Home Vacation Condo Rentals By Owner In Siesta Key, FL

Showing 100 Of 1244 Vacation Rentals
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Exceptional(2)

$249.06

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Sun, Sand, and Relaxation! - Aloha Kai #43 - Roelens

Siesta Key, Florida, United States

Aloha Kai #43brbrTime for Some Beach Time!br brEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #43. This charming beach villa is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Fresh and inviting with colorful coastal comfort, Aloha Kai #43 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special: br brBedding Arrangement: br1 Bedroom: brMaster Suite: King-size bed and Smart TV brAdditional Sleep: Queen-size sleep sofa in the living areabrTop Features: brSleeps 4 brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation. brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort. brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun. brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #43 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this villa offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #43 today and create memories that will last a lifetime! brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future! brbrDISCLAIMERS: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.
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Sleep 4

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Exceptional(15)

$337.56

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Siesta Key Condo: Beach, Pool & Village Fun!

Siesta Key, Florida, United States

Summary:brbrEscape to paradise in our newly renovated 2-bedroom condo, perfectly situated a block from Siesta Key Village. Enjoy the convenience of walking to bars and restaurants, plus two parking spots if you prefer to drive. Relax by the community heated pool or take an 8-minute stroll to the award-winning beach. Explore the area using the free trolley, or venture to downtown Sarasota. This dog-friendly condo offers Wi-Fi, a smart TV, in-unit laundry, and essential home and beach gear.brbrbrbrThe Space:brbrStep inside this beautifully renovated condo and discover a comfortable and inviting space designed for relaxation and enjoyment. The condo features two well-appointed bedrooms, a full bathroom, and a bright, open-plan living area. The Master Bedroom boasts a luxurious King bed, ensuring a restful night's sleep, and offers ample closet space. The Second Bedroom provides a cozy retreat with a Queen bed, perfect for guests or family. The Full Bathroom is thoughtfully designed, providing all the necessary amenities. The living area is the heart of the home, offering a comfortable space to unwind after a day at the beach or exploring Siesta Key Village. The fully equipped kitchen allows you to prepare meals with ease, while the dining area provides a perfect setting for enjoying them. Step outside onto the patio or balcony to enjoy the Florida sunshine and fresh air.brbrbrbrGuest Access:brbrGuests will have full access to the entire condo, including the two bedrooms, the full bathroom, the living area, the fully equipped kitchen, and the patio. Enjoy the convenience of in-unit laundry. You'll also have access to the community's heated swimming pool, perfect for a refreshing dip. Please note that this is a dog-friendly condo, and any pets must be approved beforehand. Parking is available with two parking spots. The condo is a short walk from Siesta Key Village and an 8-minute stroll to the beach.brbrbrbrThe Neighborhood:brbrStep outside and immerse yourself in the vibrant heart of Siesta Key! Our condo is perfectly positioned for you to experience the best of the island. Just a block away, Siesta Key Village buzzes with energy. You'll find a fantastic selection of restaurants, bars, and shops, all within easy walking distance. Indulge in fresh seafood, enjoy live music, or browse unique boutiques – the village offers something for everyone. For beach lovers, the world-famous Siesta Key Beach is just an 8-minute stroll away. Sink your toes into the powdery white sand and bask in the sun. If you're looking to explore beyond the village and beach, the free Siesta Key trolley provides convenient access to various island locations. Plus, downtown Sarasota is easily accessible, offering a broader range of cultural and entertainment options.brbrbrbrGetting Around:brbrGetting around Siesta Key and beyond is a breeze! Our condo offers two convenient parking spots for your use, perfect for exploring at your own pace. For those who prefer public transport, the free Siesta Key Trolley provides easy access to various island destinations, including Siesta Key Village and the beach. If you're arriving by air, Sarasota Bradenton International Airport (SRQ) is approximately a 30-minute drive away. Consider ride-sharing services or taxis for convenient transport to and from the airport. From the condo, you can easily walk to Siesta Key Village for dining and entertainment, and a short 8-minute stroll will take you to the stunning Siesta Key Beach. Downtown Sarasota, with its cultural attractions and diverse dining options, is also accessible via car or public transit. Enjoy the freedom to explore all that this beautiful area has to offer!brbrbrbrOther Things to Note:brbrPlease take note of the following details to ensure a smooth and enjoyable stay at our Siesta Key condo. Check-in time is at 3:00 PM, and check-out time is at 10:00 AM. We kindly request that you adhere to these times to allow our cleaning crew ample time to prepare the condo for the next guests. For parking, you'll have two designated spots available. This is a dog-friendly property, but please note that all pets must be pre-approved, and a pet fee may apply. We also ask that you be respectful of quiet hours, observed between 10:00 PM and 8:00 AM. Parties and events are strictly prohibited. Smoking is not permitted inside the condo or in any of the common areas. We want you to have a wonderful time, so please feel free to reach out if you have any questions!brbrbrbrInteraction with Guests:brbrI'm dedicated to ensuring you have a fantastic stay! I'm generally available to assist with any questions or needs you may have. The best way to reach me is via the platform messaging system, where I aim to respond within an hour during reasonable hours (8 AM to 10 PM). For urgent matters, feel free to send a message, and I'll do my best to assist promptly. I'm here to help make your Siesta Key vacation memorable!
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Exceptional(33)

$222.15

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Walk to Siesta Key Beach, 2 Heated Pools, Baby Pool, Tennis Courts, Fishing Piers, Updated Condo

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Harbor Towers Gulf Luxe Escape! brbr brbrHarbor Towers Yacht and Racquet Club is a premier complex with loads of amenities that sits directly on the bay, overlooking the intracoastal waterway, where you can watch incredible morning sunrises. Close to famous Siesta Key beach (2 min. drive/15 min. walk) with its fabulous powdery white sands is just a short bike ride or Trolley ride away. Harbor Towers offers resort style amenities including 2 heated swimming pools, 3 clay tennis courts, and clubhouse with grilling station, exercise facility and sauna. brbr brbrLOCATION HIGHLIGHTS: brbr- Directly on the bay with intracoastal waterway views brbr- 2 min drive / 15 min walk to Siesta Key Beach brbr- Close to bike paths and trolley access brbr- Quiet, resort-style setting brbr brbrPROPERTY FEATURES: brbr- 3 bedroom/ 3 bathroom corner unit on the 3rd floor (1755 sq ft) brbr- Resort-style amenities: 2 heated swimming pools, 3 clay tennis courts, clubhouse with grilling station, exercise facility, and sauna brbr- 1 assigned parking spot brbr- Private washer and dryer combo, communal laundry room on each floor brbr- Dedicated WIFI and cable brbr brbrLIVING ROOM: brbr- L-shaped couch with access to the enclosed balcony brbr- Entertainment-ready with TV and cable brbr- Den room with queen sleeper sofa and TV brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen (appliances, cookware, dishes included) brbr- Dining space connected to living area brbr- Dining table seats 6 plus 4 more at the breakfast bar brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, TV with cable, closet space brbr- Master ensuite bathroom: separate vanity area, walk-in shower brbr- Guest bedroom #1: queen bed, view of the front of the complex, closet space brbr- Guest bathroom: vanity with tub/shower combo brbr- Guest bedroom #2: two twin beds, access via sliders to enclosed balcony brbr- Guest ensuite bathroom: vanity with tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. brbr brbrLOCAL FAVORITES: brbr- Famous Siesta Key Beach brbr- Nearby bike paths and trolley stops brbr- Local restaurants and shops a short ride away brbr brbrIMPORTANT INFO: brbr- Only 1 parking spot. Parking restrictions: no trailers, oversized vehicles, boats, or commercial vehicles. No Motorized Carts or Scooters Allowed brbr- No smoking, no pets brbr brbrYOUR ULTIMATE BEACH VACATION STARTS HERE. BOOK YOUR STAY AND START UNWINDING THE MOMENT YOU ARRIVE!brbrPlease note, each unit is only allowed 1 parking spot. brbr brbrStarting June 1st, the complex has scheduled a roof repair. They are expecting to be done in 4-5 weeks (weather permitting). brbrCrane will be up front. Carport repairs will take place starting June 8, 2026. Please use caution around work areas. Thanks for your understanding.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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Bath 3

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Sleep 7

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Exceptional(4)

$197.88

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Walk to Beach | Water View | Heated Pool plus Heated Baby Pool | Clay Tennis Courts

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Harbor Towers 3rd Fl 2 Bedroom! brbr brbrNewly furnished, new pics to come! brbr brbrEnjoy this condo that offers stunning bay views with incredible morning sunrises! Just a short drive, walk, or bike ride from Siesta Beach, its perfect for beach lovers. Enjoy resort-style amenities with the comfort of a cozy unit. brbr brbrLOCATION HIGHLIGHTS: brbr- Direct bayfront setting on the Intracoastal brbr- Quick 2–3 minute drive or 15-minute walk to Siesta Key Beach brbr- Trolley stop just outside the building brbr- Close to Siesta Key Village dining, shopping, and live music brbr- Resort-style community with marina views and sunrise scenery brbr- 2 heated swimming pools, 3 clay tennis courts brbr- Clubhouse with grilling station, exercise facility, and sauna brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2 bathroom 3rd floor condo (1152 sq ft) brbr- Dedicated WIFI and cable brbr- Central AC with ceiling fans brbr- Screened-in balcony brbr- 1 assigned parking spot brbr- No area rugs brbr brbrLIVING ROOM: brbr- Comfy couch that doubles as a sofa bed brbr- Wall-mounted TV with cable brbr- Access via sliders to screened balcony brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with stainless steel appliances and double sinks brbr- Dining table seats 4 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, TV with cable, door access to balcony brbr- Master ensuite bathroom: spacious vanity with tub/shower combo brbr- Guest bedroom: queen bed, TV with cable, single twin rollout bed available upon request brbr- Guest bathroom: tub/shower combo brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach umbrella, and beach towels. brbr brbrLOCAL FAVORITES: brbrSiesta Key Beach with powder-white sand and turquoise water brbrSiesta Key Village restaurants, bars, and boutique shops brbrTrolley rides to the beach and village hotspots brbr brbrIMPORTANT INFO: brbr- Quiet hours enforced by the community brbr- No parties or smoking allowed. No pets brbr- Only 1 parking spot. Parking restrictions: no trailers, oversized vehicles, boats, or commercial vehicles. No Motorized Carts or Scooters Allowed brbr brbrRELAX, UNWIND, AND LET YOUR PERFECT VACATION BEGIN - SECURE YOUR STAY TODAY!brbrPlease note, each unit is only allowed 1 parking spot. brbr brbrStarting June 1st, the complex has scheduled a roof repair. They are expecting to be done in 4-5 weeks (weather permitting). brbrCrane will be up front. Carport repairs will take place starting June 8, 2026. Please use caution around work areas. Thanks for your understanding.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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Bath 2

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Sleep 5

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Exceptional(159)

$344.26

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Spectacular Beach View! Right on Beach! Amazing views!!

Siesta Key, Florida, United States

** BEACH FRONT WITH VIEWS** We did not get any damage to condo!!! December dates available at great rates!!! Complex did a great job cleaning up!! We are ready to rent Nov. 1st. come visit, you will not be disappointed!!brbr***Located Directly on Siesta Key Crescent Beach with White Sugary Sand***brJust a few steps and you are directly on the beach with free beach and lounge chairs.brbrBeach Gulf view from all rooms!!! Enjoy your morning coffee while looking at the beach and blue water with a delightful breeze, no better way to start your day!brbr This 5th floor two bedroom, two bath condo is totally and completely renovated. New tile throughout. There are two bedroom suites with private baths. It is a split floor plan so each suite is on different sides of condo for privacy. Each bedroom has new slider doors that open to screened in lanai with beautiful Gulf Views. Both rooms also has new furniture, mattresses and flat screen t.v.'s. Each bathroom is completely renovated with brand new walk in shower, new vanity, toilet, lighting. paint, ect. brOne bedroom has a King bed and 2nd bedroom has two queen beds to sleep 6 comfortably. brKitchen is brand new with new cabinets, granite counter tops and appliances. The kitchen is also completely stocked with everything that the cook might need to make your stay comfortable. All new cookware, glasses, flatware ect.brLiving room has beautiful new slider doors that open to lanai. Living room also new furniture, 55 flat screen t.v. with cable, and free wifi. brAll rooms have new ceiling fans, paint and new molding. brCondo is only a few steps to the #1 beach. Walk out of the building and put your feet in the white sugary sand of beautiful Siesta Key beach. Beach lounge chairs are supplied free of charge right in front of condo.brbrThere is also a very reasonable service at beach entrance where you can have umbrellas and chairs set up for you and ready for whenever you go to the beach.brbrGorgeous Gulf views from both bedrooms and living room. Lay in bed and open your eyes to a beautiful beach, blue water of the Gulf of Mexico!brbr Crescent Arms offers a picturesque pool that is secluded for your privacy and heated in winter for your comfort. The clubhouse, restrooms and showers are at the pool for your convenience. It is also a gated community and has one assigned parking spot with carport and visitor parking for extra cars. brbrClose to restaurants, stores, shopping, ice cream ect. A perfect place to spend a great vacation. Close walking distance to market, ice cream, restaurants, cafe, 7-11, tiki bar, Daiquiri Deck, famous Cap't Curts seafood. ect. brbrThere are also free jitneys and Trolley that will take you the length of the Key.brbrVery close to The Point of Rocks where people love to search for shells and go snorkeling. A perfect stay on this more private peaceful part of Famous Siesta Key Beach.brbrbr
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$336.62

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Gulf and Bay Club - A704

Siesta Key, Florida, United States

Gulf and Bay Club Unit A704 Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit A704, a bright and inviting two bedroom, two bathroom condo located in one of Siesta Key’s most sought-after beachfront communities. Perfect for extended stays, this 28-night minimum retreat places guests just a 5-minute walk from world-famous Siesta Beach, known for its powder-soft quartz sand and turquoise waters. With spacious interiors, serene paths, and an impressive collection of resort-style amenities, this condo is ideal for snowbirds, couples, or small families seeking comfort, convenience, and an elevated Siesta Key experience.brbrHighlightsbr• 5-minute walk to Siesta Beachbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 1 Queenbr• Washer and dryer in unitbr• One assigned parking spotbr• Access to multiple shared poolsbr• Shared fitness center and spabr• Shared tennis and pickleball courtsbr• Gulf and Bay Club gated communitybrbrGuests at Gulf and Bay Club enjoy an exceptional lineup of resort-style community amenities designed to enhance long-term stays. Spend your afternoons relaxing by one of the heated shared pools, unwind in the shared in-ground spa, or enjoy a rejuvenating session at the fitness center. Active travelers will love the tennis courts, pickleball courts, and shuffleboard, while the shared cornhole area and clubhouse offer plenty of space for socializing. Beautifully maintained grounds, walking paths, and tropical landscaping create a peaceful atmosphere throughout your stay.brbrInside Unit A704, the open living area offers comfortable seating and large windows that fill the space with natural light. The fully equipped kitchen includes a refrigerator, stove, oven, dishwasher, microwave, toaster, and drip coffeemaker, making meal preparation simple and convenient. Enjoy casual breakfasts at the kitchen bar or gather at the dining table for relaxed evenings at home.brbrThe primary bedroom features a plush king bed, ample storage, and an ensuite bathroom, creating a private retreat after days spent exploring Siesta Key. The second bedroom offers a cozy queen bed and easy access to the shared hallway bathroom, making it perfect for visiting family or friends. Both bedrooms are designed for extended comfort with soothing coastal colors and space to settle in.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroombr• Second Bedroom: Queen bed, hallway bathroombrbrEnjoy the convenience of an in-unit washer and dryer, ideal for longer stays. The condo’s central Siesta Key location places guests close to Siesta Key Village, where you can enjoy waterfront dining, boutique shopping, coffee bars, and live entertainment. Whether you prefer relaxing beach days or exploring Sarasota’s arts and cultural scene, this home serves as a perfect home base.brbrWith its unbeatable location near Siesta Beach, comfortable two bedroom layout, and access to Gulf and Bay Club’s outstanding amenities, Gulf and Bay Club Unit A704 is the ideal Siesta Key escape for extended stays. Book your stay with Tropical Sands Accommodations and enjoy the coastal Florida lifestyle at its finest.
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Exceptional(7)

$436.95

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Siesta Key Beachfront - 2BR Condo w/ Pools & Views

Siesta Key, Florida, United States

Welcome to Jamaica Royale #203 – Beachside Comfort with a ViewbrSiesta Key, Florida | 2 Bed · 2 Bath · Sleeps 6brbrPerched on the second floor of Tower II in the exclusive, gated Jamaica Royale community, Unit #203 offers the perfect blend of coastal comfort and resort-style amenities—just steps from the world-renowned sands of Siesta Key Beach.brbrThis bright and inviting 2-bedroom, 2-bathroom condo features a king bed in the primary suite and two full beds in the second bedroom, ideal for families or couples traveling together. Enjoy beach views from your private lanai and relax with high-quality linens, bedding, and towels that ensure a restful stay.brbrThe fully stocked kitchen has everything you need for home-cooked meals, from morning coffee to seafood dinners. Step outside to find two large community pools, shared BBQ grills, and direct beach access complete with chairs, loungers, and umbrellas—both from the community and additional beach amenities provided in the unit.brbrOther conveniences include:brbrShared coin-operated laundry facilitiesbrSecure, gated complexbrPrivate beach area and lounge spacesbrDedicated Wi-Fi and streaming-ready TVsbrbrWhether you're looking for a week of sun-soaked relaxation or a work-from-beach getaway, Jamaica Royale #203 is your perfect island escape.brbrLocation Highlights:brJust minutes to Siesta Key Village, restaurants, shops, and watersport rentals.brbrWhat's provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner. brbrBook now and enjoy one of the best beachfront values on Siesta Key!
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$447.15

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Spacious beachfront Penthouse 3 bed/3 bath suite, Stunning Gulf views!

Siesta Key, Florida, United States

Location Location!! Spectacular views of the beach and water from our 5th-floor Penthouse condo suite with 3 King beds and new mattresses. Remodeled baths. Each day, enjoy our Magical Sunsets! The open floor plan is spacious and perfect for entertaining. The Living Room has plenty of seating. Beautifully decorated with a Leather sofa, love seat, Recliners, and a 75 Smart TV.brThis spacious and bright unit has a Renovated Kitchen with granite counters, a Microwave, and Stainless Steel Appliances. Staying calm and comfortable is easy, thanks to our unit's central air conditioning and ceiling fans in every room.brThe Main Bedroom suite features a king-size bed with a new comfort-top mattress, a Flat-Screen TV, a walk-in closet, and a remodeled bathroom. Imagine relaxing in bed, enjoying a view of the white-sand beach and the clear, sparkling waters of the Gulf of America. This is not a dream. It just feels like one!brBoth Guest suites have king-sized beds with new comfort mattresses, flat-screen TVs, and a private bathroom.br Amenities include a private gated beach, lounge chairs, a New Tiki Hut with Gas grills, tables, chairs, a lounge area—a picnic area with charcoal grills—and a heated pool with restrooms.brThe elevators are located in the middle of the building. Carts for carrying luggage are on the ground level next to the elevators. Coin-operated laundry is on each level by the elevators. There is assigned parking on the bottom level, with additional parking for guests with a permit from the office. brYou can't beat the location! Across the street from restaurants, ice cream, grocery stores, drug stores, pizza, a bakery, beach gear rentals, the post office, and 7-11...brWalk out your door onto the beach- no shoes needed! Warm crystal waters, tropical breezes, and the most inspiring sunsets await you in Siesta Key. So come to Siesta Key, calm your mind, and soothe your soul in paradise!
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Exceptional(2)

$332.67

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Updated 2BR Siesta Key condo with beach access - GBB1269

Siesta Key, Florida, United States

Welcome to your ideal vacation destination on Siesta Key. Professionally managed by Gulf Coast Vacation Rentals, this beautifully updated two-bedroom condo is conveniently located near the pool, tennis courts. Recently introduced to our rental program, be among our first guests and enjoy an unforgettable stay!brbrFrom the moment you arrive at Gulf & Bay Club Bayside, you'll be enchanted by the beauty, serenity, and charm of this Key West style village. Situated on the bay, just across the street from the world-famous Siesta Key Beach, our location offers exquisite views of the Intracoastal Waterway. You'll be greeted by balmy breezes and have the delightful opportunity to observe local birds, fish, and even manatees.brbrOur spacious unit, individually owned and decorated, is surrounded by lush, tropical landscaping, shell paths, and tranquil lakes with soothing fountains. The layout of our condo provides a sense of privacy and individuality. You can relax in air-conditioned comfort or open the windows to invite in the refreshing gulf air.brbrThis charming condo offers two heated pools, two tennis courts (which can also be used for pickleball), and an exercise room, providing ample on-site activities. BBQ grills, a fishing dock, and picnic areas are available for all guests to enjoy. For your convenience, the condo includes a private garage and a washer and dryer in the unit.brbrThe highlight of your stay will be the deeded walking access that allows you to easily walk across the street and down a path to the beautiful Siesta Key or Crescent Beach. Siesta Key Village, just a short distance away, offers dining, shopping, and entertainment.brbrHouse Rules: No Motorcycles, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.
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Bath 2

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Exceptional(4)

$328.07

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Beach Access, 2 Pools and Fishing Dock - GBB 1260

Siesta Key, Florida, United States

Discover relaxation in this spacious ground floor two-bedroom, two-bath home with an attached garage, professionally managed by Gulf Coast Vacation Rentals. Unwind on the private south-facing lanai that overlooks a serene lake adorned with a fountain, often frequented by delightful water birds. After a day of adventures, enjoy HDTV and high-speed internet, perfect for streaming your favorite shows. Wireless internet is available throughout Bayside and at the pools for your convenience.brbrThe living area features tiled flooring, while newly-installed plank flooring enhances the comfort of the bedrooms. Updated bathrooms, in-suite laundry, and a well-equipped kitchen with stainless steel appliances ensure your stay is filled with all the comforts of home.brbrJust a short walk away awaits Crescent and Siesta Beach, renowned as the No. 1 beach in the US, with easy access to its famous white sands and crystal-clear blue waters. Conveniently situated midway between two pools on the Bayside grounds, guests also have access to a newly renovated fitness center, gas BBQ grills, and tennis courts. A charming fishing dock along the shell-lined walking path surrounding the property features a fish light, attracting a diverse array of marine life for added enjoyment.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets
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Exceptional(5)

$188.94

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Walk to #1 Siesta Beach, 2 Bedroom, 2 Baths, Heated Pool, Wifi, Covered Parking.

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, NO PETS.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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$137.16

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~ Stay 2 Weeks for the Price of 1 at Harbor Towers ~ Aug 18 to Sep 19

Siesta Key, Florida, United States

** Stay 2 Weeks for the Price of 1 at Harbor Towers ** Aug 18 to Sep 19brbrWelcome to the prestigious Harbor Towers and Yacht Club on Siesta Key.brbrThis apartment/condo is located on the second floor, with convenient, easy access to the stairs.brbrNO NEED to take the elevator.brbrIt’s a nice option in these times of social distancing, which decreases crowd contact,brand an added safety option.brbrWalk the property and find your favorite spot to take in the beautifully landscaped and lush tropical setting. Walk to the gazebo, and see the twinkling lights of Sarasota or the boats and yachts in the distance. Breathe deep and take in the sweet smell of occasional jasmine, and admire the tropical flowers along the pathways.brbrYour 2-bedroom apartment is spacious, accommodates 6, and is decorated in soft tropical colors. Enjoy the wonderful, calming views of the marina and bay as you have your morning coffee and breakfast from your enclosed patio.brbrThe apartment has tile throughout.brStay on the premises after you have explored all the beaches: br10-minute walk to Siesta Beach, the #1 rated beach in the United States (as if you didn't know that already, after all, isn't that why you want to come and visit ), or go for a short drive to Turtle Beach and have your lunch in town and enjoy the safety and beauty of Harbor Towers Yacht and Racket Club:brbrGated entrybrAssigned parkingbr2 little private balconies br2 heated poolsbr3 lit Har Tru (clay) tennis courtsbrBBQ areabrKayak LaunchbrPrivate MarinabrSaunas and the new gymbrbrI am certain you will fall in love with this property and area just as I did, and find it so calming and relaxing having all these amenities right on the premises, and all the action, dining, and entertainment you would want in town.brbrEnjoy!brbrPARKING POLICIES:brDue to limited parking, no boats, wave runners, jet skis, trailers, or RVs are allowed on the property. One parking spot per condo with a permit.brbrThere is a community laundry on each floor by the elevators.br*brNO pets—condominium association and the management rule. brbr*When you reserve it for your use, we will most likely have to turn away other renters wanting to rent during the same period. We need to ensure that you intend to occupy the property during the time interval you are reserving.*brbr*Travel insurance is strongly recommended in Florida.brPreserver provides cancellation and interruption services as well as emergency assistance and travel services. Protect yourself in the event of hurricane evacuations and family emergencies, such as illness or death in the family. We strongly encourage the purchase of independent travel insurance if this is a concern or in the event of an illness or any circumstances beyond your control.*brbrAbout Travel InsurancebrbrTravel insurance is available for purchase when you book and pay through our site. It helps safeguard your trip from delays, interruptions, and cancellations for covered reasons, and you can be reimbursed for the resulting out-of-pocket expenses and non-refundable trip fees. Travel insurance is provided by CSA and underwritten by Generali U.S. Branch.brbrVisit Generali's website to read the Description of Coverage or Policy.brbrBuy travel insurancebrYou have the option to purchase travel insurance when you pay for your booking on our site. You can also select this option from your booking confirmation page, post-booking confirmation emails, or by visiting Generali's online portal.brbrCancel travel insurancebrIf you’re not satisfied, you can cancel coverage within 10 days of purchase and receive a full refund. If the reservation is canceled by the owner, regardless of when coverage was purchased, contact Generali to receive a refund​​​​​​.brbrFile a claimbrYou can file a claim with Generali Travel Protection by filling out a claim form, providing the required documentation, and submitting it to the Generali claims department.br*brEffective immediately, e-bikes, e-scooters, and bikes are prohibited at Harbor Towers in the building or in the apartments based on a memorandum received from our insurance agency. They must be parked at the bike rack at the southeast corner.
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Gulf Front Siesta Key Beach Condo

Siesta Key, Florida, United States

Salt Life Villa is a ground-floor 2 bedroom/2 bathroom condo featuring full panoramic Gulf of Mexico views from the living room & the master bedroom. Your dedicated covered parking space is just 8 steps to your front door, with no stairs to climb! brStep through the front door to the open floorplan featuring a living/dining area with bar, Smart TV, private high-speed WiFi, & full view sliding doors leading to the lanai. The kitchen is upgraded with all the amenities of home. brTwo well-appointed bedrooms with fully private ensuite bathrooms, TV/DVD players, & ceiling fans for comfort. A private washer/dryer is also a nice amenity- no sharing with other guests!brThe beachside, fully furnished screened lanai offers a walk right out the door down our private beach path to the pristine Gulf waters and powdery white sugar sand of the world renowned and #1 rated Siesta Key Beach. There is also a smaller side patio accessed only from the master bedroom with an outside shower right out the door. If you are planning a beachside dinner, our gas BBQ grill is there for your use. brAll beach gear, including chairs, umbrellas, sand toys, beach towels, and a beach cart are provided to make for stress-free days of fun and sun at the beach. brEnjoy our direct Gulf front location in this small, quaint complex of 6 units, which is the perfect retreat away from the crowds. Quiet moments of privacy, the sights and sounds of nature lend to a peaceful setting while enjoying your morning on the private screened-in lanai, or watching late afternoon sunsets; take in the Gulf breeze while hearing the calming sounds of the Gulf. brTake a stroll to Siesta Key Village only a few blocks away, or ride the Siesta Key Breeze trolley, which has a stop directly across the street heading north into the Village, or just steps away for a trip to the South Village area, and Turtle Beach. Both Villages offer an array of shops, restaurants, bars, and souvenir options. The Key also offers water sport rentals for those days out on the water.brWe welcome you to enjoy our home and start making wonderful memories with your family and friends, just like we have been doing for over 25 years of ownership at Salt Life Villa. Come and let your toes revel in the 99% pure quartz Siesta Key sand, which stays cool under your feet even on the hottest days!brbr
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$367.25

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Last minute cancellation! Available March 21-28. discount on rate

Siesta Key, Florida, United States

* BEST BEACH IN THE US ⛱ Siesta Beach was named best beach in the United States with Clearwater Beach coming in 6th. Details: https://bit.ly/4gI6AWp. 2023 Tripadvisor “Best of the Best Beaches” Traveler’s Choice Awards*. *2022 TripAdvisor ranks Siesta Beach #2 in the US( top beach on the mainland) & #14brin the worldbr*2020 Tripadvisor ranks Siesta Beach #1 top beach in the US and #11 in the WORLDbr(based on travelers reviews & ratings) pristine beach that never seems to end.brA place in the sun that warrants returning again and again.brbr*2018 named #2 beach of the 50 most Beautiful Beaches of the Worldbrbr*2017, 2011 named America's Best Beach - based on 50 criteria evaluated by Dr.brBeach Stephen Leathermanbrbr*2017, 2015 named #1Beach in the US and #5 in the World according to TripbrAdvisorTraveler's Choicebrbr*2018 named #1 Beach House destination by Trip Advisor!brbrSpacious, beautifully furnished private townhome steps away from Siesta Beach. Sliding glass doors off 4 of the rooms open out to balconies, 2 overlooking the lake featuring a fountain and marine turtles. Relax in a peaceful setting and watch the sky turn color at sunset. Lovely townhome with all the amenities of home. br brLake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Our Lake House offers central A/C, high-speed WI-FI and spacious balconies, ample closet and storage space, cable TV and garage parking for one car. On 15 acres of beautiful property the development includes a private heated pool, covered pavilion area with a BBQ, a picnic area and tennis courts.brLocated across from pure white sand of Siesta Beach!brbrHouse RulesbrbrCheck-in: 4:00 PMbrCheck-out: 11:00 AMbrNo parties/eventsbrNo smokingbrNo petsbrbrMinimum age of primary renter:26brbrbrbrCancellation Policybrbr100% refund if canceled at least 30 days before arrival date.
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$361.64

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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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$350.74

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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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