Vacation Home Rentals By Owner In Siesta Key, FL

$3110.58

Beachfront Luxury - Resort Pool - Steps to Village

Siesta Key, Florida, United States

Summary:brbrVunique Vacations was built for the discerning traveler who’s seeking a truly unforgettable experience! Each home is thoughtfully designed down to the last detail, with you–our guest–in mind. Our team delivers service that’s every bit as impressive as our luxury vacation homes, with a consistent, personalized touch from start to finish. No hidden fees, just transparent pricing and advertising. The result Unmatched value for travelers who expect more from their getaway.brbrbrbrThe Space:brbrSunset Blue is the best beachfront property on Siesta Key, and one of the best in Florida! It is set up for the ultimate vacation! Your family vacation photos have never looked better! It provides a private beach with amenities, outdoor covered patios, balconies, a pool area, and entertainment space. The tear drop shaped, heated saltwater pool and spa are not mirage, this is your beachfront oasis! With a tapered sun shelf with bubblers, large turf area with loungers, and a basketball hoop and cornhole boards for those active travel members this is a pool area for everyone! The covered patio space features a pool bar, outdoor dining, and soft seating as well. These spaces are all within the fenced backyard for privacy and security, making it family friendly. You’ll be able to enjoy sunset skies from anywhere within this space! As you go up in this home, you’ll find amazing views from almost every space and all the home’s balconies on all levels. Get used to wide open Gulf of Mexico and Siesta Key Beach views.brbrbrbrOnce inside this approximately 4,200 square foot home, you will immediately notice the elevator with service to all floors, as well as the high ceilings, huge windows and sliding doors to maximize the amazing views from nearly every room, and the incredible craftsmanship and design throughout. This luxury rental home on Siesta Key provides 5 bedrooms (all with en suite baths) and 5 full baths and 2 half baths throughout the home. There are 4 king beds, and a custom-built queen over queen bunk bed. It comfortably sleeps 12 people in beds. The great room is set up as the perfect gathering space as it includes the kitchen, living, and dining areas of the home with access to multiple balconies. The kitchen is fully stocked, and we mean that because we know how important it is to you, our valued guests! Not only is it stocked, but it’s also stocked with the products and manufacturers you trust. Additionally, this home features a club room or secondary living space. The club room features a wet bar area, living room and TV, multiple game options, and access to another oversized balcony.brbrbrbrFloor Plan Description (by level):brbrbrbrGround Level:brbrFree parking for up to 5 vehicles (3 covered spaces, and 2 spaces in the driveway). On this ground level you’ll find the fully fenced pool and backyard area that includes the pool and covered patio spaces! The covered patio features an outdoor grill (natural gas), a pool bar with beverage fridge and bar seating for 3, as well as outdoor dining for 8, and various seating options and ceiling fans throughout for added comfort. Just off this pool area is your private beach access with seating and a beach volleyball court. The home’s beach equipment can be found here, which includes 2 beach wagons, 2 coolers, 12 beach chairs, and 4 bikes. We include a full refrigerator nearby for easy storage of food, drinks, and ice, so your beach prep and breakdown are that much easier. These appliances can also be used to support your pool days and time at home as well. You’ll also access the home’s main entrance foyer with elevator and stair access to the home's two (2) living levels above.brbrbrbrThe First Level of Living (2nd Floor):brbrThis level features a great room with the fully stocked kitchen and includes a range with cooktop with hood vent, double ovens, full sized refrigerator (with ice maker) and freezer, double trash and recycling storage, microwave, toaster, coffee maker, and is very well appointed with cookware, bakeware, dishware, cutlery, and specialty items like crockpots, blenders, and more. If you have any questions on kitchen supplies, our reservationists would be happy to provide more details. The living area is very comfortable and offers Gulf views. The dining area here seats 15 people comfortably via an 8-person dining table and 7 additional seats at the kitchen island bar top. The main balcony on this level is directly off this great room and it connects to it perfectly. It offers additional outdoor dining for 6, soft seating, ceiling fans for comfort, and stunning views of the Gulf and beach. There are 2 bedrooms, including the master bedroom, and a study on this floor. The master features stunning Gulf views, a king bed, walk-in closet, and an oversized en-suite bathroom with double vanities, a large separate shower, and free-standing soaking tub. Bedroom 2 features a king bed, en suite bathroom with a vanity and walk-in shower, and balcony access with peaking Gulf views. Also located on this floor is a shared half bath and laundry room.brbrbrbrThe Second Level of Living (3rd Floor):brbrFeatures a club room offers direct Gulf views that are truly jaw dropping. It has a wet bar, dining space for 6, a living area, large TV and Nintendo Switch gaming console, half bath, and an oversized balcony. The balcony offers an elevated outdoor living space, with dining and seating options, ceiling fans, and unbeatable views! There are also 3 Bedrooms on this floor. Bedrooms 3 and 4 both feature a king Bed, and an en suite bath with a walk-in shower and vanity. Bedroom 5 is the home’s bunk room featuring custom-built queen over queen bunk beds with built in storage and shelving and an en suite bath with a vanity and a shower/tub combo. Also located on this floor is a shared ½ bath and laundry room.brbrbrbrGetting Around:brbrPrivate Beachfront Home! Enjoy private beach access to the world-famous Siesta Key Beach, with your very own private volleyball court and seating area. You’re also steps to the entrance to Siesta Key Village and its restaurants, entertainment, shopping, grocers, and more. It has a 100% walkability score to everything you need! If you want to explore further, without the hassle of driving, you’ll find multiple stops nearby for the free trolley that provides transportation service to the entirety of Siesta Key. You’re also just a quick drive or Uber/Lyft (10-15 minutes) to downtown Sarasota for access to the amazing Sarasota Performing Arts scene, and numerous fantastic restaurants, shops, marinas, bars and entertainment, and more. And, day trips to Lido Key and Anna Maria Island are just 30 minutes away, as well as the amazing theme parks of Tampa and Orlando that are all just 1-2 hours away!brbrbrbrOther Things to Note:brbrThis Siesta Key luxury vacation rental features Smart TVs with cable and streaming services, as well as Free Wi-Fi throughout the property - including the outside areas for complete coverage for all your work or personal needs. TVs in all bedrooms.brbrbrbrAccessibility - in addition to the home’s elevator access to all levels, most doorways and walkways are 30 inches or larger and walk-in showers featured in most bathrooms. Please see the Photos, 3D Tour, & Video for this home for exact information.brbrbrbr*Don't forget to check out our Matterport 3D Tour for this home* And, if you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team of professional reservationists and we will be happy to assist you. We want you to fully understand what you are booking, and yes, an actual human team member is available to help! You are just a couple of clicks away from paradise!brbrbrbrInteraction with Guests:brbrPersonal service and attention to detail define the Vunique Difference. We want your vacation to fit your schedule, which is why we offer flexible bookings starting at just 3 nights for most of the year and any-day arrivals. Our homes are spacious and thoughtfully designed, made for connection as much as comfort. Here, luxury isn’t an upgrade – it’s the standard. Within our portfolio of branded residences, you have every amenity that you need for an unforgettable stay - waterslides, movie rooms, resort-style pools, sport courts, golf simulators, climbing walls, putt-putt courses, zip lines, gaming systems, rooftop decks, biked and beach equipment and more. Our proactive maintenance team ensures everything is in top shape before your arrival, and each property has a dedicated manager who welcomes you personally and stays available throughout your stay should you need anything. Transparency is at the core of everything we do. What you see is what you pay – no hidden fees for pool heat (up to 86 degrees), bikes, propane, or any of the extras that should already be included. Why settle, when you can stay somewhere extraordinary

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$370.42

/ Nightly

Private Vacation Home

The Coastal Nest - Upscale Residential Home!

Siesta Key, Florida, United States

The Coastal Nest by Tropical Sands AccommodationsbrbrWelcome to The Coastal Nest, an upscale three-bedroom, two-bath vacation home tucked away in a quiet residential neighborhood of Sarasota. Designed for comfort and longer stays, this inviting retreat offers a relaxed coastal atmosphere, thoughtful amenities, and a convenient island location ideal for guests seeking a peaceful home base near Sarasota’s renowned beaches, dining, and outdoor activities.brbrWith flexible stay requirements throughout the year and a layout well suited for couples, families, or seasonal visitors, The Coastal Nest delivers an easygoing Florida lifestyle with all the essentials for a comfortable getaway.brbrHighlightsbr• 3 Bedrooms / 2 Bathroomsbr• King bed, 2 Queen bedsbr• Washer and dryerbr• Beach chairs and beach cartbr• Upscale residential homebr• Quiet island neighborhoodbr• Flexible stay requirementsbr• 2 Parking spotsbr• Convenient Sarasota locationbrbrThe Coastal Nest is equipped with practical comforts that enhance everyday living. Beach chairs and a beach cart make trips to the shoreline simple and enjoyable, while the washer and dryer add convenience for longer stays. This home’s thoughtful setup makes it especially appealing for guests planning extended visits to the Sarasota area.brbrInside, the home features a comfortable and welcoming living area designed for relaxing after a day of exploring the coast. The kitchen is well equipped for daily meal preparation and casual dining, offering a functional layout that supports both short and long-term stays. Nearby dining space provides an inviting spot for shared meals, morning coffee, or planning the day ahead.brbrThe primary bedroom offers a restful retreat with a king bed and a private ensuite bathroom featuring a walk-in shower. Two additional guest bedrooms are furnished with queen beds and share a hallway bathroom with a shower and tub combination, providing comfort and convenience for guests or family members.brbrRoom Detailsbr• Primary Bedroom: King bed with ensuite bathroom and walk-in showerbr• Second Bedroom: Queen bedbr• Third Bedroom: Queen bedbr• Hall Bathroom: Full bathroom with shower and tub combinationbrbrAdditional features include beach gear for guest use and in home laundry facilities. Please note that the garage and golf cart are reserved for owner use only.brbrSettle into relaxed island living at The Coastal Nest by Tropical Sands Accommodations. With a comfortable layout, essential amenities, and a prime Sarasota location ideal for seasonal or extended stays, this home is a wonderful place to unwind and enjoy Florida at your own pace. Book your stay today and make The Coastal Nest your next coastal retreat.brbr-brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis home requires a minimum 30-night stay in accordance with local city regulations, and shorter stays are not permitted.brbrThis property does not allow pets of any kind.brbr2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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$512.54

/ Nightly

Private Vacation Home

Lovely Siesta Key house near beach w/ heated pool

Siesta Key, Florida, United States

Welcome to Che Bella Casa - A charming wonderful home located walking distance (1 block - ca 300 yards/3 minutes walk) from US ranked #1 Siesta Key beach. Restaurants and dining facilities are ca 800 yards. Featuring 2 en-suite bedrooms and an additional bedroom with an open plan kitchen. Step outside to discover the private backyard, with pavers surrounding the sparkling private pool. This family friendly home welcomes kids as well as small pets.brbrOther things to note:brbr1. Pool Heating (7am - 7pm) for 84F can be booked at $25 per day.brbr2. Please be advised that we don't provide consumables e.g. toilet paper, kitchen rolls, garbage bags, dishwasher and washing machine tabs. Therefore guests are required to buy these for their use for the rental period.brbr3. During peak season (January - April), check-in/out is on Saturdays only.

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$314.01

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Private Vacation Home

Spacious Siesta Key Home with Private Heated Pool – Pet Friendly, Near Beaches

Siesta Key, Florida, United States

Beautiful 2 story home with a 2 car garage and pool located in the desirable neighborhood of Bay Isles on the island of Siesta Key. The home has an open floorplan with vaulted ceilings and lots of windows for a spacious, bright and airy feeling. The living room is quite large with a very comfortable sectional sofa, digital flat screen TV and DVD player. Free cable and WiFi are provided. Sliding doors with wooden shutters give access to the outdoor patio and pool area from both the living room and bonus room. Home has a full size washer and dryer just off the kitchen tucked away in a large laundry closet with doors so it is hidden when not in use.brbrThe home sleeps 9 comfortably with 3 bedrooms plus an additional bonus room with pull-down Murphy bed.The master bedroom and bathroom are located upstairs and there are 2 walk-in closets, king size bed, and flat screen TV. The master bath has an oversized jetted spa tub, bidet, shower and separate private toilet area. There are 2 bedrooms, the bonus room, and one bathroom downstairs. One bedroom has a queen bed and a large closet with built in shelves and drawers. The other bedroom has a bunk beds with a twin on top and full (standard) on the bottom, as well as a trundle that makes into a full size bed. The bonus room features a comfortable couch and a pull-down Murphy bed.brbrThe pool is heated (solar), screened in, private and sparkling clean. There are 2 patio areas (upper and lower level). BBQ grill, patio furniture and lounge chairs are also provided.brbrA lot of extras are supplied to help make your vacation here a memorable one, including beach toys, beach chairs, coolers, pool toys & floats, tennis racquets, football & soccer balls, to name a few.brbrThe public beach (lifeguard stands, concession stand, restrooms) is about a 5 minute drive from the home. Take a short 5 minute drive to Siesta Key Village to enjoy great restaurants and clubs with live music, ice cream shop, convenience store, and plentiful shopping.brbrSmall dogs will be considered with a $200 non-refundable pet fee but we must be notified before your reservation can be confirmed. The pet fee is in addition to the online price quote and will be charged before final processing & confirmation.brbrCity of Sarasota Certification of Registration: VR23-00016

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$357.49

/ Nightly

Private Vacation Home

Doveplum 810 - 2 Story, 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided...

Siesta Key, Florida, United States

ONLY A BRIEF 5 MINUTE WALK TO OUR PRIVATE PIECE OF CRESCENT BEACH!Gorgeous, updated 3 BD/2.5 BA two story townhouse overlooking the tranquil canal and tropical greenery. Located on the ground floor is the spacious living room with 50 flat panel TV,DVD,VCR, CD stereo and high speed internet access. Open slider doors and step out to tropical grounds and boat docks. First floor also features large kitchen, dining room and half bath. Walk upstairs to the three bedrooms and two bathrooms. Master bedroom features a king bed and TV. Master bathroom has tub/shower combination. Open sliders to view of the canal. Second bedroom has queen bed and TV. Third guest bedroom has two twin beds and TV. Guest bathroom has shower only. Washer/dryer on second level. Complimentary Wi-Fi in unit. 2 Heated Pools, 2 Lighted, Private Tennis Courts, BRAND NEW Fitness Center, Newly Remodeled Clubhouse with Computer, Printer and Wi-Fi, Beach Attendant with complimentary use and set-up of beach loungers and umbrellas 7 days a week! Unit sleeps a maximum of no more than 6 people. Enjoy your vacation in one of the premier units at Midnight Cove!

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$807.37

/ Nightly

Private Vacation Home

Holiday House | Steps to Siesta Beach, Pet Friendly, Walk to Village

Siesta Key, Florida, United States

Holiday House - Steps to Siesta Beach, Pet Friendly, Walk to Siesta Key Villagebrbr Why You'll Love This HomebrHoliday House gives you that rare Siesta Key experience where the beach, the Village, and your own bright upstairs retreat all feel effortlessly connected. Spend your days wandering from soft white sand to cool indoor comfort, then back out to lively evenings just steps away. The home feels cheerful and easy, with space to gather, room to relax, and a breezy island atmosphere that makes every moment feel like vacation.brbr ‍ ‍ Perfect ForbrFamilies and small groups who want walkability, pet-friendly comfort, and a laid-back island atmosphere.brbr ️ Imagine ThisbrYou start your day with complimentary beach gear in hand and head to the beach, just steps away from your home. The breeze carries faint salt air, reminding you that Siesta's famous white sand is just moments away. Beach chairs and towels in hand, feeling that light vacation excitement as you walk toward the Gulf.brbrAs the sun dips low, you fire up the grill beneath the Tiki cabana and watch the sky glow with soft streaks of orange and coral. Every part of the day feels smooth and unhurried—like the island itself is reminding you to breathe, slow down, and savor the moment.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath with Walk-In Shower, TVbr• Bedroom 2: King Bed, Hall Bath, TVbr• Bedroom 3: Two Full Beds, Hall Bath, TVbr• Living Room: Queen Sleeper Sofa, TVbrbr Explore the Areabr• 300 Feet to Siesta Key's Sunset Beachbr• 0.1 Miles (2-Minute Walk) to Siesta Key Villagebr• 0.1 Miles to Local Dining, Coffee Shops and Boutiquesbr• Free Siesta Key Breeze Trolleybrbr⌛ Don't wait—This home is in the perfect location! Your reservation includes peace of mind with our CottageClean™ program, featuring a detailed 6-hour deep clean and a 35-point inspection before every arrival.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Your furry friend is welcome! This property is dog-friendly for dogs under 25 lbs with an additional pet fee. Breed restrictions apply. Please notify us in advance if you'll be bringing a pet. The home is part of a duplex and located on the second floor. It may share walls, floor/ceiling, or outdoor spaces. If any guest has difficulty with stairs, please contact us for alternative accommodations.

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$932.2

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Private Vacation Home

Luxury 4-bedroom Penthouse in Siesta Key- Private rooftop terrace

Siesta Key, Florida, United States

Experience one of the most exceptional penthouse residences in all of Siesta Key. Perfectly located in the heart of Siesta Key Village, this luxury condo is truly unmatched in location, size, privacy, and amenities.brbrEnjoy the exclusivity of a private elevator entrance, private garage, private rooftop terrace, and six exterior balconies, offering multiple spaces to relax, entertain, and soak in the coastal atmosphere.brbrThe main living area features a spacious open-concept design with ample seating, ideal for gathering with family and friends. The chef’s kitchen is fully equipped with top-of-the-line, state-of-the-art appliances and everything needed to prepare meals for the entire group. Adjacent to the living room, the dining area seats eight comfortably, complemented by additional bar seating at the kitchen island.brbrA second living space serves as a dedicated game and entertainment room, complete with a bar-style kitchenette, full-size refrigerator, microwave, ping-pong table, TV lounge, and a chess coffee table. This area opens to its own private balcony, making it an ideal retreat for teens or guests looking for a separate space to unwind.brbrSleeping accommodations are perfect for large families or groups, comfortably sleeping up to 10 guests:brbrTwo luxurious king master suites, each with a private ensuite bathroombrbrOne guest bedroom with a queen bedbrbrOne guest bedroom with a bunk bed featuring a queen on the bottom and a Double XL on topbrbrGuests also have access to a heated outdoor pool and spa, along with a private grill for enjoying BBQ meals with family and friends.brbrFor your beach days, Coastal Oasis includes complimentary beach equipment—chairs, umbrella, and beach buggy—for your convenience.brbrAdditional details:brbrSleeps up to 10 guestsbrbrNo pets allowedbrbrMinimum age requirement: 25 years old

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$398.35

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Private Vacation Home

Charming, newly renovated townhouse on beautiful Siesta Key beach.

Siesta Key, Florida, United States

Welcome to Siesta Beach House, where a private beach and heated pool await you. Kickback, relax, and immerse yourself in the tranquil surroundings as you enjoy your well-deserved vacation. Unwind by the pool, stroll along the pristine beach, and let the soothing sounds of the gulf wash away your worries. Your perfect getaway starts here at Siesta Beach House Stay comfortably in Siesta Key at this 2-bedroom townhome. The bedrooms feature 1 king bed, 1 queen bed, and 1 double bed, ensuring a delightful night's sleep for all guests. With amenities like WiFi, AC, and a hair dryer, your stay will be enjoyable and stress-free. The property also offers 2 bathrooms with a shower and other essentials. Escape to this tranquil retreat and create lasting memories with your loved ones. We'll be available to answer any questions while you stay at our place.

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$337.9

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Private Vacation Home

Renovated Townhouse With Private Beach Access!

Siesta Key, Florida, United States

Gulf & Bay Club Bayside is a Resort complex of Key West style Town Homes all with one car attached garages. Gulf & Bay Club Bayside offers :brbr*two heated pools br*clubhouse with exercise/workout center and sauna br*two lighted tennis courts br*fishing pier br*walking paths br*picnic areas with Weber gas grills br* private deeded beach accessbrbrSiesta Key has been voted top beach in the nation. Recognized for its white sands beaches and low key, relaxing beach vibes. We recently have had extensive renovations throughout our condo. We are excited to share it with you. Our condo is 1100 sq ft of indoor / outdoor living with private beach access. The master bedroom includes king-sized bed, a walk-in closet and double marbled topped vanity with walk in shower. Guest bedroom includes queen bed with closet. Updated guest bathroom, equipped with shower and tub with marble topped vanity. Kitchen updated with new cabinetry and granite counter tops, updated appliances and is fully equipped with kitchenware. Sleeps six people maximum, note the extra charge for more than four people on rate-notes page. Both bedrooms have new SMART TV’s (Access to Netflix, Youtube, etc.). All linens included and beach towels. Laundry area located within the condo with washer and dryer. Screened Lanai is accessible from the Living room. The house is maintained and updated to the utmost - towels, sheets, furniture, flooring, etc. Living room has a sleeper in front of an entertainment center with a 65” LED Flat SMART TV. A total of 3 HD SMART tvs with full cable and. FREE HIGH-SPEED WIRELESS INTERNET AND PHONE.brbrOnly about 1.5 mi from the village filled with restaurants, bars, shops and groceries. A short walk to private beach access as well as a short walk to the public beach which contains, BBQs, covered picnic table, showers and playground. Directly located across community pool. Inter-coastal fishing access directly located in walking distance to condo. It's the perfect unit, with the perfect location, in the perfect beach. Top rated Gulf coast beach.

2

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2

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6

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$255.87

/ Nightly

Private Vacation Home

Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

Siesta Key, Florida, United States

“Pristine sand, blue skies - 'Number 1 Beach'” brbrThe Best Thing to Come Home to after a Day on the Beach Is...br ...a vacation home as comfortable as your own. brbr1103 Lake House Circle, Siesta Key Fl 34242 unit 107brbrJust a walk across the street to Siesta Key's world famous #1 Beach.brbr This split-level townhouse, has 2 bedrooms, 2 baths and feels like home. Features include a one car attached garage, an open great room concept with elevated dining area, and 20 ft of balcony space overlooking a lake. This townhouse is conveniently located across from Siesta Key's Public Beach and the complex has both tennis courts and a heated pool with covered pavilion and BBQ area.brbrbrSleeps 6 -- king in master, queen in second bedroom and queen pull-out sofa bed. We also have a washable/portable crib and portable single cotbrbrFull-Sized Washer/dryer in unitbrbrFull eat-in kitchen includes: brDishwasherbrbrMicrowavebrSlow CookerbrCoffee maker (new K-Cup)brRegular full-sized electric coffee potbrBlenderbrToaster brbrToaster Oven brbrPassword protected High Speed InternetbrbrTelephone with free International callingbrbrWi-Fi accessbrbrFull Cable televisions in both bedrooms and Living Room brbrDVD players in both bedrooms and living room brAssorted DVDs to watch (including children's titles)brFull linens and towels including beach, pool and bath towelsbrbrHair dryersbrbrFor Beach:brAssorted beach chairs, beach toys and floats, boogey boards and skim boardsbrbrAn adult Beach bicycle with front basketbr2 children's bicyclesbrbrRates are all-inclusive- just add Fl room tax-- no extra hidden charges-

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$371.77

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Private Vacation Home

Siesta Beach Vacation Rental

Siesta Key, Florida, United States

This 1940's Vacation Home, less than 200 feet from Siesta Beach, was recently upgraded in 2015 with all the modern conveniences, including a beautiful private pool with sun-shelf and barbeque for your entertainment and relaxing pleasure. There is a formal dining area and plenty of relaxing space, including a in-door bar area over looking the pool. This house has multiple driveways and is capable of handling a small RV and/or motorcycle trailer, etc. ... Paddleboard rental is optional and some beach supplies are included. Cable and WIFI included. Blender, coffee maker, hair dryer, etc. are also basic features.

2

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1

Bath

4

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$1656.58

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Private Vacation Home

5 STAR SIESTA KEY, 80 STEPS to BEACH, LUXURY POOL, 6 BEDROOMS, SPACIOUS LIVING

Siesta Key, Florida, United States

For those seeking a truly amazing vacation experience! Come and experience the very BEST in hospitality on Siesta Key. Our property is a beautiful spacious retreat in the best location. brbrOur average length of stay requirements vary between 4-14 nights, and 7 nights during our high season. If the travel dates you are looking for do not meet our advertised minimum requirements, please contact me directly and I will see if we can accommodate your request.brbrStunning and spacious 555 Beach Road. The home offers more than 3600 square feet of sophistication inside and a large private back yard oasis with resort pool area. Equally important - a truly amazing location 90 feet to beach access 10. Unlike other vacation rentals, you Avoid long walks and crowds - we are directly across from a more private section of the number beach in the entire US. Our guests walk back and forth throughout the day to Siesta Key Beach, the # 1 Beach in the US - and walk to Siesta Village and its great restaurants for meals. brbrWe work hard to make this the perfect vacation home and check to make sure you are taken care of while you are here. Our Brand new fully stocked chef's kitchen with quartz countertops & white lacquer cabinetry makes for great entertain. The house comes with beach caddies, beach towels, beach umbrellas, beach toys, and more. brbrPlease note that our vacation home consists of two units under one roof offering more privacy - with the ease to move back and forth. This listing is for both units, 6 bedrooms, 4.5 baths, plus two outdoor heated showers. The two units together create one of the most spacious 6-bedroom 5-baths on Siesta Key! Our home sleeps 14 very comfortably. If you need more flexibility with sleeping arrangements we have high-end air mattresses in each unit. brbrThe two units under one roof work well together as the front doors to each unit face each other, so it's convenient to move back and forth. Inside the spacious front unit, enjoy wonderful light as you walk into an expansive living room and great open kitchen (with bar and a separate dining area), making this a perfect spot for entertaining. Continue the party - or simply relax and take in the sun - wall to wall sliding glass opens onto the outdoor balcony with dining area, relaxing sofa, and partial water views. Upstairs are 3 bedrooms, 2.5 baths, with balcony and partial water views. The Master bedroom has a King bed set, outdoor balcony, large walk-in closet, and ensuite bath with 2 sinks, jacuzzi tub, separate shower, and toilet. The 2nd bedroom has two queen beds, shared balcony, large walk-in closet and the third bedroom has two twin beds. The 2nd large bathroom upstairs has separate shower and separate tub. The main living level offers a 3rd - 1/2 bath, a separate washer/dryer room off the kitchen. The property also two showers outside. brbrThe beautifully furnished 3 bedroom 2 bath pool facing unit is spacious with a dining, kitchen and living area. The living room has large sliding glass doors opening up to a balcony and dining area that overlooks the backyard, palm trees, and our stunning resort pool. The bedrooms are upstairs. Two bedrooms have king beds and the third bedroom has a queen. We provide high end linens, beach towels, beach caddies, umbrellas, beach toys, and more. brbrNEW RESORT POOL AREA & PRIVATE BACKYARD to play in. The lush and tropical landscaped backyard offers 3 dining areas, BBQ grill, and a new gorgeous 25-foot heated pool. Home fully equipped with new furnishings and all the upscale amenities, fully loaded for discerning travelers. Additional New features throughout: new Air Conditioning and new a/c duct work (great for anyone with allergies.)brbrWe live on Siesta Key to make sure your stay is wonderful. It's worth noting: beach access is right across the street from our home - this a big plus. Some homes, even though they are on Beach Road are not close to beach access. brbrOur address is 555 Beach Road, right across from the beach and 1/2 mile walk to Siesta Village restaurants. brIf you only need 3 bedrooms, each unit can also be rented separately (see property 977754.) The backyard deck (exclusive to the pool-facing unit) has an outdoor dining table overlooking the pool and backyard. The front-facing unit has a balcony with a dining table, lounge furniture, and partial views of the beach. brbrThe property is located directly across the street from Siesta Key Beach, ranked the number one beach in the entire US.brbrAdditional notes: Two bedrooms in the front unit offer large walk-in closets. Bathrooms are large and spacious. Please see pictures for more details. We offer high speed internet and have new high definition flat screens throughout. Please note: our published rates are subject to change. While we offer fewer than 7 day rentals during the Fall and some off season weeks, we require minimum 7 day stays during most holidays and during our busy seasons. Please email if you have any questions. brbrTo understand more about our commitment to you and hospitality, please read our reviews.

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$904.0

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Private Vacation Home

Mid Century Lux- pool / canal house walk to the village

Siesta Key, Florida, United States

Ideally located on Siesta Key, walk to the beach and village from this canal front, pool home. 4 unique and cozy bedrooms (3 kings, 1 queen), 3.5 baths. Thoughtfully designed and furnished to maximize comfort and style. Very spacious indoor and outdoor living space. Gorgeous tropical yard with whimsical features, solar heated pool, canal, and privacy! We also have a 2 person kayak, and 4 beach cruisers. Easy bike ride or walk to the village and beach.

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$366.03

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Private Vacation Home

Private back yard with heated pool. Pet friendly 3 bedroom house, close to beach

Siesta Key, Florida, United States

Come and enjoy this pet friendly private house with your very own secluded heated swimming pool, in beautiful Siesta Key. Discounts are offered for stay of 4 weeks, winter months excluded. We love to have our house rented so throw us your best offer and we will consider it. Our Siesta Key Tropical Pool Paradise home is a 5 Min walk to the #1 Rated Beach with the best white sands you have ever seen. 10 Min walk to the village where you will find great local restaurants, your choice of ice cream shops, live music, village grocery store and liquor store - you won't need to head to the main land. Our renovated house offers you a home away from home with a full kitchen at your disposal if you choose to eat in. Our in ground heated pool is surrounded by a lush tropical oasis. We have completely renovated our house and are so happy to share our new and improved vacation home with you. This is the place you'll want visit, and return year after year. Check in times is 4 PM and check out time is 10 AM.br*** Please Check out our other listing #1085215, also on Siesta Key, just two streets away *** Please ask any question you might have about our house or our neighbourhood. We are here to help you make a good vacation choice for your vacation needs.

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$298.23

/ Nightly

Private Vacation Home

Big Siesta Key Rental Home With Caged Heated Inground Saltwater Pool And Hot Tub

Siesta Key, Florida, United States

This home provides an awesome private solar heated in-ground pebble-tec pool and hot tub in a huge paver deck and caged lanai. 4442 sqft of living space including Lanai gives you lots of elbow room to relax. A paver pathway around the house to view the lush tropical gardens that adorn this property. It is fully furnished with many amenities and necessities, just bring your smile... you will be using it.brbrThe Tree House is our beautiful Key West style 2 story, 3200 sq-ft, 4 bedroom, 3.5 bath house available for rent for up to eight people in the heart of Siesta Key on a secluded circle drive. Situated on an exclusive barrier island close to Sarasota, this home is on an official canopy road at Twin Oak Pond just a minutes drive or easy walk to the #1 best beach in the USA, Siesta Key Beach. There is a two car garage with lots of additional parking on the paver driveway... you have arrived at THE TREE HOUSE.brbrThere are full kitchens with stoves and microwaves, and dishwashers on both floors all with under-cabinet lighting. A pool bar with bar fridge assures libation is close at hand. Very updated with hardwood floors and tile, along with high end granite and Silestone. Washer and Dryer on both floors. Three central heating and air conditioning systems. Large flat-screen television the way you like it. High speed internet on WIFI ready to go for you. Stereo tuner / CD player and eight channel speaker system throughout the house makes for easy listening of your favorite music wherever you are. Filtered water throughout the house. 24/7 fully monitored security system for every opening in the house, plus monitored smoke detection, plus five motion detectors ensures you and your possessions are safe and secure.brbrThe house has 4 showers so try a new one each day. Nice bathrooms are a must in my book. There are 8 sinks in the house, 3 with disposals built in. 8 spigots with garden hoses... you can even wash your car inside the garage... the floor is pavered and the hose is right there for you! The Sunbrella canopy on the second floor deck can be opened or closed easily... want more sun Go for it! Want less Close the canopy! The pool is a solar heated saltwater pool! If you have never used one you are in for a treat and your skin will thank you... no jugs of chlorine sitting around and burning your eyes when you swim in it... now you are in a saltwater pool at 2800 parts per million. PERFECT! There are benches inside the pool all around so you can rest from a hard day of frolicking... but never have to leave the pool! SWEET! The in-ground hot tub is the perfect place for your entire party to sit and realize... you have made it! This place is VERY, VERY private. I love that! No more tromping around the hotel pool with strangers about. It is all you! Quiet and comfy and private. Do you like the soothing sound of waterfalls Don't worry, The Tree House has three of them at the flip of a switch! How cool is that There are 3 big bedrooms, 1 small bedroom. Master king sized bed, two queen sized beds, one queen sleeper, one twin bed, one twin sleeper. It has it all and it's waiting for YOU! You only live once, so make it count!brbrAccommodation is plus tax and cleaning fee. A damage deposit is required. brbrThis is a spectacular private home for a vacation. The pics tell the story.brCall, text or email for rental details of this very clean and very well appointed vacation paradise.brAdditional propane pool heat can be purchased by renter if desired.brPlease note* If you are looking for a place to play loud music, or have noisy parties or lots of guests, this is not the place for you. This house is in a quiet setting, with neighbors who must be respected. This rental property is intended for responsible adults and/or families. Thank you.

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$1838.17

/ Nightly

Private Vacation Home

High Tide - Beautiful pool with waterslide, 2 min walk to the beach

Siesta Key, Florida, United States

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Bath

Sleeps

$1074.69

/ Nightly

Private Vacation Home

Oasis with Heated Pool

Siesta Key, Florida, United States

Make some memories at this unique and family-friendly place. Enjoy this lush and tropical pool area that will almost make you forget that a highly rated sometimes rated #1 Beach is just steps away! Provided for you are all the necessary beach items like beach towels and chairs and more! This is a very spacious house and cottage that make up the total of 4 bedrooms and 4 baths. The house and cottage are on the same property.

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$586.73

/ Nightly

Private Vacation Home

Modern Coastal Retreat: 3BR, Private Pool, Walk to Beach, Luxe Outdoor Dining + NordicTrack Gym

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrDiscover your coastal home-away-from-home at The Nest on Siesta Key — a fully renovated, modern-luxury retreat located on peaceful street. Whether you're a snowbird looking to settle in for a sunny winter or a family in search of a high-end summer vacation, this 3-bedroom haven blends elegance, function, and coastal comfort with style. brbr brbrBedrooms & Layout brbr- King Master Suite – Bright and spacious with a large walk-in closet, dual-sink bathroom, and walk-in shower. A bonus flex room connects directly to the suite, offering a plush sofa and a NordicTrack bike — perfect for morning workouts with a pool view. brbr- Guest King Bedroom – Thoughtfully styled and includes a smart TV, closet, and bright natural light. brbr- Kid-Friendly Bunk Room – Features a twin/queen bunk, a separate twin bed, smart TV, and space for 3–4 kids to sleep comfortably. brbr brbrOpen Living Space – Gather in the beautiful living room with a stone-accented fireplace, smart TV, and flexible couch sleeping option. brbr brbrKitchen & Dining brbr- Fully Stocked Gourmet Kitchen – All new appliances, stove, large fridge, dishwasher, microwave, and ample cookware. brbr- Bar Seating + Dining – Barstools for 4 at the kitchen island + a formal dining table for 6. brbr- Bonus Nook – A second dining table (seats 4) ideal for breakfast, reading, or remote work. brbr brbrOutdoor Living brbr- Private Heated Pool – Surrounded by tropical landscaping, the perfect place to cool off and relax For added peace of mind, we’ve installed a pool door alarm as an extra layer of safety. (Note: Pool Heat is extra) brbr- Covered Lanai – Dine with seating for 8, an outdoor smart TV, and shade for sunny afternoons. brbr- Lawn Space – Ideal for little ones or pups to play. (Certain dog breeds okay, but note: one side of the yard is not fully fenced.) brbr brbrLocation Perks brbr- Quiet & Private – Located on the northern side of Siesta Key in a peaceful, upscale neighborhood. brbr- Walk or Bike to the Beach – Just minutes to Siesta Key Beach, consistently ranked the #1 beach in the U.S. brbr- Smart Features & Comforts – Smart locks, beach gear, high-speed WiFi, smart TVs, washer/dryer, driveway + garage parking. brbr brbr brbrQuick Highlights brbr- 2 King Bedrooms + Kid-Friendly Bunk Room brbr- NordicTrack bike & private workout/flex space brbr- Fully stocked kitchen + 2 dining areas brbr- Smart TVs, smart locks, high-speed WiFi brbr- Private pool & luxury outdoor dining brbr- Walk to Siesta Key Beach brbr- Certain breeds of dogs okay (yard partially fenced) - inquire for more information. brbr brbrOther information: brbr- No smoking property brbr- Pool heat extra - reach out for details. brbr- No parties or large gatherings - This home is in a quiet residential neighborhood. We kindly ask that all guests treat the home and surrounding community with the same care and respect as they would their own. brbr brbrWhether you’re here for a month of sunshine or a week of seaside memories, The Nest is your private sanctuary on Siesta Key. Book your luxury island escape today!brbrAll pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs.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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$549.87

/ Nightly

Private Vacation Home

Coastal Getaway | Pool, Hot Tub | Near SK Beach & Village | Resort-Style Outdoor Living + Dock

Siesta Key, Florida, United States

Welcome to The Dockside Getaway on Siesta Key! brbr brbrA sun-filled, high-end retreat that combines indoor elegance with outdoor bliss. This upscale, canal-access property is perfect for families, seasonal visitors, or couples looking to experience Sarasota’s most iconic island in laid-back luxury. brbr brbrLOCATION HIGHLIGHTS: brbr- Minutes to Siesta Key Village for restaurants, shops, and bars brbr- Short distance to Siesta Key Beach with powder-soft white sand and turquoise water brbr- Quiet residential neighborhood for peaceful escapes brbr- Easy access to canal for boating, paddleboarding, or kayaking brbr brbrPROPERTY FEATURES: brbr- 2 bedroom/ 2-bath canal-access retreat (1300 sq ft) brbr- Private, heated pool with sun shelf and lounge seating, partially fenced yard (note: Pool Heat is extra) brbr- Pet friendly: 1 small dog allowed with prior approval and fee brbr- Covered outdoor lounge with dining, seating, and smart TV brbr- Front patio shaded for coffee or cocktails brbr- Private dock across the street brbr- Washer and dryer brbr- Ring doorbell for added security brbr brbr brbrLIVING ROOM: brbr- Indoor elegant space with high-end furnishings, couch doubles as a sofa bed brbr- Open layout connecting to outdoor lounge brbr- Smart TV and streaming capabilities (just need your log in), dedicated wifi brbr brbrKITCHEN AND DINING: brbr- Fully equipped kitchen with modern appliances brbr- Dining table seats 4 plus 1 more seat at the bar brbr- Access to outdoor dining in covered lounge, seats 6 brbr brbrBEDROOMS AND BATHROOMS: brbr- Master bedroom: king bed, wall-mounted TV and ensuite bathroom brbr- Master ensuite bathroom: walk-in shower and updated vanity brbr- Guest bedroom: queen bed, with work desk brbr- Guest bathroom: walk-in shower, vanity with big mirror brbr brbrEXTRA PERKS: brbr- Complimentary beach items provided: a couple of beach chairs, a beach wagon, beach umbrella and beach towels brbr brbrLOCAL FAVORITES: brbr- Siesta Key Village with shops, bars, and dining brbr- Siesta Key Beach brbr- Nearby outdoor activities like boating, paddleboarding, and kayaking brbr brbrIMPORTANT INFO: brbr- No smoking anywhere on property brbr- No parties or events, please respect the quiet residential neighborhood brbr- Pool heat optional at an extra cost brbr brbrMAKE MEMORIES THAT LAST A LIFETIME ON SIESTA KEY. BOOK YOUR PERFECT VACATION TODAY!brbrAll pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs.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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$712.14

/ Nightly

Private Vacation Home

Tidal Wave - In Siesta Key Village, Pet Friendly, Private Pool!

Siesta Key, Florida, United States

Tidal Wave – Spacious Siesta Key Village Retreat for Groups & Familiesbrbr Why You'll Love This HomebrWelcome to Tidal Wave, a thoughtfully combined duplex in the heart of Siesta Key Village, just two blocks from the powdery sands of Siesta Beach. With two fully private units—each with its own entrance, kitchen, and living space—this 4-bedroom, 4-bathroom property offers flexibility, space, and comfort for groups who want to be together without sacrificing privacy. Lounge by the heated pool, dine al fresco in the sunny backyard, or stroll into the Village for dining, shopping, and live music. This is the relaxed island lifestyle at its best.brbr ‍ ‍ Perfect ForbrMulti-generational families, multiple couples, or two families traveling together who want shared outdoor space and separate indoor retreats.brbr ️ Imagine This...brStart your morning with a quick walk to Siesta Beach for a swim, or rent bikes in the Village to explore the island. Head back to Tidal Wave for lunch prepped in one of the two fully equipped kitchens, then unwind by the pool in the private backyard. The kids can splash while adults relax with a drink under the palms. Later, grill up dinner, set the outdoor table, and enjoy a breezy evening meal together before heading into the Village for dessert or live music.brbr Where You'll SleepbrTidal Wave sleeps up to 12 guests comfortably:br• Bedroom 1: King Bed (1), Ensuite Bathroom with Walk-In Shower, TV (First Floor Unit)br• Bedroom 2: Twin Beds (2), Access to Hall Bathroom with Shower/Tub Combo, TV (First Floor Unit)br• Living Room 1: Full Sleeper Sofa (1), Access to Hall Bathroom (First Floor Unit)br• Bedroom 3: King Bed (1), Ensuite Bathroom with Walk-In Shower, TV (Second Floor Unit)br• Bedroom 4: Queen Bed (1), Access to Hall Bathroom with Shower/Tub Combo, TV (Second Floor Unit)br• Living Room 2: Full Sleeper Sofa (1), Access to Hall Bathroom (Second Floor Unit)brbr Explore the AreabrLocated just 0.2 miles from Siesta Beach and 0.1 miles from Siesta Key Village, Tidal Wave puts everything within walking distance. Enjoy fresh seafood, daiquiris, beach boutiques, live music, and water rentals all steps from your front door. A short drive brings you to downtown Sarasota, St. Armands Circle, or the Ringling Museum for off-island adventures.brbr Book Tidal Wave for Your Siesta Key GetawaybrWhether you're planning a family reunion or a beach vacation with friends, Tidal Wave gives you the flexibility to spread out and connect—all in the heart of Siesta Key. From morning swims to sunset strolls, this home is designed to make every day unforgettable.brbr Need to Know: Tidal Wave is a combined rental of two distinct units—one on the first floor (Low Tide) and one on the second (High Tide) - each with its own private entrance, kitchen, living room, and bathrooms. There is no interior connection between the two spaces, making it ideal for guests who want both privacy and shared time. Guests will enjoy access to a private backyard that includes a heated pool (available from November 15 through April 15), a lanai, and a barbecue area. The property is dog-friendly for small dogs under 25 lbs (pet fee applies). Free high-speed WiFi is provided throughout, along with starter packs of kitchen and toiletry essentials to make your arrival seamless. Each unit is also equipped with its own washer and dryer for added convenience.

4

Bed

4

Bath

12

Sleeps

Vacation Home Rentals By Owner In Siesta Key, FL

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$366.03

$298.23

$1838.17

$1074.69

$586.73

$549.87

$712.14

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