Home Vacation Rentals By Owner In Siesta Key, FL

Showing 180 Of 2077 Vacation Rentals
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Exceptional(1)

$421.47

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Villa

44 Premium Plus - Sandy Toes & Seaside Bliss

Siesta Key, Florida, United States

Step into luxury and comfort at our newly renovated 2-bedroom, 1.5-bathroom condo, perfectly designed for your next getaway. This vibrant space features a fully equipped kitchen ready for your culinary adventures and a private carport just steps from the unit for hassle-free parking. Recently updated in Summer 2023, the condo comfortably accommodates up to six guests with a king-sized bed, queen-sized bed, twin bunk beds, a sleeper sofa, and a pack-and-play for the little ones. Enjoy the convenience of an in-unit washer and dryer, plus high-speed private Wi-Fi. At Casa Mar, indulge in resort-style living with exclusive amenities including two refreshing swimming pools, tennis, pickleball, and shuffleboard courts for endless fun. Host memorable BBQs at multiple grilling areas with picnic tables, or unwind at one of two beach pavilions overlooking over 200 feet of pristine private beachfront. Laundry day is easy with multiple facilities throughout the community, and the Siesta trolley stop at the entrance makes exploring the area effortless. Just steps from the beach and close to the pool, grill, and laundry, our condo provides the ideal vacation oasis—with beach towels provided so you can dive into your vacation stress-free. Experience the best of beachside living at our Casa Mar retreat, where every detail is crafted for your relaxation and enjoyment.
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Sleep 6

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Exceptional(5)

$361.64

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Condo

2-Bedroom, 2 Bathroom Gulf Side #159 Siesta Key – Steps from Siesta Key Beach

Siesta Key, Florida, United States

This second floor 2 bedroom, 2 bathroom corner condominium is located on the Gulf side of the property. Because of its central location, it is a short walk to our white sandy beach, the tennis/pickleball courts, pool and charcoal barbecues. To comply with the Sarasota County Fire Code, our two bedroom units sleeps a maximum of six people. brbrThe master bedroom is furnished with two queens beds and the guest bedroom has two twin size beds, both with 32 flat screen TVs. The master bathroom has a walk in shower and the guest bathroom has a tub/shower combination. The spacious living room is equipped with a 47 Smart flat screen for your enjoyment. The lovely kitchen is fully equipped with all the items you need for cooking - pots/pans, dishes, utensils, toaster and a coffee maker. There is beautiful tile throughout the unit. The patio is an extension of the living area.brbrVacation like a King and Queen in one of Siesta Key's most luxurious resorts, The Palm Bay Club is a beach to bay resort condominium community that has an abundance of fine amenities sure to please you. This complex contains a Private Beach, beautifully manicured grounds and a tropical courtyard, fishing pier, boat slip for rent, 2 heated community pools and large custom hot tub overlooking the serene bay, a fitness center, recreation lounge, and 2 lighted tennis courts with Pickleball and charcoal grills overlooking the bay. Vacationing at Palm Bay Club will provide many memorable moments with picture perfect Bay sunrises and Beach sunsets. Plus, #1 rated famous Public Siesta Key Beach is close by.....You’ll never want to leave this fine resort! brbrBeach and pool lounge chairs are available for all guests. But you may rent a cabana on your private beach and bask in the shade by the pristine waters of the Gulf of Mexico with beautiful quartz sand.brbrPickle ball and tennis paddles are available at the clubhouse by the fitness center. There is a deposit to use the Fitness Center (this is arranged at the Front Desk). brbrThis is a waterfront (gulf front) complex spanning from gulf to bay and your private beach.brPrivate beach with cabanas to rent, lounge chairs right on Siesta Key brThe complex has strap lounge chairs for free or rent a cabana by the day or the week.brTwo Pools, Hot Tub on the BaybrTennisbrFishingbrFitness Ctr (office req. a $40 refundable fee) brBBQbrbrOnly 6 guests are allowed to stay in our unit. brbr***Don't forget to take your family photos and selfies at sunset and also on the resorts main driveway lined with beautiful palm trees. It's a breathtaking view that guests love!
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Bath 2

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Sleep 6

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Exceptional(22)

$350.74

/ Nightly
Condo

Our House at the Beach, Across Street to Main Beach Access, Tennis, Heated Pool

Siesta Key, Florida, United States

Welcome to your dream vacation retreat! This exquisite 2-bedroom, 2-bath condo is strategically located directly across the street from Siesta Key's main beach access, providing you with immediate access to the sun-soaked paradise of the Gulf of Mexico. With a prime location and a plethora of amenities, this vacation rental promises an unforgettable stay for up to six guests.brbrAs you step into the condo, you'll be greeted by a seamlessly open living space that exudes modern elegance. The floor-to-ceiling sliding glass doors not only flood the space with natural light but also unveil breathtaking views of the pool and tennis courts. The living room is a haven of comfort, featuring a plush leather pullout couch, a flat-screen TV, a love seat, and two recliners. Whether you're enjoying a movie night or simply unwinding after a day at the beach, this space caters to all your relaxation needs.brbrAdjacent to the living area is a beautiful wooden dining room table that comfortably seats six. It's the perfect spot to gather for meals, playing board games, or planning your next day's adventure. The galley kitchen, a culinary enthusiast's delight, boasts granite counters, stainless steel appliances, and pristine white cabinetry. Fully stocked with everything you need, from cookware to utensils, it invites you to showcase your culinary skills or simply whip up a quick snack before heading out to explore.brbrStep through the sliding glass doors onto the wrap-around balcony, where sun loungers and an outdoor dining table and chairs await. This is your private oasis to savor the warm Gulf breeze, dine al fresco, or simply bask in the Florida sunshine. The balcony offers stunning views of the pool, creating a serene backdrop for your moments of relaxation.brbrThe primary bedroom is a luxurious retreat with a comfy king-sized bed, a flat-screen TV, a large dresser, and an ensuite bathroom. The ensuite bathroom is a spa-like haven, featuring a shower and bathtub combination, a granite vanity, and plush towels. It's the perfect space to rejuvenate after a day of sun and sand. The guest bedroom is equally inviting, offering a queen-sized bed, soft linens, a flat-screen TV, and a spacious closet. The adjacent guest bathroom features a large glassed walk-in shower, a vanity, and quality towels, providing convenience and comfort for your guests.brbrBeyond the condo's allure, the proximity to Siesta Key's main beach access is a game-changer. Picture yourself strolling across the street to enjoy the sugar sand, beach volleyball, outdoor showers, and a charming cafe. For families, the nearby playground adds an extra layer of convenience.brbrThis vacation rental is not just a place to stay; it's an experience. Immerse yourself in luxury, soak in the natural beauty, and create lasting memories in this impeccably updated condo. Your Siesta Key getaway starts here!brbrOur House at the Beach CondosbrWelcome to Our House at the Beach, a premier condo complex offering the perfect blend of luxury and convenience for your vacation retreat. Nestled just across the street from Siesta Beach, ranked as the number 1 beach in the United States, this condominium promises an unparalleled beachside experience.brbrOur House at the Beach boasts a range of amenities to enhance your stay, including two tennis courts and a heated pool, perfect for relaxation and recreation. Each vacation home is equipped with fully furnished kitchens, ensuring a seamless and enjoyable culinary experience. The spacious balconies offer a tranquil setting to unwind, while covered parking provides added convenience.brbrFor entertainment, enjoy cable TV and free WiFi available in all rooms and the pool area. Fire up the gas grill for a delightful barbecue experience. As you step outside, the pristine Siesta Beach awaits, offering lifeguard protection, showers, bathrooms, snack bars, grills, picnic tables, shade trees, and ample parking.brbrExperience the ultimate beachside getaway at Our House at the Beach, where comfort and luxury harmonize with the natural beauty of Siesta Beach.brbrThe Beauty of Siesta KeybrSiesta Key is a barrier island positioned between the Gulf of Mexico and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids. brbrThe Siesta Key Village offers a wide selection of shops, cafes, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate.
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Exceptional(29)

$1308.45

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Private Vacation Home

Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!

Siesta Key, Florida, United States

Island Escape | Heated Saltwater Pool + 2 Min Walk to Siesta Beachbrbr Why You'll Love This HomebrStep into Island Escape, where freshly completed renovations meet the charm of Siesta Key's coastal lifestyle. With a heated saltwater pool, gourmet indoor and outdoor kitchens, and two spacious balconies, this single-family retreat blends modern luxury with island ease—just steps from the powder-soft sands of Siesta Key Beach.brbr ‍ ‍ Perfect ForbrFamilies, friend groups, and beach lovers seeking an upscale, walk-to-everything home with indoor/outdoor living and private resort-style amenities.brbr Imagine ThisbrWake up to gentle Gulf breezes, brew coffee in the sunlit kitchen, then step onto your balcony for a poolside view. Spend the morning at the beach—only a 2-minute stroll away—before returning for a grill-side lunch in the shaded outdoor kitchen. Cool off in the heated pool, lounge in the cabana room for ping pong or TV time, then gather on the balcony for sunset. Evenings are for strolling to Siesta Key Village's shops and dining, just 0.7 miles away.brbr Where You ll Sleepbr• Bedroom 1 – Main Level: Queen Bed, Adjacent Half Bath, TVbr• Bedroom 2 – Upper Level (Primary): King Bed, Ensuite Bath, TVbr• Bedroom 3 – Upper Level: King Bed, Shares Hall Bath, TVbr• Bedroom 4 – Upper Level: Two Queen Beds, Shares Hall Bath, TVbr• Living Room: Queen Sleeper Sofabrbr Explore the Areabr• 0.1 Miles / 2-Minute Walk to Siesta Key Beachbr• 0.7 Miles to Siesta Key Village for Dining, Shops, and Nightlifebr• Easy Access to Water Sports, Fishing Charters, and Coastal Parksbrbr⌛ Don't Miss Out - This home books quickly—your stay includes our CottageClean™ program: a 6-hour deep clean and 35-point inspection so you arrive to a home that feels brand new. brbrNeed To Know - The pool is heated from November 15th to April 15th. There are stairs in this home leading to the upstairs bedroom; if any guest has difficulty with stairs, please contact us for alternative accommodations. Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights.
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Bath 2

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Sleep 12

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$386.65

/ Nightly
Condo

Siesta Key Direct Bay view 2-bedroom condo

Siesta Key, Florida, United States

Discover the beauty of Siesta Key from this 2-bedroom Bayfront condo in Peppertree Bay, a Gulf to Bay complex. Complex includes two pools, fitness center, and tennis / pickleball courts. Look for dolphins while enjoying your coffee from the enclosed lanai. Spend your afternoon casting from the fishing pier steps away from your unit or relaxing at one of the two pools in the complex. Keep up with your fitness routine in the on-site workout space. Or stroll across the street to the gulf and enjoy private beach access. The unit comfortably accommodates up to 4 guests, with a king bed in the primary bedroom and premium sofa bed in the second bedroom. The second bedroom includes a desk and can also be used as a den / office. Each of the bedrooms has a smart tv and wifi hi speed internet.br The kitchen is fully outfitted with everything you need for a homemade meal and a has a pass through to the living area. The dining area is open to the living area, with a table that seats 4. The living area has ample seating, with a couch and love seat and panoramic views of the intracoastal. It also includes as well as a TV and Bose Wave radio. The enclosed lanai has floor to ceiling windows and a cafe table where you can enjoy your morning coffee. Unit includes washer and dryer and dedicated parking spot at the base of the entry stairs.This is a second floor unit and requires a flight of exterior stairs to access.brbrWhether you’re unwinding indoors or exploring nearby, this enchanting condo offers everything you need to enjoy your stay in paradise. We look forward to hosting you at the Waterfront.br* Property Amenitiesbr* 2nd floorbr* 2 BD Garden Villasbr* Air Conditioningbr* Bay Sidebr* Coffee Makerbr* Cooking Basics - Pots & Pans, Salt & Pepperbr* Dining Tablebr* Dishes/ Utensilsbr* Essential Starter Suppliesbr* Exercise Facilitybr* Fire Extinguisherbr* Full Kitchenbr* Hair Dryerbr* Heatingbr* Internet Accessbr* Iron/Ironing Boardbr* Non-Smoking Unitbr* Refrigerator/Freezerbr* Smoke Detectorbr* Stove/Ovenbr* Toasterbr* Towels and Bed Sheetsbr* TV Cable/Satellitebr* Washer/Dryer
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Sleep 4

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Exceptional(96)

$465.72

/ Nightly
Condo

Prime Beachfront with Views, Views, Views!

Siesta Key, Florida, United States

You can't get much closer to the water than this! STEPS to the sand with stunning Siesta Beach views from every room. The Gulf seems to surround you from this gorgeous, completely remodeled 4th floor 2BD 2BA unit. Just a short ride down the elevator from the 4th floor and you're on the sand!brbrThe unit also overlooks the heated Beachfront Pool! brbrCoastal Chic can be used to describe the completely remodeled Beachfront unit. Attention to detail is apparent as you enter to find an open concept Living/Dining/Kitchen area with Gulf views all around! The Living area opens to a private, oversized L shaped balcony/patio perfect for enjoying the sunsets, and fabulous Siesta Beach views. brbrThe Master bedroom has two Queen beds, a large closet, and also opens to the private balcony with Siesta Beach views. The Guest bedroom has two Full size beds and a walk-in closet. Both baths are completely remodeled. Convenient washer and dryer IN unit. The unit has two Flat Screen TV's - a 58 in the living area and a 43 in the master bedroom. brbrBeach towels, and a medium size cooler is provided. The complex provides beach chairs and lounges at the beach. The unit features high speed, fiber-optic Wi-Fi with a dedicated router providing a secure connection. High speed Wi-Fi is also available throughout the property, with full coverage on the beach and down to the water! brbrThe dedicated parking spot is located directly beside the building providing very easy access to the unit. The oversized parking spot easily accommodates vehicles such as large SUV's or Minivans.brbrThe condo has satellite TV with over 200 channels. Enjoy easy access to the beachside grilling pavilion directly beside the building.brbrIf they gave awards for sand - well, they do.....brStephen Leatherman, known as Dr. Beach, says I use 50 criteria to rate every beach, and in terms of sand alone Siesta Key is definitely the best in the world.brbr#1 Best Beach in the US - Trip Advisor 2025br#4 Best Beach in the World - Trip Advisor 2025br#1 Best Beach in FL - US New & World Report 2025br#1 Best US Beach - US News & World Report 2024br#1 Best Beach in FL - U.S. News & World Report 2024br#1 Best Beach in FL - Trip Advisor 2024brOne of the Worlds Most Beautiful Beaches - U.S. News & World Report 2024br#2 Best Beach in the US & #14 in the World - Trip Advisor 2022br#1 Best Beach in the US & #11 in the World - Trip Advisor 2020br#1 Best Beach in the US - Dr. Beach 2017 and 2011br#2 Best Beach in the US - Forbes 2019br#1 Place to Live in Florida - US News & World RPT 2019br#3 Place to Retire in US - US News & World RPT 2019br#1 Best Beach in the US - TripAdvisor 2017 br#1 Best Coastal Place to Live in FL - Coastal Living Magazine 2017br#2 Best Beach in the US - Dr. Beach 2016br#1 Beach in the World - AARP 2015 br#1 Beach in the US - Trip Advisor 2015, 2014, 2013brFamily Beach Award' - Family Vacation Critic 2013 brTop Ten Beaches in the World - National Geographic 2011brBest Beach in the State of Florida- Florida Trend Magazine 2010brBest Sand Beach on the Planet - Travel Channel 2004 br brJamaica Royale provides 3 heated, freshwater pools, two beach Tiki Huts, chairs and lounges for the beach, as well as lovely tropical, manicured lawns and grounds. There is friendly and helpful on site property management, full time housekeeping, grounds maintenance, and security staff. The condo has an e-lock system so no need to keep up with keys. A unique code is generated to unlock the door for each guests stay. Enjoy easy check-in from the on-site office located in front of the complex.brbrIt's just one mile from the condo to popular Siesta Key Village where you'll find a wide variety of restaurants, shops, and nightlife. Everything from Zagat rated restaurants to very casual dining options exist on the Key. Free shuttles run throughout the day and night to Siesta Key Village. It's also just a short drive (15 mins) to mainland Sarasota where you can enjoy world class museums and cultural opportunities, as well as additional dining and shopping areas. brbrBe our guest and enjoy a stay in this beautiful beachfront unit on Siesta Key!
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Bath 2

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Sleep 6

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