Home Vacation Rentals By Owner In Siesta Key, FL

Showing 360 Of 2077 Vacation Rentals
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Exceptional(6)

$602.61

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Condo

Beautiful Beach View Condo At Crystal Sands on Siesta Key!

Siesta Key, Florida, United States

Just 300 feet of powder white sand separate this unit from the crystal blue waters of the Gulf! This lovely, 2-bedroom 2-bathroom unit offers sleeping accommodations for 4. Inside, you will find a chef's kitchen with plenty of space to cook while being open to entertain guests as well. Relax on one of your private outdoor balconies or sit on the beach voted #1 in the USA! The unit is located in the tower, steps from one of the complex’s two heated pools and are closest to the private beach. All guests have access to the Crystal Sands private beach area located on Crescent Beach. Crescent Beach is one of three beaches located on Siesta Key and is known for being just as beautiful with fewer crowds than the more popular Siesta Key Public Beach. Pools are open from dawn till dusk daily. The beach access point is past the pool and guests will find beach chaises and chairs overlooking the crystal blue waters and soft white sand. brbrBedroom 1 – King brBedroom 2 – Two QueensbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Towels,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbrPlease Note: Golf-Carts are NOT allowed on property grounds.brbr*Minimum Age to Book: 27 br*Security Authorization Hold taken upon check-in. Amount: $1,000
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Exceptional(1)

$303.84

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Condo

Full Gulf Views! 2BR/2BR 4th floor Condo Steps To SK Beach

Siesta Key, Florida, United States

Welcome to Condo 4B at Crescent Royale Condominiums – Your Gulf-Front Escape on Siesta Key!brbrGet ready to unwind in paradise. This beautiful fourth-floor, gulf-front condo offers sweeping views of the Gulf from both the primary bedroom and your private screened-in lanai—perfect for morning coffee or sunset cocktails.brbrWith over 1,220 square feet of thoughtfully designed living space, this two-bedroom, two-bath residence comfortably accommodates up to four guests. The spacious primary bedroom features a king-size bed and stunning water views, while the guest bedroom offers two cozy twin beds. Two full bathrooms make getting ready easy and convenient.brbrThe fully equipped kitchen has everything you need, whether you’re preparing quick beach-day snacks or enjoying a relaxed family dinner at home.brbrStay connected and entertained with three TVs and complimentary high-speed Wi-Fi—ideal for streaming, remote work, or sharing your vacation memories.brbrStep outside and you’re just moments from world-famous Siesta Key Beach, known for its soft, powdery white quartz sand. When you’re ready to explore, hop on the free Village trolley or take a leisurely stroll to nearby shops, restaurants, and nightlife.brbrResort-Style Amenities Include:brbr• Heated gulf-front poolbr• Fitness centerbr• BBQ grilling areabr• Shuffleboard courtsbr• Friendly onsite managementbrbrWhether you’re seeking a peaceful retreat or an adventure-filled escape, Condo 4B is the perfect home base for your Siesta Key vacation. Book today and start making unforgettable beach memories!
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Exceptional(31)

$494.94

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Apartment

Island House Beach Resort 11N

Siesta Key, Florida, United States

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, along with a guest bedroom offering two twin beds. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!
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Exceptional(58)

$1192.01

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Private Vacation Home

Latitude Adjustment | Waterfront Home w/ Private Heated Pool! Walk to Siesta Village & Beach!

Siesta Key, Florida, United States

Latitude Adjustment | Private Heated Pool + Walk to Siesta Key Beachbrbr Why You'll Love This Homebr Step into Latitude Adjustment, a luxurious waterfront villa on Siesta Key's serene canals. With sun-drenched balconies, a private heated pool, and direct canal access, this home balances elegant design with effortless coastal living for families and friends alike.brbr ‍ ‍ Perfect Forbr Ideal for large families, groups of friends, or multi-generational gatherings seeking space, comfort, and a prime waterfront location.brbr ️ Imagine Thisbr Wake to the gentle lapping of canal waters and enjoy your morning coffee on one of two balconies overlooking the serene waterfront. Spend your days kayaking from your private dock, sunbathing by the heated pool, or strolling just 2 minutes to Siesta Key Beach. Evenings are for alfresco dining, sunset cocktails, or stargazing in your secluded backyard oasis. Every moment invites relaxation, connection, and fun.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Shared Bath, Ground Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, Main Floor, TVbr• Bedroom 3: King Bed, Ensuite Bath, Upper Floor, TV br• Bedroom 4: Two Full Beds, Ensuite Bath, Upper Floor, TVbrbr Explore the Areabr• Private canal access for kayaking and fishingbr• 0.1 miles to Siesta Key Beach – pristine white sands and turquoise waters (2-minute walk)br• 8-minute drive to Siesta Key Village – vibrant shops, restaurants, and entertainmentbr• Nearby local parks, boutiques, and waterfront dining within a short strollbr• Coastal energy and serene island vibe make every outing memorablebrbr⌛ Reserve With Confidence - Your stay includes our CottageClean™ program: 6-hour deep clean plus a 35-point inspection, ensuring a pristine, worry-free vacation.brbr Need to Know: This home is part of a duplex and may share a wall, floor, ceiling, or outdoor space with another unit. Your rental includes access to the private backyard and right side of the building. Pool heated from November 15 – April 15. This home has stairs. If any guest has difficulty, contact us for alternative accommodations.
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Exceptional(30)

$414.94

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Villa

Island House Beach Resort V5

Siesta Key, Florida, United States

Island House Beach Resort – Siesta Key, FloridabrVilla on Crescent BeachbrbrWelcome to paradise at the Island House Beach Resort! This beautiful 2-bedroom, 2-bathroom villa is perfectly situated on the widest stretch of Crescent Beach, one of Siesta Key’s most stunning and sought-after locations.brbrEnjoy the privacy and comfort of your own villa, complete with all the modern conveniences of home. The spacious primary suite features a king-size bed and a private ensuite bathroom, while the guest bedroom offers two full-size beds—perfect for family or friends. Relax in the large open-concept living and dining area, ideal for unwinding after a day at the beach or gathering together for meals and conversation.brbrThe fully equipped kitchen includes all major appliances, making meal prep a breeze. Relax in the screened lanai, unwind with your favorite shows on one of three large flat-screen TVs, or stay cool and comfortable with central heating and air conditioning. Covered parking is also included for your convenience.brbrExperience the best of Siesta Key with the space, comfort, and privacy of your own beachfront villa—just steps away from the white sands of Crescent Beach.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!
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Exceptional(30)

$634.29

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Apartment

Island House Beach Resort 13N

Siesta Key, Florida, United States

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, along with a guest bedroom offering two double beds. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!
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Sleep 6

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$1098.49

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Private Vacation Home

King beds-NO Bunks, Roku TV in bedrooms, Private Beach Access & Pool

Siesta Key, Florida, United States

Just a 5-minute walk to #1 beach in America!br-Heated pool*, Floats, Sun loungersbr-Equipped kitchen, drip & Keurig coffee makers, BBQ grillbr-King & queen size beds, NO BUNKS!!br-Garage parking, Close to trolley stopbr-Avoid crowded public beach with private access, beach wagon, chairs, umbrellas, & towels for guest usebrbrPLEASE READ LISTING THOROUGHLY TO ENSURE YOU HAVE ALL THE IMPORTATNT DETAILS!brbrDINING:br- Indoor dining table seating for 8br- Granite kitchen island seating for 3br- Upstairs on balcony outdoor table seating for 6br- Downstairs in pool area outdoor table seating for 6brbrLIVING ROOM:br- 75 Smart TV with Roku (for guests' protection)br- Access to huge balconybr- Board gamesbrbrBEDROOM 1br-King size bedbr- Ensuite Bath: walk in shower, dual vanities, soaking tubbr- Smart Roku TVbrbrBEDROOM 2br- King size bedbr- Ensuite Bath: walk in shower, single vanitybr- Blackout curtainsbr- Smart Roku TVbrbrBEDROOM 3br- King size bedbr- Ensuite Bath: walk in shower, single vanitybr- Blackout curtainsbr- Smart Roku TVbrbrBEDROOM 4br- Queen size bedbr- DeskbrbrBEDROOM 5 (downstairs suite)br- Queen size bedbr- Queen size sofa sleeper (made upon request)br- Ensuite bath: walk in shower, single vanitybr- Walk in closetbr- TV with Rokubr- Kitchenette: refrigerator, microwave, & sinkbr- Sliding glass doors to access pool areabrbrAVAILABLE UPON REQUEST:br- Twin rollaway bedbr- Pack N Playbr- HighchairbrbrStep into a world of luxury living at our 3,000+ square feet home. Everyone will have ample space to unwind; plus enjoy all the amenities you'll need to have a relaxing & memorable stay. brbrThis spacious 5-bedroom, 4.5-bath home offers accommodations for up to 10 guests comfortably. It is a two-level retreat that features an elevator for easy access between your two levels, making it the perfect choice for travelers of all ages & abilities.brbrOnly minutes away from incredible downtown Sarasota & St. Armand's Square!! brAnd is centrally located on Siesta Key Island with the Publix grocery store, Siesta Key Village, & 7-Eleven less than 2 miles from the property.brbrIMPORTANT HOUSE INFO & RULESbrbr** NO PARTIES OR LARGE GATHERINGS: Any parties, events, or gatherings that EXCEED the number of guests on the reservation are STRICTLY PROHIBITED! Violations will result in an immediate $1,000 fee & possible removal from the property without refund. brbr** NO THIRD-PARTY RESERVATIONS: Person making the reservation MUST be present during the stay. We do not allow making a reservation on behalf of a friend, family member or co-worker. Please have the person who is staying book themselves. brbr**OCCUPANCY: Only the number of guests listed in your reservation are allowed on the property at any time. Unauthorized guests may result in additional charges & cancellation of your reservation. brbr** NO SMOKING: There is NO SMOKING (this includes cigarettes, cigars, vaping & any controlled substances (including marijuana) INSIDE & OUTSIDE on the property. Any evidence of smoking on the property, a minimum $500 fee will be charged.brbr** PET POLICY: This home is NOT pet friendly. We make no exception to the rule no matter the size, type or behavior of animal.brbr** PARKING (FOUR CAR MAX): Two midsize vehicles or smaller can park in the (empty) garage, with two additional parking spots on side of house to accommodate 2 midsize vehiclesbrNOTE: Vehicles that are larger than midsize, please contact to discuss parking options.brbr** QUIET HOURS: Please respect our neighbors by observing quiet hours from 10:00 PM to 8:00 AM. All of our communities have noise ordinances requiring guests to keep noise to a minimum, specifically after 10 PM and before 8 AM. Law enforcement officials may be summoned to the property if you are deemed to be in violation of these ordinances. You may also be subject to a fine.brbr** EARLY LUGGAGE DROP OFF: Our team needs this time to prepare the home uninterrupted. Upon booking, we can offer recommendations to where to leave your luggage while you wait, should you have an early flight.brbr** POOL HEATING: The pool is heated from October through February ONLY.brbr**We STRONGLY RECOMMEND purchasing travel insurance AHEAD of your stay.**brbrbrThis property is the entire 2nd floor & half of the ground floor. brbrThere are 3 exterior security cameras that record when someone enters the property from the driveaway & side of the home that runs along the street. Used to primarily protect the property, & to monitor weather situations.brbrView a video tour of the property here for more details: https://youtu.be/pibCeOe3lSA
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Exceptional(6)

$551.82

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Apartment

Gertrude's Siesta | Private Patio, Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!

Siesta Key, Florida, United States

Kaia's Pool SidebrNewly remodeled with private patio, pool and jacuzzi, just 1-minute walk to Siesta Key beach! Poolside lounging and grilling, sunsets, sandbars, and on reef snorkeling and paddling. Just 4-min walk to shopping dining bars and live music. Book your Siesta Key vacation rental getaway now!brbrWhat Guests Lovebr∙ Private Patio – private patio off master, palm and pool views!br∙ Beaches 1-min walk to award winning beaches, white sand, calm waterbr∙ Relaxing private balcony and patio with dining and loungingbr∙ Pool beautiful heated pool with tropical plants just 1-minute walkbr∙ Reef Snorkeling 70-yard walk to Point of Rocksbr∙ The Food 12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 milesbr∙ Activities Boat bike jet-ski sport-fishing tours, marina and rentals 7-min awaybr∙ Sunsets 1-minute walk to best sunsets and whatever comes nextbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories access Siesta Key s top attractions and beaches guaranteed fun for allbrbrThe BeachbrAccess to two private Siesta Key beaches. With no public parking nearby, this cove is one of Siesta s more exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.brbrThe LocationbrNo car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 4-minutes two 12 bars and restaurants. Walk 7-minutes to Siesta s top eco-adventures boat, bike, jet-ski, and fishing tours. Prefer to relax Sunbathe at the beach, nap by the pool or enjoy Siesta s top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.brbrReef SnorkelingbrSiesta Key is already paradise now add one of the Gulf Coasts best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you ll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.brbrBedroom DetailsbrThis unit is two flights up with no one above it. There is a king bedroom, a queen bedroom and a sectional sofa. Need more space We can get you an additional unit nearby.brbrBeach Gear ProvidedbrWe provide beach towels and the resort supplies chairs and umbrellas. If you don t have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt s a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.
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Exceptional(65)

$223.04

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Condo

Midnight Cove II 710F: Ground Floor Siesta Key Beach Condo

Siesta Key, Florida, United States

Welcome to Midnight Cove II 710F! This beautifully renovated 1st-floor condo offers 2 bedrooms and 2 bathrooms, making it the perfect getaway for families, friends, or couples seeking a memorable vacation on Siesta Key. Located just steps from the sparkling waters of Siesta Beach and our dedicated private beach access, this charming unit is ideal for soaking up the Florida sun.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• CornholebrbrThe spacious living area features cute beach decor and an extended eating area that's perfect for family meals. The primary bedroom boasts a cozy queen bed, while the guest bedroom offers two twin beds, accommodating up to six guests comfortably with the queen sleeper sofa in the living room. Enjoy the peaceful ambiance of the screened-in lanai, perfect for relaxation after a day of adventure.brbrMidnight 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). brbrBook your stay at Midnight Cove II today and enjoy all the beauty and charm that Siesta Key has to offer! Create unforgettable memories at one of Florida’s top vacation destinations!
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Exceptional(140)

$367.25

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Condo

Crescent Arms Luxurious Beach Condo on Siesta Key 605 South with gulf view

Siesta Key, Florida, United States

Enjoy your private beach at Crescent Arm. Beach chairs set up for you every morning and brought back to the seawall every evening for free. Umbrella rental service among other things is available right on the beach.brbrSaturday to Saturday rental only. No pets/smoking.brbrFreshly painted this May 2025, new linens, curtains. brbrCrescent Arm condo 605S in South building with a gulf view from side of lanai. Keyless entry. I also own/rent 604S next door (#9467797) which is great for family/friend reunions!brbr25 steps to the quiet, sugar sand private beach with chairs provided for relaxation. Perfect area for families as the sandy is cool to the touch and the water is usually calm and clear. No street to cross to get to the beach!brbrFree Secured Wi-Fi. Computer desk in guest bedroom.br brBeach towels, sand toys, beach chairs, cooler and beach umbrella available for use. DVD movies, games and books to borrow. Everything you need to relax and enjoy is provided. Pack your lotion, clothes and sunglasses and sit back and enjoy! brbrBamboo floors throughout unit.brbrDecorated in a tropical Tommy Bahama décor and immaculately clean. brbrEach bedroom has their own private bathroom, flat screen TV, ceiling fan and private door to the lanai.brbrLarge flat screen TV in the family room with DVD player and movies provided and door to relaxing lanai.brbrHeated pool, shower and bathrooms at pool area.brbrSiesta Breeze trolley will take you up and down the key for free! Walking distance to shopping, restaurants or stores. Daiquiri Deck on Stickney Point within walking distance.brbrBusch Gardens, Tampa Bay Rays and Bucs are only one hour away. Disney is two hours away. The Atlanta Braves new spring training in North Port is only 35 minutes away.brbrSpring training games are in Sarasota, Tampa and Ft. Myers, no further than a one-hour drive! brbrMany cultural attractions are available: Ringling Museum, the theater, Marie Selby Gardens, the Mote Aquarium, ghost tours, breweries and more.brbrNew Breeze route from SRQ to the key! Plenty of ways to get around without needing a car. If you bring a car, there is one covered, reserved spot for your car.brbrTwo grills are available for your outdoor cooking needs.brbrLanai has a side Gulf View with couch, two chairs and 3 side tables for a relaxing nap, reading a book or having a drink to unwind after a day at the beach. Beautiful breeze!!
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Exceptional(10)

$172.25

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Condo

Walk to Siesta Key Beach | Pet Friendly | 2nd Floor Condo | Heated Pool | Rent a Boat Dock

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrCoastal Comfort Near Siesta Key Beach | White Sands Village, Sarasota brbr brbrEnjoy automatic discounts based on your stay length—no codes needed! The price you see already includes your savings. brbr brbrThis lovely 2nd-floor, 2-bedroom, 2-bathroom condo at White Sands Village is perfectly located for your next Siesta Key getaway. Just a 10-minute walk or 2-minute drive to Siesta Key Beach, one of the top beaches in the U.S., this property offers the ideal balance of comfort and convenience. Guests can also enjoy community amenities such as a heated pool and BBQ grills within the complex. brbr brbrHighlights brbr- Spacious 2nd-floor condo (stairs only – no elevators) brbr- Screened lanai overlooking the complex grounds brbr- Smart TV and free Wi-Fi brbr- Assigned covered parking brbr- Dog-friendly (under 25 lbs) with prior approval and non-refundable fee brbr-Communal laundry facilities brbr-Two beach chairs and an umbrella included brbr brbrBedrooms & Bathrooms brbr-Master Bedroom brbr-Queen bed brbr-Ensuite bathroom with tub/shower combo and toilet brbr-Flat-screen TV brbr-Guest Bedroom brbr-Two twin beds brbr-Dresser and ample natural light brbr-Hall Bathroom brbr-Walk-in shower and toilet brbr brbrKitchen & Living brbr-The kitchen is fully equipped with everything you need for a comfortable stay: brbr-Full-size appliances, dishes, silverware, pots, and pans brbr-Open layout to the dining and living areas brbr-Bright and comfortable décor ideal for relaxing after a day at the beach brbr brbrCommunity Perks – White Sands Village brbr-Heated community pool brbr-BBQ grills for guest use brbr-Lush, well-kept grounds with tropical landscaping brbr-Assigned covered parking brbr-Conveniently located just across from Siesta Key Beach brbr brbrPet Policy brbr-This property allows small, well-behaved dogs under 25 lbs with prior approval and a non-refundable $300 pet fee (plus tax and processing) per pet. brbr-No cats allowed per HOA rules brbr-Guests must pick up after their pets brbr-HOA approval required prior to arrival brbr brbrImportant Information brbr-HOA application required for all guests brbr-Pipe replacement project scheduled to begin around May 1, 2024 (completion date TBD) brbr-Ask before booking to confirm if your vehicle is allowed (some oversized or commercial vehicles are restricted) brbr-Xplorie activities package not available for bookings of 25 days or longer brbr-Communal laundry facilities available (no in-unit washer/dryer) brbr brbrExclusive Guest Perks brbr-Book with us and enjoy Xplorie’s Free Daily Activities, including: brbr-One free bike rental, kayak rental, dolphin cruise tour, or admission to the Ringling Museum each day of your stay brbr-Free round-trip airport transportation for up to 3 passengers (SRQ or TPA) with advance reservation — please tip your driver brbr-Activities are non-cumulative, non-transferable, and subject to availability. brbr brbrLocation brbr-White Sands Village Condominiums brbr-Siesta Key, FL brbr-Just across the street from Siesta Key Beach brbr-Close to Siesta Key Village dining, shopping, and entertainment brbr-Short drive to downtown Sarasota, golf, marinas, and morebrbrWe 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.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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Exceptional(1)

$322.2

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Condo

Enjoy Two Pools, Tennis Courts, and Siesta Key Beach Access

Siesta Key, Florida, United States

Harbor Towers 420 by Tropical Sands Accommodations brbrExperience the perfect Gulf Coast getaway at Harbor Towers 420, a charming bayfront condo ideally located just a short walk from Siesta Key Beach. This bright and inviting two-bedroom, two-bathroom residence offers stunning views of Siesta Key Beach and the Intracoastal Waterway. With access to two heated pools, tennis courts, a fitness center, and a marina, this condo is perfect for families or small groups seeking relaxation and outdoor fun in the heart of Siesta Key. Just a short walk or trolley ride to Siesta Key Village provides easy access to shopping, dining, and local attractions to explore throughout your stay! brbrHighlights br• 7-minute walk to Siesta Key Beach br• 2 Bedroom / 2 Bathroom br• 1 King, 1 Queen br• Beach chairs (4) and cart included  br• Two heated community pools   br• Tennis courts and fitness center br• Shared grilling area br• Marina onsite for boat rentals or water adventures  br• 1 Parking spot  br• Short stroll to Siesta Key Village for shopping and dining  br• 3-night minimum stay communitybr brEnjoy resort style living with access to two heated pools, tennis courts, a fitness center, and a marina. The outdoor grilling patio makes hosting barbecues effortless, while the scenic water views support a relaxing vacation atmosphere. Inside, the bright living space with comfortable furnishings provides a peaceful retreat after exploring Siesta Key’s sandy shores a short stroll away. br brThe open concept living area offers a welcoming space with plush seating, a large flat screen TV, and tropical decor. The fully equipped kitchen features all essentials for cooking meals or preparing snacks, connecting seamlessly to a cozy dining area ideal for family gatherings. Large windows and sliding doors extend to the screened balcony overlooking the water and pools, blending indoor comfort with outdoor ambiance.br brThe primary bedroom features a king-sized bed and an ensuite bathroom with a walk-in shower, creating a luxurious master retreat. The second bedroom offers a queen-sized bed with its own ensuite bathroom with a walk-in shower. Each bedroom is a calming ocean inspired space, ensuring restful nights after days filled with sun and fun. brbrRoom Details br• Primary Bedroom: King bed, ensuite with walk-in shower  br• Second Bedroom: Queen bed, ensuite with walk-in shower brbrGuests enjoy a shared coin laundry facility, access to the pools, tennis courts, fitness center, and a scenic water setting. The marina provides easy access for boat rentals or watercraft adventures. Located just minutes from Siesta Key Beach and village attractions, Harbor Towers 420 offers a perfect blend of relaxation and activity to create a memorable Gulf Coast escape. br brBook your stay at Harbor Towers 420 today and immerse yourself in the sun, sand, and serenity of Siesta Key. Relax by the pools, explore nearby beaches, or discover local shopping and dining in Siesta Key Village. Whether on a family vacation, romantic retreat, or small group getaway, this condo provides everything needed for an unforgettable Gulf Coast experience. Reserve your dates now and start your island adventure! br brbr- brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis property does not allow pets of any kind. brbr1 car maximum is 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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Exceptional(4)

$3035.66

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Private Vacation Home

Luxury Villa*Pool*Hot Tub*Dolphins*Close to Beach

Siesta Key, Florida, United States

Livin` the Dream — Luxury Waterfront Villa with Pool, Spa & Dolphins at Your DoorstepbrWake up to the soft sounds of waves and shimmering sunlight reflecting off the water. Sea Breeze Retreat is a luxury oasis on Siesta Key, where serenity meets sophistication. Watch dolphins glide by from your private dock, enjoy sunset dips in the heated pool and hot tub, and unwind in total privacy surrounded by lush tropical beauty. This is coastal living at its finest.brbr The SpacebrStep into a world of refined comfort and relaxed elegance. Every corner of this designer villa has been curated for a seamless indoor–outdoor experience.br ️ Bedrooms: 6 spacious suites featuring premium linens and smart TVs throughout.brMaster Suite: King bed with ensuite bathbrJunior Master Suite: King bed with ensuite bathbrGuest Room 1: Queen bedbrGuest Room 2: Queen bedbrBunk Room: full-over-full bunk bed Plus Queen bedbrGuest Room 3: Full bedbr Bathrooms: 4 luxurious, spa-inspired full baths with premium finishes, designer tile, and modern amenities.br Chef’s Kitchen: Wolf & Sub-Zero appliances, quartz countertops, and a massive island perfect for gathering.br ️ Living Area: Soaring ceilings, panoramic windows, and a cozy fireplace overlooking the pool and bay.br Workspace: High-speed Wi-Fi and a dedicated desk area for remote work or creative escapes.br________________________________________br Outdoor ParadisebrYour private resort awaits — designed for quiet mornings and unforgettable evenings.br Heated Pool & Hot Tub: Relax beneath swaying palms or take a midnight soak under the stars.br Nature Views: Spot dolphins playing in the canal, fish jumping at dusk, and manatee gliding by from the dock. br Outdoor Lounge: Plush seating, dining area for 10, and a built-in grill for sunset barbecues.br Private Dock: Perfect for kayaking, paddleboarding, fishing, or simply soaking in the serenity of the water. This property is a boater`s dream! Get picked up from your private dock by one of our partner charter boats for a day of cruising or sport fishing all while exploring the azure waters of Siesta Key. br Sun Deck: Chase the Florida sun or curl up with a book in the shade — your choice.br________________________________________br LocationbrTucked away in the peaceful Siesta Cove neighborhood, yet just minutes from everything:br ‍♀️ The home is a short walk/golf cart ride to Siesta Key the #1 beach in America. br ️ Close to Siesta Key Village — coastal restaurants, cafés, and boutiques.br ‍♂️ Adventure Ready: Paddleboards, kayaks, and beach gear available.br Near Sarasota’s Culture: Art galleries, theaters, fine dining — a short drive away.br________________________________________br⭐ Why Guests Love ItbrGuests consistently describe Sea Breeze Retreat as “serene, spacious, and soul-restoring.”brIt’s where luxury meets tranquility — a home that feels both indulgent and intimate.brMost guests say their favorite moments are sipping coffee while watching dolphins or grilling fresh-caught fish as the sun sets over Siesta Key.br________________________________________br ️ Amenitiesbr✅ Heated Pool & Hot Tubbr✅ Private Boat Dock & Water Viewsbr✅ Smart TVs in Every Roombr✅ Gourmet Kitchen w/ Luxury Appliancesbr✅ High-Speed Wi-Fi & Workspacebr✅ Beach Gear & Towels Providedbr✅ In-Home Laundrybr✅ Private Parking for up to 6 Carsbr✅Culligan Whole House Water Purification Systembr✅Pool Table / Ping Pong / Bagsbr✅Paddle Boardsbr✅Basketball Netbr✅Poker Tablebr✅Spike Ballbr________________________________________br Booking Detailsbr• Check-in: After 4 PM | Check-out: By 11 AMbr• No smokingbr• Small pets considered with Pet Fee (with approval)brbr** Note - Per Sarasota county ordinance, there is a 1 rental per 30 day period. brbr Final NotebrLuxury homes like this are rare on Siesta Key. Livin` the Dream offers not just a place to stay — but a place to breathe, reconnect, and watch nature’s beauty unfold right outside your door.brBook your stay today and experience the serene magic of Siesta Key— where the pool sparkles, dolphins dance, and every sunset feels like a dream. brbrGuests can enter the property via a keypad lock on the front door. We will provide an access code and check-in instructions before arrival.brbrMonthly or longer stays require discounted house cleaning every 2 weeks paid by guest. Pets welcome. Pets need pre-approval. $25 per day per pet. Please keep pets off furniture and crate your furry friends if you are planning on leaving them unattended.br• Must upload Government ID upon Booking if not already completed.br• No Smoking Anywhere in the home or near home openings. Smoking anywhere in home will result in a $500 remediation fee. Smoking is permitted outdoors. $50 cleaning fee if butts found on property.br• Quiet Hours between 10 pm and 8 am. Siesta Key has a noise ordinance program that is enforced by local law enforcement. We ask guests to please be considerate of neighbors and mindful of noise levels . Ignoring these noise ordinances can result in fines and termination of the rental agreement. . br• Check-in Any time After 4 PM. Check out 11 AM.br* We allow up to 6 cars parked on the driveway. You are not allowed to park on the street or you will get a ticket. Absolutely no RV or trailer parking on Driveway. No parking on lawn.br• If you have any needs or issues, you agree to message us through Airbnbbr• No parties! br• Do not have more guest than stated in your reservationbr• No Loud musicbr• There is 1 garage openers to use as a convenience. You will find them in the kitchen. Please return these openers to the kitchen. There is a $125.00 per remote if lost or not returned.br• We are not responsible or liable for any accidents, injuries or illness that occur while on the premises. We are not responsible for the loss of personal belongings or valuables during your stay. We cannot be responsible for any items left behind.br• There will be a minimum handling fee of $50, plus cost of shipping for anything you request being returned. Requests must be made with 7 days. Outside of 7 days, items may be donated at the sole discretion of the host.br• Mail service not supported. All packages will be rejected. We suggest guests that require mail delivery set up a temporary mailbox at the UPS Store or USPSbr• Security Deposit - any guest found to have damaged the home may be held liable and charged accordingly. Additionally, any guests found to have more people staying overnight at the property, or found having a party or event may be forced to forfeit the security deposit or may be asked to leave the premises. The authorities may also be contacted if necessary.br• 24-hour outdoor camera and remote security team monitoring
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$396.04

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Villa

Island House Beach Resort V38

Siesta Key, Florida, United States

House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin beds and a sofa bed in the living area, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!brIsland
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$398.36

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Villa

Island House Beach Resort V27

Siesta Key, Florida, United States

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twins and a sofa bed in the living area, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!
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$273.41

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Villa

Jamaica Royale #40 - 3 Heated Pools on the Beach - One Ocean-Side!

Siesta Key, Florida, United States

Welcome to Jamaica Royale Villa #40! - An Ocean and Beach-front complex on Siesta Key. Private Beach, 3 heated community Swimming pools: one being Ocean-Side! the other two just steps from the lanai sliding glass doors. Ground-Floor, park in front of unit, gas grills, outdoor shower. Located on #1 rated Crescent Beach, Jamaica Royale is less than a 1/4 mile to the Siesta Key Public Beach, less than a mile to Siesta Key Village.brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrThe spacebr• Rooms: Living room, open kitchen, master bedroombr• Bed Configuration: (2) Queen beds in master bedroombr• Sleeper Sofa: Yesbr• Dining Seating: Table with (4) chairsbr• Kitchen: Fully furnished, stove, fridge, freezer, micro, dishwasher, blender, coffee maker, toasterbr• Washer / Dryer: Small stacked washer / dryer within condobr• Bathroom: Shared access, walk-in shower, all tilebr• Linens: All bath and beach towels are provided. Sheets, blankets, pillows are also providedbr• Flooring: Ceramic tile throughoutbr• Property Upgrades: Great location close to Villa pool, park your vehicle (3) steps from front doorbrbr--------------------------------------------------brProperty Amenitiesbr--------------------------------------------------br• Coffee Maker: Mr. Coffee - standard dripbr• Ceiling Fans: (2) - Living room, master bedroombr• Iron and Board: Yesbrbr--------------------------------------------------brInternet and Entertainmentbr--------------------------------------------------br• Local Phone: No local phone providedbr• Internet: Yes, High-speed internet provided at no additional costbr• Cable TV Provided: Yes, Frontier FIOSbr• Pay-Per-View Avail: No, Frontier On-Demand movies available at no additional costbr• TV Configuration: (3) LED flat screen TVs; (1) in living room, (1) in each bedroombrbr--------------------------------------------------brLocation and Beach Related Informationbr--------------------------------------------------br• Physical Location: Villas, North Rowbr• Distance To Beach: Short walk to the beach, less than (5) minutesbr• View From Location: Garden View; just a few steps from Pool #3, Shuffle Board, Front Officebr• Lanai or Patio: Yes, private patio with lounge chairsbr• Parking: (1) Assigned covered parking space directly in front of Villa - guest parking availablebr• Beach Chairs: Chairs and loungers are provided at beach and pools at no additional costbr• Beach Toys: Beach toys are not provided - clients sometimes purchase and leave for othersbr• Cooler Provided: Yes, small (18) quart will hold about (18) cans or bottlesbr• Umbrella Provided: Yesbrbr-----------------------------------------------------------brSTARTER SUPPLIES PROVIDED INTENDEDbrTo Buy Time Before Purchase Quantitybr-----------------------------------------------------------brKitchen and Laundrybr• (1) Roll of paper towelsbr• (1) Small bottle dish washing liquidbr• (1) Small bottle cleaning liquidbr• (1) Scouring padbr• (2) Dishwasher tabletsbr• (2) Plastic trash bags in each trash canbr• Plastic trash bagsbr• (1) Load washer detergent IF property has washerbrbrBathroomsbr• (2) Rolls of toilet paperbr• (1) Small bottle of shampoobr• (1) Small bar of soap at each sinkbr• (1) Hair dryerbr• Bath towels, hand towels and washclothsbr• Guests are expected to wash all towels prior tobr• Departure in properties that have washing machinebr• Bedroomsbr• All Linens: Sheets, pillowcases and pillows, blanketsbr• Our cleaning company strips beds and launders linensbr• Beach Relatedbr• Beach towelsbr• Small coolerbrbr--------------------------------------------------brClosest Airports to Siesta Keybr--------------------------------------------------br• (SRQ) Sarasota - (20) Minutesbr• (PIE) St. Petersburg - (50) Minutesbr• (PGD) Punta Gorda- (55) Minutesbr• (TPA) Tampa - (60) Minutesbr• (RSW) Ft. Myers - (90) Minutesbr• (MCO) Orlando - (2) Hoursbr• (SFB) Sanford/Orlando - (2) HoursbrbrbrOther things to notebr• Minimum Rental Age: (25) years oldbr• Pet Policy: No Pets Permitted
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