and two-bedroom rental units.brSit by the peaceful lagoon connected to the Intracoastal Waterway.brIn addition to the stunning Siesta Key Public Beach, there are two additional Gulf of Mexico beaches on Siesta Key, as well as great little shops and restaurants. You’ve got easy access to boat rentals, jet ski rentals, parasailing…recreation awaits you!brCrescent Beach, just south of the public beach, is a quieter and more private beach, with only one public access road. Its southern tip is the Point of Rocks, a great snorkeling and diving area with coral reefs that often harbor abundant marine life.brTurtle Beach, south of Crescent Beach, is a great family play area, with a playground, horseshoe pit, boat launch, volleyball court and picnic tables. It’s also a good place for finding shells and perhaps some shark teeth. Here you can launch your boat, fish in Blind Pass Lagoon, or eat in a nearby restaurant.brSiesta Key Village is full of shops and restaurants. You can buy just about everything you need to enjoy your beach vacation, including beachwear, sun products, and toys. There are also little boutique shops where you can indulge your love of unique clothing, jewelry, flowers and scented lotions. Several local restaurants offer patio dining, which you can enjoy from breakfast spots to dinner and evening entertainment.
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$198.88

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Charming 1-bedroom in Siesta Key with AC WiFi. 5 min walk to #1 America's Beach

Siesta Key, Florida, United States

Welcome to your newly renovated dream coastal escape in beautiful Siesta Harbor on Siesta Key, Sarasota, Florida, USA! This turnkey furnished; spacious one-bedroom, two-bath condo featuring brand new furniture is available now through October 2025. Perfectly situated along a peaceful canal, it offers stunning water views and a truly relaxing atmosphere. Just a short 5-minute stroll, you'll enjoy deeded access to Siesta Key's world-famous beach. Step inside to find a bright, updated kitchen with granite countertops, stainless steel appliances, luxury tile throughout, and beautifully renovated bathrooms. Enjoy morning coffee or an evening glass of wine on your screened-in patio that overlooks the canal, providing the perfect spot to unwind while watching boats drift by. It's a serene, shaded retreat that truly brings the outdoors in. Each floor has easy access to elevators and free and well-appointed laundry room. Siesta Harbor is a welcoming community offering a wide range of amenities, including: * Outdoor spa and shower * Indoor sauna * Fitness room * Shuffleboard court * Clubhouse * BBQ area *Library * Take a dip in the heated pool and spa, or cast a line from the dock and fishing pier. Whether you're seeking a peaceful retreat or a vibrant coastal lifestyle, this condo has it all. Just bring your suitcase and start enjoying the laid-back beach life!br30 days minimum stay.
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$450.7

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Gulf and Bay Club- C611 by Tropical Sands Accommodations

Siesta Key, Florida, United States

Gulf and Bay Club- C611 by Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit C611 — your sun-soaked escape in one of Siesta Key’s most sought-after beachfront communities. This bright and airy 3-bedroom, 2-bath condo is just moments from the sand and surf, offering the ideal setting for a relaxing long-term getaway.brbrHighlights:br • Less than 5 minute walk to the beachbr • Pool Tablebr • Community Pool and Hot Tubbr • Community Fitness Centerbr • Community Tennis and Pickleball CourtbrbrComfortably accommodating up to six guests, this condo is designed for both relaxation and convenience. The primary suite features a plush king bed and private ensuite. The second bedroom includes a cozy twin bed, while the third offers a versatile futon with a trundle — great for kids or extra guests. A second full bathroom is located off the hallway.brbrBedrooms and Bathrooms:br- Primary Bedroom: King Bed, Ensuite Bathroombr- Second Bedroom: Twin Bed, Hallway Bathroombr- Third Bedroom: Futon Bed, Hallway BathroombrbrAdditional perks include a private washer and dryer, high-speed Wi-Fi, and covered parking. While pets are not permitted, you’ll have full access to Gulf and Bay Club’s impressive amenities — from shuffleboard and tennis to a tranquil hot tub and fitness center.brbrWith a 28-night minimum stay, Unit C611 is your perfect home base for snowbird season, remote work, or an extended dose of island life.brSettle in, unwind, and let your Siesta Key story begin.
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$163.07

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The Blue Luna | Private Villa w/ Access to Pool & Pier, Walk to Siesta Beach

Siesta Key, Florida, United States

Welcome to The Blue Luna, a serene stand-alone villa nestled in the tropical paradise of Polynesian Gardens on Siesta Key. This two-bedroom, two-bathroom home has been thoughtfully decorated with a calming, coastal blue palette that reflects the soft light of the moon on the water. The spacious living area is bathed in natural light, inviting you to relax and unwind. The primary bedroom features a king-size bed and an elegant ensuite bathroom, offering a private haven for rest. The second bedroom, with its twin-size and double-size bed, is perfect for families or friends ready for a peaceful retreat. Start your day by watching dolphins play in the water as the sun rises, then take a refreshing dip in the nearby heated pool. For a more adventurous afternoon, cast a line from the community fishing pier for the catch of the day. As evening approaches, prepare to be enchanted by the breathtaking Siesta Key sunsets and the rhythmic sounds of the local drum circle celebration—a truly magical tradition. Located within walking distance of vibrant restaurants, bars, and attractions, you'll find plenty to do without ever needing a car. At The Blue Luna, you can relish the stunning sunsets, lose yourself in the rhythmic beat of the drum circle, or simply enjoy a quiet moment by the pool. Book your stay today and claim your slice of paradise where the magic of the moon meets the tranquility of the sea.brbrGood to Know for Your Stay:br• Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay.br• Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment.br• Pet Policy: To adhere to HOA guidelines, pets are not permitted at this property.br• A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!
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$181.99

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Quiet condo with a heated pool & central AC - short walk to the beach

Siesta Key, Florida, United States

Sea- Esta' Winds 209brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrLocated just south of the Stickney Point Bridge, this second-floor condo provides a lovely place to rest during your trip to Siesta Key! No car is needed during your stay - this vacation rental is less than a half-mile walk to Crescent Beach public access!brbrNatural light flows through this space, and you can kick back and relax in the central air conditioning within the brightly painted walls. It's a corner condo within the complex with no unit above, so guests can enjoy plenty of peace and quiet. Cook up tasty meals in the well-equipped, full kitchen with all-new appliances, then dine together at the built-in table for four. This home has a Roku device with Guest Mode for you to enjoy. Bring your favorite subscriptions and easily sign in to enjoy. You can also enjoy hundreds of free movies, TV shows, news and more. You and your guests can also enjoy access to a shared and heated pool during your stay.brbrRESORT AMENITIESbr- Outdoor, heated poolbrbrTHINGS TO KNOWbrGuests must book for a minimum of two weeksbrShared laundry facilities available on-sitebr*POOL WILL BE OUT OF SERVICE FROM 05/05-06/15brbrParking notes: There is free parking available for 2 vehicles.brThis rental is located on floor 2.brbrDock details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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