Home Vacation Rentals By Owner In Siesta Key, FL

Showing 200 Of 2077 Vacation Rentals
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$284.07

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Apartment

Charming Suite w/ Shared Pool, High-Speed WiFi - Steps to the Beach

Siesta Key, Florida, United States

Parrot Beach Cottages Suite #3brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrParrot Beach Cottages on Siesta Key is mere steps - approximately 150 feet - from the beach and the emerald water, situated just behind the waterfront properties and within walking distance of Siesta Key Village. Suite #3 is ideal for up to two adults and two small children, with one king bedroom, one bathroom, a queen-size sleeper sofa, and a kitchenette in its 350 square feet of living space.brbrThis cozy suite is located on the second floor at Parrot Beach Cottages, up a flight of approximately 12 steps. It's a small and intimate space, so if you're using the sleeper sofa (which has a thin mattress and is really only suitable for small kids), you'll likely want to stow it during the day to maximize the living room. The bathroom is accessed through the bedroom and is snug in size as well, with a single sink, a toilet, and a stand-up shower (but no bathtub). There's a small shared deck outside with two chairs, a community pool, as well as one reserved, off-street parking spot for your ease and convenience.brbrThis suite is mere steps from one of the top white sand beaches in the world. In fact, beach access is so close, you'll hear the waves from home base! This area of the beach is a favorite for sunbathing, swimming, romantic sunset walks, small beach weddings, skim boarding, paddleboarding, kayaking, shore fishing, and much more. Fishermen catch everything from snapper and mackerel to snook and jacks. You'll be within walking distance of a number of businesses that rent all sorts of gear, from kayaks and paddleboards to bikes and video game systems. Due to how close the complex is to the beach, several rental outfitters will bring kayaks, paddleboards, and bikes right to the property and pick them up when you're done!brbrThe suite is also within easy walking distance of Siesta Key Village, where you'll find shops, restaurants, live music, and more. Or, head into town for other local adventures, including the world-renowned Ringling Museum, the Marie Selby Botanical Gardens, Mote Marine, Jungle Gardens, and outdoor shopping and dining on St. Armands Circle.brbrThings to know:brThere are three other suites available to rent at the Parrot Beach Cottages fourplex - Suite #1, Suite #2, and Suite #4brFree high-speed WiFibrSmoke-free propertybrSmall kitchenette (without a dishwasher)br*Bedroom is very small, with only a few feet on each side of the bed, no TV, and a very small closet. The sofabed is recommended for children onlybrThe suite has limited storage (one small closet)brThe shower features grab barsbrSnowbird-friendlybrPlease note that the shared pool is small, about 15 feet by 10 feet and about four to six feet deepbrThe overall property is very small, so there is no extra vehicle or visitor parking. There's also no nearby on-street parking. Guests love the location (truly walking distance to the beach and the village) and the more private feel of the beach, since this is a dead-end road and there is no nearby public parkingbrThere is a new home being built on the lot next door. Construction work is permitted by Sarasota County daily from 7:00am to 7:00pm.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 2.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 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
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Exceptional(10)

$186.93

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Condo

A spacious condo in beautiful Siesta Key, Heated Pool, Tennis, Waterfront Picnic

Siesta Key, Florida, United States

Recently fully renovated and tastefully decorated 2-bedroom 2 bathroom 3rd floor condo in the very desirable island community of Bay Oaks. Bay Oaks offers a heated pool, barbecue grill area, tennis courts, fishing area on the intra-coastal and pool table in the club house. Vacation on beautiful Siesta Key less than a ten-minute walk to the public beach access with provided beach chairs, towels, and cooler... everything you need to enjoy the pristine beach across the street. Located 1/2 mile from Siesta Key South-end Village with shopping, restaurants, and bars. If you are looking for even more selection, Siesta Key Village is also just 2 miles north. brbrStep inside and you will enter the main living area furnished with dining table with seating for 6 and the living room area furnished with comfortable lounge seating with queen sleeper sofa and flat screen TV. The kitchen is fully equipped with 4 piece appliance set among other small kitchen appliance, cookware, and dish-ware. Washer & dryer is located just off the kitchen. Around the corner you will find the guest bedroom and bathroom. The guest bedroom is furnished with queen-size bedroom set and access to walk-in closet and guest bathroom. The guest bathroom is equipped with tub/shower combo. Moving down the hall you find the master suite. The master bedroom is furnished with a king-size bedroom set and access to walk-in closet as well as the en-suite bathroom which is equipped with stall shower and double sink vanity. brbrThere is a handy free island trolley that runs the length of the island when you don't want to drive. You can also give a call to one of the free rides.brbrWhether it be a family vacation or just a romantic couple getting away on holiday or a much-needed vacation, you can't go wrong.brbr​​​​​​​No pets allowed, sorry. No smoking permitted in the condo. One carport is provided with additional guest parking if needed.
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Exceptional(1)

$233.62

/ Nightly
Condo

Siesta Key Condo, Private Beach Access & Water Views - Midnight Cove II 122F

Siesta Key, Florida, United States

Midnight Cove II – 122F by Tropical Sands Accommodations brCondo in Sarasota, Florida brbrDiscover your perfect retreat at Midnight Cove II – 122F, a stylish two-bedroom, one and a half bath condo just a short 10-minute walk from the pristine sands of Crescent Beach. Featuring private beach access and stunning views of the intercoastal waterway, this condo is designed for relaxation and fun. br brHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II is a spectacular bayside condominium complex with private beach access to Crescent Beach on Siesta Key and its world renowned pure white sands and breathtaking sunsets. This complex offers a heated pool, two tennis courts, pickleball, basketball, bike racks, BBQ area with grills and tables, fitness room, and a beautiful observation deck and even private docks available to rent (contact for details). brbrInside, you’ll find an open living space filled with natural light, a fully equipped kitchen with granite countertops, and cozy bedrooms featuring a King bed and twin beds. Additional conveniences include a washer and dryer, plus an extra half bath for guests. brbrBook your stay at Midnight Cove II – 122 today and immerse yourself in the beauty and vibrancy of Siesta Key! Experience private beach access, breathtaking views, and a comfortable home base for your unforgettable escape.
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$233.62

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Condo

Family-Friendly Condo with Private Beach Access & Views! - Midnight Cove II 127F

Siesta Key, Florida, United States

Midnight Cove II – 127F by Tropical Sands Accommodations Condo in Sarasota, Florida brbrWelcome to Midnight Cove II – 127F! This two-bedroom, one-and-a-half-bath condo is the perfect beach escape for families. Enjoy private access to stunning Gulf beaches and explore the charming shops, delicious dining, and vibrant entertainment of Siesta Key.brbrHighlights br• Private Beach Walkwaybr• 10-15 min walk to the beach via private path, plus 0.2 mile to Public Beach Access #12br• Heated community pool (84°F) from November to Maybr• Tennis, pickleball, and basketball courts (equipment available at rental office)br• Fitness Center br• Boat dock rentals available br• Beach chairs in unitbr• Picnic/Grilling Areabr• Bike racks throughout propertybr• CornholebrbrMidnight Cove II offers a fantastic bayside experience with access to Siesta Key Beach’s world-famous white sands and breathtaking sunsets. Families will love the heated pool and the variety of sports courts. Enjoy biking, BBQs, and a fitness center, or relax on the observation deck. For extra fun, consider renting a private dock (contact the office for details). brbrYour second-floor retreat features a welcoming living area with cozy seating, a TV, and a dining table. The fully equipped kitchen includes granite countertops, utensils, and island seating for two. Relax in the unique screened-in balcony, perfect for enjoying drinks while taking in intercoastal waterway views. brbrBoth bedrooms are thoughtfully designed for comfort, with a king bed in the primary suite and two twin beds in the second bedroom, ideal for kids. The main bath features an updated walk-in shower, and additional conveniences include a washer and dryer as well as a half bath. brbrBook your stay at Midnight Cove II – 127 and enjoy the perfect blend of relaxation and family fun in Siesta Key! Don't miss out on your dream beach getaway—reserve today!
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Exceptional(33)

$663.62

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Private Vacation Home

*** FULLY UPDATED *** On the Beach, Walk to Village, Watch the Sunsets from Balcony

Siesta Key, Florida, United States

*** FULLY UPDATED December 2025*** This 3 story unit is a 3 Bedroom / 3.5 Bathroom house with spectacular views from every bedroom and private beach access. The house is located a short 2 minute drive to Siesta Key Village, which has the best dining and shopping options on the island. Although you won't have to go any farther than your own backyard to get to Siesta Beach, the #1 rated beach in the USA. This 99.9% pure quartz white sand beach is why people come from all over the world to Siesta Key.brbrThere is a one car garage on the main floor, and a nice covered private stairway taking you up to the first floor of the unit. When you enter the house you immediately step into the open concept living room. With plenty of seating, a large television, and million dollar ocean views, this is where you'll probably spend most of your time in the house.brbrThe fully equipped kitchen is adjacent to the family room. There is a 2 seat dining table in the kitchen, a screened in balcony right off the kitchen with seating for 2, and a large formal dining table on the other side of the family room with incredible ocean views. With plenty of dining areas, you'll look forward to relaxing and taking in the views while you eat.brbrAt the base of the stairway on the main floor there is a 1/2 bathroom which gives access to those in the kitchen and dining areas. When you go up to the second floor you'll find 2 bedrooms. The Master bedroom with a king size bed, walk in closet, and huge sunroom balcony with sliding glass doors and epic ocean views. The en suite Master bathroom is equipped with a double vanity, shower, and large bathtub. brbrThe second bedroom on this floor has a vaulted ceiling, one twin bed, and one double bed with another covered balcony with views out the front of the house. Just outside this bedroom in the hallway is a full bathroom with shower/tub combination. With your own washer and dyer on this floor doing the laundry is as convenient as possible.brbrAs you go up to the third floor you'll find a huge guest bedroom with one twin bed, and one double bed with even more closet space, another TV, and yet another spectacular view from the balcony looking over Siesta Beach. This bedroom offers another full en suite bathroom for convenience.brbrAnd to make this house even more incredible you've got a private BBQ outside on the ground floor with seating, countertops, and plenty of food prep area. The beach access trail is accessible from here, and an outdoor shower right around the corner make this vacation a great indoor/outdoor living experience.
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Exceptional(35)

$524.66

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Private Vacation Home

Beach Front and Walking Distance to Village

Siesta Key, Florida, United States

This 3 story unit is a 3 Bedroom / 3.5 Bathroom house with spectacular views from every bedroom and private beach access. The house is located a short 2 minute drive to Siesta Key Village, which has the best dining and shopping options on the island. Although you won't have to go any farther than your own backyard to get to Siesta Beach, the #1 rated beach in the USA. This 99.9% pure quartz white sand beach is why people come from all over the world to Siesta Key.brbrThere is a one car garage on the main floor, and a nice covered private stairway taking you up to the first floor of the unit. When you enter the house you immediately step into the open concept living room. With plenty of seating, a large television, and million dollar ocean views, this is where you'll probably spend most of your time in the house.brbrThe fully equipped kitchen is adjacent to the family room. There is a 4 seat dining table in the kitchen, a screened in balcony right off the kitchen with seating for 2, and a large formal dining table on the other side of the family room with incredible ocean views. With plenty of dining areas, you'll look forward to relaxing and taking in the views while you eat.brbrAt the base of the stairway on the main floor there is a 1/2 bathroom which gives access to those in the kitchen and dining areas. When you go up to the second floor you'll find 2 bedrooms. The Master bedroom with a king size bed, walk in closet, and huge sunroom balcony with sliding glass doors and epic ocean views. The en suite Master bathroom is equipped with a double vanity, shower, and large bathtub. brbrThe second bedroom on this floor has a vaulted ceiling, and two twin beds with another covered balcony with views out the front of the house. Just outside this bedroom in the hallway is a full bathroom with shower/tub combination. With your own washer and dyer on this floor doing the laundry is as convenient as possible.brbrAs you go up to the third floor you'll find a huge guest bedroom with 2 Queen beds, more closet space, another TV, and yet another spectacular view from the balcony looking over Siesta Beach. This bedroom offers another full en suite bathroom for convenience.brbrAnd to make this house even more incredible you've got a private BBQ outside on the ground floor with seating, countertops, and plenty of food prep area. The beach access trail is accessible from here, and an outdoor shower right around the corner make this vacation a great indoor/outdoor living experience.
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Exceptional(43)

$720.7

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Private Vacation Home

High Tide - 170 “Siesta Key”

Siesta Key, Florida, United States

KEEP READING BELOW. THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME. THERE IS VERY USEFUL INFORMATION THAT YOU WON’T WANT TO MISS!!brbrPremier local manager, Destination Paradise welcomes you to “High Tide”… a cozy 5 bedroom 4 bath vacation home with an awesome outdoor lounge area! This ranch style home sleeps up to 11. It is located in the heart of Siesta Key and is just minutes from world famous Siesta Key Beach and Siesta Key Village.brbr“High Tide” is less than 500 yards to secluded Shell Beach! When you don’t have your toes buried in the fine white sand sun bathing with friends and family, relax on the large private pool patio. Plenty of room for everyone to relax under the lush tropical palm landscape or take a swim into the heated pool and spa. Kick back in the evenings around the propane fire-pit and enjoy cooking on the grill. This home features 3 master bedrooms with attached full bathrooms. Both of which have direct access to outdoor patio. A fourth bedroom has a private outdoor sitting area accessed through a sliding glass door. All bedrooms (except bunk bed room) are fitted with large smart TVs. Have fun cooking and eating in the updated kitchen with plenty of space for everyone. The kitchen is stocked with all the tools needed to prepare a gourmet meal. Wake up with a hot cup of coffee brewed from the combo coffee maker. Enjoy your coffee and breakfast sitting at the outdoor dining table while you admire the morning sun shine through the Florida palm trees. Your paradise is closer than you think, we look forward to having you as a guest.brbrwww.vacationDP .(c o m)brbr“High Tide” can accommodate up to 10 guests with a bedding configuration as follows:br• Bedroom #1, King Bed (1) - Sleeps: 2br• Bedroom #2, King Bed (1) - Sleeps: 2br• Bedroom #3, Queen Bed (1) - Sleeps: 2br• Bedroom #4, Bunk/Trundle Bed (2) - Sleeps: 2br• Bedroom #5, King Bed (1) - Sleeps 2brbrbr***PLEASE NOTE***brbrCOFFEE MAKER: Combo Coffee maker (both drip and K-cups)brbrPOOL HEATER RULES:brPool heat temp is set at 83º and runs each day from 7 AM until 7 PM from October 15-April 15. Outside of these dates, the Florida weather should naturally heat the pool. Pool temps are not guaranteed. This pool is heated by a heat pump and is only capable of heating to around 20-25 degrees warmer than the ambient temperature. (If the high for the day is 55, the pool may only be able to reach 75).brThe spa has a timer of 3 hours, once turned on and can be run at any time and will heat to 100ºbrbrPET POLICY: This home has a $20/pet/day fee. Aggressive/Large breeds (ie. pitbulls, etc) will need to be approved by management prior to your stay. Unclaimed pets will result in a minimum fine of $500/pet. By making this reservation, you agree to this policy. DOGS ONLY. CATS ARE NOT ALLOWED.brbrSecurity Camera Notice: The driveway and front of the home has cameras for security and safety measures.brbrA SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.brbrVR Certificate # VR22-00134
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Sleep 10

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$628.31

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Condo

Beachside Elegance • 2 Pools + Gulf View

Siesta Key, Florida, United States

Summary:brbrExperience refined coastal living in this newly refurnished 2BR/2.5BA condo, where luxury meets relaxed island charm. Enjoy elegant décor, 800-thread-count linens, and a gourmet kitchen with granite and stainless steel. Sip coffee on the balcony with a Gulf breeze, unwind by two pools, or stroll to Siesta Key’s white sands. Includes Wi-Fi, fitness room, in-unit laundry, and space for up to six guests. Perfection! 2 week minimum January thru April. 1 week min May thru DecemberbrbrbrbrThe Space:brbrEnjoy a seamless arrival at Crescent, a keyless entry resort. Your access codes will be emailed to you before you arrive.brbrbrbrGuest Access:brbrYour stay includes access to the gated community and its grounds, which can be accessed using a code provided. The apartment is situated on the third floor, with elevator access for convenience. Covered parking is available within the building.brbrbrbrThe Neighborhood:brbrOur condo offers an ideal location directly on the stunning white sands of Siesta Key Beach. Across the street, you'll discover a wonderful selection of shops and restaurants. Enjoy a sweet treat with ice cream, get your caffeine fix with coffee, savor refreshing cocktails, or indulge in delicious donuts. For outdoor adventures, you can conveniently rent bikes, kites, kayaks, paddleboards (SUPs), scooters, and a variety of beach games. Everything you need for an unforgettable family vacation is easily accessible, ensuring a fun and relaxing experience for everyone!brbrbrbrGetting Around:brbrSiesta Key presents effortless accessibility. A curated selection of fine dining establishments, sophisticated bars, and exclusive boutiques are situated within easy reach. For those inclined to explore further, bicycle or scooter rentals offer a delightful alternative. A complimentary public trolley service, operating at thirty-minute intervals, gracefully traverses the island, connecting the northern and southern locales, including the charming village and the serene Turtle Beach. Complimentary parking is also provided for those who prefer the convenience of driving.brbrbrbrOther Things to Note:brbrFor your convenience, a House Manual is provided. This manual contains detailed instructions on using the television, accessing the internet, and other essential passwords. You will also find helpful maps, directories, and information about local restaurants and attractions to enhance your stay and make your visit more enjoyable. The manual may also include details about local transportation options, emergency contact information, and any specific house rules or guidelines to ensure a comfortable and safe experience for you and your family.brbrbrbrInteraction with Guests:brbrWe are readily available throughout your stay to assist with any needs or questions you may have. Our office is located just across the street from Crescent Beach at 6555 Midnight Pass Road on Siesta Key. You can reach us easily through the platform messaging system, where we aim to respond promptly. For urgent matters outside of regular business hours, please feel free to contact us at 941-400-1226.
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Exceptional(1)

$845.58

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Private Vacation Home

112 Columbus Blvd in the Village of Siesta Key

Siesta Key, Florida, United States

Summary:brbr3 bedroom, two and a half-bath home in the heart of SK Village. The living room and 2 bathrooms exude sophistication with their Italian Travertine flooring, while the den and kitchen offer durable and stylish floor tiling. Stay entertained with our 3 TVs, perfect for cozy movie nights. Please note that small dogs are warmly welcomed with a pet fee. ($300) The accommodation is thoughtfully designed to comfortably host your group with one king bed, one queen bed, two twin beds, and one aero bed,brbrbrbrThe Space:brbrYou will receive Check in and Check out instructions prior to your arrival. Please check your email.brbrbrbrGuest Access:brbrPrivate entrance and garage.brbrbrbrThe Neighborhood:brbrWalking distance to the village and to the beach.brbrbrbrGetting Around:brbrOpen air free cabs. Frog Hops, rentable golf carts via Zoom-around with Siesta 4 Rent discount.brbrbrbrOther Things to Note:brbrPlease note that a comprehensive Siesta 4 Rent Home Guide Book detailing home operations and island resources, is readily available for your convenience. We kindly request that you familiarize yourself with this guide upon arrival. If you note any additions you think should be included, please do let us know, and we will be happy to include them for you and our next guests. Thank you for being a guest of Siesta 4 Rent.brbrbrbrInteraction with Guests:brbrWe are available to assist you during your stay. Our office hours are Monday to Friday, 9 AM to 4 PM, and Saturday, 9 AM to 3 PM. For any urgent matters, we're reachable 24/7. The best way to reach us is via the platform's messaging system, where we aim to respond promptly. We're here to ensure your stay at our Siesta Key home is seamless and enjoyable.
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Exceptional(3)

$282.15

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Condo

Peaceful Siesta Key condo - short stroll to the beach - GBB 1219

Siesta Key, Florida, United States

Discover the charm and convenience of this delightful 2-bedroom, 2-bathroom condo, ideally located just a short stroll from the beach. Professionally managed by Gulf Coast Vacation Rentals. This inviting Key West-style condo boasts a very rare 2-car garage, providing ample parking and storage space. Set within a beautifully landscaped property, the condo offers a serene and picturesque setting, surrounded by lush greenery and palm trees.brbrOne of the unique features of this ground-floor unit is that it does not have a unit above it, ensuring a peaceful and quiet living environment. The condo is impeccably clean and comfortable, with every detail thoughtfully attended to. The fully stocked kitchen allows you to prepare and enjoy meals with ease, while the provided linens and beach equipment ensure that your vacation is both easy and carefree.brbrThe community offers a wealth of amenities to enhance your stay. Take a refreshing dip in one of the two swimming pools, or engage in a friendly game on the tennis court or pickleball court. For those looking to stay active, there is a well-equipped workout room available. Additionally, a fishing dock is available for residents who enjoy spending time by the water.brbrCome and experience the perfect blend of relaxation and recreation in this charming condo. Whether you're lounging by the pool, enjoying a game of tennis, or exploring the nearby beach, this property offers everything you need for a memorable vacation.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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Home Most popular vacation rentals in Siesta Key