Home Vacation Villa Rentals By Owner In Siesta Key, FL

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Exceptional(19)

$393.44

/ Nightly
Villa

Island House Beach Resort V3

Siesta Key, Florida, United States

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrWelcome to paradise! This lovely and updated 2-bedroom, 2-bathroom villa features a private ensuite with a king bed and a guest room that features 2 twin beds. It is perfectly situated on the widest part of Crescent Beach, offering both privacy and comfort for your stay. Enjoy a beautifully updated, spacious living and dining area, a fully equipped kitchen, central A/C and heat, a screened lanai, and covered parking.brbrJust 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.brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!
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Bath 2

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Sleep 4

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$320.53

/ Nightly
Villa

Serene Villa with Community Amenities, Huge Pool, Steps from Private Beach

Siesta Key, Florida, United States

Welcome to Living the Dream Villa, a 2-bedroom Villa just a 5-minute walk from Siesta Key's breathtaking beaches. Ideal for families and friends, this inviting retreat offers both relaxation and nearby adventures in vibrant Siesta Key Village, filled with shops, restaurants, and nightlife.brbrHighlightsbr• Beach Access within 5-minute walkbr• Private Washer and Dryerbr• Work deskbr• Private Outdoor Spacebr• Community Shuffleboard, Pool, and Dockbr• Outdoor Seating and Grillbr• 5-minute walk to Siesta Key Breeze Trolleybr• Community Amenities:brbrAs a guest at Living the Dream Villa, you'll have access to the amenities of two associations! Enjoy shuffleboard and a scenic dock in Provincial Gardens, ideal for fishing and watching boats pass by. Just across the street, Aloha Kai offers a refreshing community pool and direct beach access, ensuring you have everything you need for an unforgettable getaway!brbrOutdoor Oasis:brYour private outdoor space includes an outdoor dining table and a plush outdoor seating area for enjoying the Gulf breeze.brBedroom Detailsbr-Primary Bedroom: Luxurious King bed, work desk, and ensuite bathroom with a walk-in showerbr-Second Bedroom: Two Full Size Beds, shares hall bath with shower-tub combobrExperience the perfect blend of relaxation and adventure at Living the Dream Villa, where every moment is an opportunity to unwind and explore. Book your stay today!brThis home is managed by Tropical SandsbrAccommodations, a Siesta Key and Sarasota property management company.brThis property does not allow pets of any kind.brWe do not accept reservations from anyone under 30 years of age. We do not allow persons under 30 to occupy a property unless accompanied by someone over 30 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details.br1 car 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.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 peace and quiet they expect in their own homes. Quiet hours are typically observed from 9PM to 8 AM, and we kindly ask that you avoid music outside, shouting, or any disruptive activity during these times. Thank you for helping maintain a peaceful environment for everyone.
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$297.52

/ Nightly
Villa

Horizons West Beautifully Remodeled 2 Bedroom Bayside Villa F-8

Siesta Key, Florida, United States

Discover your own slice of paradise in this brand new 100% fully renovated 2-bedroom, 2-bathroom villa, with vaulted ceilings and an open floor plan. This villa is located in the vibrant heart of Siesta Key. This charming retreat blends modern amenities with a prime location, ensuring an unforgettable vacation experience. Enjoy exclusive access to Horizons West Bayside Park just a few steps away where you can enjoy your morning coffee and evening libation while watching the dolphins ...and manatees swim by. You will also be able to enjoy the intercoastal waterway for boating and fishing. Private beach access to the pristine sands of the renowned Siesta Beach is only a short stroll away.brbrAs you enter this inviting villa, you'll be welcomed by an abundance of natural light and stylish new furnishings throughout. The kitchen is fully equipped with new appliances and everything you need to make a grilled cheese sandwich or a 7-course meal. brbrRetreat to the two elegantly designed bedrooms: a master suite featuring a king-sized bed and en-suite bathroom with an oversized rain shower. The second bedroom has a queen-sized bed with a spacious bath connected to the second bedroom. The villa is equipped with an 85 smart TV in living room and large screen smart TVs in both bedrooms for your entertainment needs. High-speed internet (WiFi) is also available.brbrAnother highlight of this beautiful villa is the covered patio, complete with a welcoming outdoor living space, Blackstone grill, and a Weber pellet grill. This villa also includes personal laundry facilities to enhance your convenience.brbrTake advantage of the two community pools, perfect for a refreshing dip or mingling with fellow vacationers. Hop on the free Trolley to explore local dining and shopping options in the Village (North) or Stickney Point (South).brbrWith a serene tree-lined street and tranquil atmosphere, this villa offers the ultimate blend of relaxation and comfort. Don't miss out on the chance to create cherished memories in this Florida gembook your stay today!brbrAmenities Include:brbr- BBQ Grill: Yesbrbr- washer dryer: Yesbrbr- Bay Side: Yesbrbr- Bed Size MBR: Kingbrbr- # of Baths: 2brbr- Bed Size Guest BR: Queenbrbr- Conf Line 1: Beautifully Redonebrbr- Conf line 2: Bayside Villabrbr- Conf Line 3: W/ Bay Viewbrbr
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Bath 2

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Sleep 5

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Exceptional(12)

$398.36

/ Nightly
Villa

Island House Beach Resort V9

Siesta Key, Florida, United States

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrWelcome to your coastal escape at Island House Beach Resort, perfectly located on the widest part of Crescent Beach. This lovely 2-bedroom, 2-bathroom villa offers comfort, space, and privacy for a relaxing stay.brbrThe villa features a primary ensuite bedroom with a king-size bed, a guest bedroom with two double beds, and a spacious living and dining area that includes a sofa bed, making it ideal for families or groups.brbrEnjoy a beautifully updated, fully equipped kitchen with modern appliances, a screened lanai perfect for morning coffee or evening relaxation, and covered parking for your convenience. The villa also includes three large flat-screen TVs and central heating and air conditioning for year-round comfort.brbrExperience the best of Siesta Key living with the privacy of your own villa and the amenities of a beautifully maintained beachfront resort just steps from the powdery white sands and turquoise waters of the Gulf of Mexico.brbrbrJust 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.brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!
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Bath 2

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Sleep 6

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Exceptional(27)

$407.76

/ Nightly
Villa

Island House Beach Resort V16

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 a queen and full bed, 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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Bath 1

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Sleep 5

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Exceptional(9)

$386.17

/ Nightly
Villa

Island House Beach Resort V29

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 twin beds, 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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Bath 1

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Sleep 4

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Exceptional(9)

$412.79

/ Nightly
Villa

Island House Beach Resort V34

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 twin beds, 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!
Bed 2

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Bath 1

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Sleep 4

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Exceptional(8)

$407.76

/ Nightly
Villa

Island House Beach Resort V2

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 beds and a sleeper sofa 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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Bath 2

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Sleep 6

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Exceptional(1)

$421.47

/ Nightly
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44 Premium Plus - Sandy Toes & Seaside Bliss

Siesta Key, Florida, United States

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