Vacation Villa Rentals By Owner In Siesta Key, FL

If the beach is calling your name, Villa 29 at Aloha Kai is the perfect retreat. Whether you’re grabbing a towel and heading to the shore or curling up with a good book by the pool, you’ll find plenty of sunshine and tranquility to enjoy. Unwind on your screened porch or sink into the comfort of a king-size bed as you rest and recharge. For your convenience, this villa also includes a washer and dryer. Located on Siesta Key, a beloved barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach—consistently ranked the number one beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s top vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and unforgettable sunsets. Aloha Kai completes the experience with shaded beach pavilions and the largest pool on Siesta Key, making it the ideal setting for a relaxed and memorable beach vacation.

Villa 29 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$366.14

Renew your spirit and indulge in a beach getaway that celebrates the simple pleasures of life at Villa 30 at Aloha Kai. Unplug, put your feet up, and embrace the tranquility—whether it’s a leisurely walk on the beach, a refreshing swim in the pool, reading on the front porch, or grilling on the back patio. Your only task is to enjoy the day exactly as you please. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz beaches and emerald green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most breathtaking sunsets you’ll ever see. Aloha Kai provides the perfect setting for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

Villa 30 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$380.26

Early risers and night owls can live in harmony at Villa 50 at Aloha Kai, where the thoughtful layout features bedrooms upstairs and a convenient bathroom downstairs. This beautifully renovated villa boasts new flooring, an updated kitchen with stainless steel appliances, granite countertops, and modern bathrooms. Whether you're enjoying a meal in the spacious dining room or dining al fresco on the back patio, comfort and style surround you. Located on Siesta Key—a beloved barrier island on Florida’s West Coast—Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s top vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the sparkling Gulf of Mexico offer soul-soothing walks and unforgettable sunsets. Aloha Kai provides the perfect setting for a laid-back beach vacation, with shaded beach pavilions and the largest pool on Siesta Key waiting for you to unwind and relax.

Villa 50 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

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Bath

Sleeps

$401.12

Villa 45 at Aloha Kai is a newly renovated, light-filled coastal retreat featuring an updated white kitchen that perfectly complements its bright, beachy furnishings, with a 5-night minimum stay required. Whether you prefer a refreshing swim in the Gulf of Mexico or a relaxing afternoon by the pool, the choice is yours. With a king in the main bedroom and one twin and one double in the guest bedroom, this villa comfortably accommodates guests, making it ideal for a family visit. The front porch and back patio extend your living space, offering the perfect spots to unwind and soak in the island atmosphere. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach—rated the number one beach in the continental United States. Known for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico enchant even the most seasoned travelers, providing the perfect backdrop for soul-soothing walks and breathtaking sunsets. Aloha Kai invites you to embrace the laid-back beach lifestyle—whether you’re lounging under shaded pavilions or enjoying the largest pool on Siesta Key.

Villa 45 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$420.72

Villa 54 at Aloha Kai is your ideal beach retreat, spacious, sun-filled, and designed for total relaxation. This corner villa features an open floor plan with abundant natural light, custom cabinetry, and thoughtful upgrades throughout. The updated kitchen includes stainless steel appliances and is fully equipped to make meal prep easy, while the in-unit washer and dryer add everyday convenience during your stay. Enjoy the comfort of an Insta-hot water heater, a walk-in shower, a half bath in the master bedroom, and three TVs for your entertainment. Whether you're lounging on the porch, soaking up the sun by the pool, or taking a short stroll to the beach, this is your place to unwind at your own pace. Located within the gated, family-friendly Aloha Kai community on Siesta Key, Florida’s beloved barrier island, Villa 54 is just steps from world-renowned Crescent Beach, famous for its powdery white quartz sand and emerald-green waters. Frequently ranked the number one beach in the continental United States, this breathtaking stretch of shoreline offers soul-soothing walks and unforgettable sunsets. Aloha Kai completes your vacation experience with shaded beach pavilions and the largest pool on Siesta Key. Whether you're seeking a peaceful escape or a fun-filled getaway, Villa 54 offers the perfect setting for creating lasting memories.

Villa 54 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$426.58

Villa 38 at Aloha Kai is a fully renovated retreat offering a spacious living area that opens onto an enclosed porch—perfect for enjoying your morning coffee, with a 5-night minimum stay required. Its unique design features beamed ceilings and eclectic furnishings, creating a charming beach bungalow atmosphere. The fully equipped kitchen has everything you need to prepare meals to enjoy on the patio, and a convenient walk-in shower adds to your comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico impress even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the perfect setting for a laid-back beach vacation, inviting you to relax under shaded beach pavilions or by the largest pool on Siesta Key.

Villa 38 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$547.37

Welcome to Villa #27, your home away from home on beautiful Crescent Beach, Siesta Key. As one of Aloha Kai’s closest villas to the Gulf of Mexico, you are just steps away from the top-rated beach in the United States. The villa’s décor is comfy and casual, featuring two sofas, a dining table that seats six, and an open kitchen—perfect for relaxing evenings in. Kick back and enjoy a late-night movie with all your favorite channels and streaming apps available on the TV. Villa #27 offers two bedrooms, two bathrooms, and a spacious family room larger than most at Aloha Kai. The fully equipped kitchen and washer/dryer add to the convenience. One bedroom has a king-size bed, while the second features a queen bed with a twin trundle and a pull-out sofa, comfortably accommodating up to five guests. Outside, you’ll find a private outdoor shower, a charcoal grill, and a small front patio with two Adirondack chairs—ideal for savoring an evening cocktail. The villa includes one parking space, with room for a second car in the driveway if needed. We hope you enjoy your unforgettable vacation on Siesta Key!

Villa 27 - Premium Plus - W&D Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$561.89

Villa 52N at Aloha Kai offers the perfect escape for your next beach vacation, featuring three comfortable bedrooms plus a murphy bed and the convenience of an in-unit washer and dryer. Located on Siesta Key—a popular barrier island along Florida’s breathtaking West Coast—this villa is part of Aloha Kai, a family-friendly, gated resort community nestled in the heart of Crescent Beach, consistently ranked the number one beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s most sought-after vacation destinations. The stunning three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico create an unforgettable backdrop for peaceful walks and magnificent sunsets. Whether you prefer lounging under shaded beach pavilions or unwinding by the largest pool on Siesta Key, Aloha Kai provides the ideal setting for a relaxed, sun-soaked getaway. The top balcony is closed off due to damages.

Villa 52N - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$593.8

Light, bright, and beachy—Villa 56 at Aloha Kai welcomes you with its retro charm and casual coastal elegance. The inviting interior is enhanced by an updated bath that offers a spa-like retreat, perfect for unwinding after a sun-soaked day at the beach or an afternoon exploring the shops and restaurants in town. In the evening, enjoy a peaceful sunset stroll along the shoreline, then return to your villa to relax on the porch with your favorite drink in hand, soaking in the balmy coastal breeze. For added convenience, the villa includes a washer and dryer. Located on Siesta Key, a beloved barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community in the heart of Crescent Beach—ranked the number one beach in the continental United States. Known for its powdery white quartz sand and shimmering emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico create the perfect backdrop for soul-soothing walks and unforgettable sunsets. Aloha Kai completes the experience with shaded beach pavilions and the largest pool on Siesta Key, offering the ultimate setting for a relaxed, laid-back beach vacation.

Villa 56 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$600.41

Villa 61 at Aloha Kai warmly welcomes you with its cheerful coastal décor, designed to help you forget your worries and simply be happy. Its casual, comfortable style will make you feel right at home, while offering the luxury of both beach and pool access—you’ll just have to decide which you prefer. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai provides the perfect backdrop for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

Villa 61 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$605.67

Let’s all go to the beach! Villa 52S at Aloha Kai is a spacious and bright 3-bedroom, 2-bath getaway with plenty of room for everyone to relax and enjoy. The large, open kitchen is perfect for gathering with friends and family to prepare drinks, snacks, or full meals to enjoy in the dining room or on your private rooftop patio. For added convenience, this villa also includes a washer and dryer. After a day in the sun, kick back in the comfortable, beach-themed living room and enjoy a movie night on the brand-new 65 flat-screen TV. With both a tub and a walk-in shower, this villa offers the comfort and flexibility of home—just steps from the sand. Located on Siesta Key, a beloved barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community tucked into the heart of Crescent Beach—ranked the number one beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear, calm waters of the Gulf of Mexico provide the perfect setting for peaceful walks and unforgettable sunsets. Aloha Kai completes the experience with shaded beach pavilions and the largest pool on Siesta Key, offering the ideal setting for a laid-back, sun-soaked island escape.

Villa 52S - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$701.94

Villa 22 at Aloha Kai is where memories are made while spending time at the beach with family and friends, offering the perfect spacious setting. Its open floor plan fosters conversation and connection, encouraging moments away from screens. After a day of sunshine and sandy toes, gather in the updated kitchen, featuring a casual dining bar designed to invite everyone to join in meal preparation. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the ideal location for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

Villa 22 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$438.96

Paradise is found at Villa 39 at Aloha Kai! Meticulously renovated, this villa stands out with its beamed ceilings and open floor plan, creating a cozy and inviting atmosphere from the moment you step inside this exceptional beach retreat. The primary bedroom features relaxing coastal decor and a spa-like private bath, while guests will feel equally comfortable in the thoughtfully designed living spaces. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald green waters, Siesta Key is one of Florida’s premier vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you will ever see. Aloha Kai is the perfect location for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

Villa 39 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$460.69

Enjoy a relaxing getaway in Villa 3 at Aloha Kai, a cozy beach villa beautifully decorated with casual coastal charm. The screened porch provides the perfect spot for morning coffee, unwinding with a good book, or entertaining guests in the evening with a meal or cocktail. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key stands as one of Florida’s premier vacation destinations. The stunning, three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever witness. Aloha Kai is the ideal spot for a laid-back beach vacation, inviting you to lounge under shaded beach pavilions or relax by the largest pool on Siesta Key.

Villa 3 - Standard Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$466.04

You’ll love the light, bright coastal décor of the beautifully appointed and inviting Villa 31 at Aloha Kai. This little piece of paradise offers effortless living and a stay so enjoyable, leaving feels impossible. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach—the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key ranks among Florida’s top vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai provides the perfect setting for a laid-back beach vacation, inviting you to relax under shaded beach pavilions or unwind by the largest pool on Siesta Key.

Villa 31 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$453.83

Villa 2 at Aloha Kai is beautifully situated on Siesta Key, a popular barrier island along Florida’s West Coast. This family-friendly, gated resort community is nestled in the heart of Crescent Beach, which is ranked as the number one beach in the continental United States. Known for its dazzling white quartz sand and vibrant emerald-green waters, Siesta Key is among Florida’s top vacation destinations. The pristine, three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering the perfect setting for soul-soothing walks and unforgettable sunsets. Aloha Kai provides an ideal location for a relaxed beach getaway, inviting guests to unwind beneath shaded beach pavilions or by the largest pool on Siesta Key.

Villa 02 - Premium plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$561.23

Life is good at the beach! This light, bright, and beautifully maintained 2-bedroom, 1-bath villa at Aloha Kai is ready for your arrival—just drop your bags and head straight to the pool or beach. Featuring stainless steel appliances, an open-concept floor plan, and a screened porch, the villa offers the perfect blend of comfort and style. Located on Siesta Key, a renowned barrier island on Florida’s Gulf Coast, Aloha Kai is a gated, family-friendly resort nestled in the heart of Crescent Beach—the #1 rated beach in the continental United States. Known for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The pristine shores of Crescent Beach and the clear, calm waters of the Gulf of Mexico leave a lasting impression on even the most seasoned travelers. Stretching over three miles, Crescent Beach is perfect for soul-soothing strolls and witnessing some of the most breathtaking sunsets you’ll ever see. Aloha Kai provides the ideal setting for a relaxed beachside getaway, inviting you to lounge under shaded beach pavilions or cool off in the largest pool on Siesta Key—everything you need for a memorable vacation.

Villa 07 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

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Bath

Sleeps

Select Dates for Price

New photos coming soon! Villa 4 at Aloha Kai is the perfect beach getaway—light, bright, and designed to help you rest and relax. Spend your days lounging by the pool, soaking up the sun on the beach, or getting lost in a good book—the choice is yours. All you need is a willingness to unwind; everything else is provided for your comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its dazzling white quartz sand and emerald-green waters, Siesta Key is one of Florida’s top vacation destinations. The stunning three-mile stretch of Crescent Beach and the clear waters of the Gulf of Mexico captivate even the most seasoned travelers, offering soul-soothing walks and some of the most magnificent sunsets you’ll ever see. Aloha Kai is the ideal spot for a laid-back beach vacation, inviting you to relax under shaded beach pavilions or by the largest pool on Siesta Key.

Villa 4 - Premium - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

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Bath

Sleeps

Select Dates for Price