Semesterboenden med bubbelpool i Gulf Gate Estates

Sun-filled cottage with pool, walk to beach

Welcome to Palm Cottage. Our space is the perfect cozy getaway for any time of year. Recently renovated three bedrooms and one bathroom make this the perfect spot for two couples or a family. The private backyard includes a brand new pool with a hot tub and a sun shelf, as well as outdoor dining area and fire table. Enjoy a leisurely stroll to Siesta Key to play at the beach or grab a meal at one of the many restaurants. Home includes two bikes and all the gear you need for a day at the beach.

Quaint Cottage,150 steps away from Crescent Beach!

Nestled on the serene Crescent Street, this classic 1969 cottage, is just a short walk to the ground quartz sands of Siesta Key. The 500 sq foot private brick paver and stone backyard off the screened in lanai is fully fenced with custom built stainless outdoor kitchen, featuring a large grill, refrigerator, custom built stone bar with seating for 8 . Nearby is a blue glass gas fire pit with a seating area, over sized (9 ft. diameter) in ground "spool", loungers and a large circular daybed.

Heated Pools & Spa · Private Beach + Bay Views

Perfect for family and group beach stays, with reliable Wi-Fi and a dedicated workspace for flexible remote work. This oversized renovated 2‑bed, 2‑bath condo sleeps six: a king in the master and two queens in the second bedroom; both bathrooms serve the group for privacy and convenience. Enjoy full gulf-to-bay living with private beach access and supplied chairs, umbrella, cooler and wagon, plus two heated pools, a heated spa, gym, courts, bay views, free parking and keypad self check-in.

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Welcome to Siesta Fiesta, where dreams of relaxation become reality. With the backyard heated pool and hot tub, you have your own oasis to channel inner peace. If you’re feeling froggy, hop over to the beaches, take a kayak tour through the mangroves, a beautiful chartered sunset cruise, or try some of the local eateries that guests rave about! Whether you want to stay in, or go out, this home offers you everything you could need or want and will satisfy for pure relaxation or adventure!

Private house with loft

Have fun with the whole family at this brand new, modern private free standing guest house. Full bedroom with king size bed, with a finished loft including a queen bed. There’s also a queen pull out sofa in the living area. Enjoy your privately fenced backyard with a hot tub and putting green. Centrally located between Siesta Key beach and Nokomis beach. Hot tub is available upon request in off season months, April-October. There will be an additional $30 fee in off season months.

LJ's Cottage 2

STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

Zen Den: Bali Oasis near Siesta w/Pool & Hot Tub

Slip away to your own sanctuary just minutes from Siesta Key's legendary white-sand beaches. The Zen Den is a Balinese-inspired, 1-bedroom retreat wrapped in warm natural textures, soft lighting, and a seamless indoor-outdoor flow — designed for two people who want to completely unwind. Step through French doors to a the beautiful property grounds sparkling pool, bubbling hot tub, and a gazebo made for evening cocktails under the Florida sky.

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

Sunny Paradise w/Pool&HotTub 5 min to Siesta Key!

Family-Friendly 3BR Home w/ Private Heated Pool, Hot Tub & Backyard– Near Siesta Key! Located just minutes from world-famous beaches, and a wide variety of dining, shopping, and entertainment options, this home is the perfect base for your Sarasota vacation. Whether you’re planning a family trip, a couples’ retreat, or a friends’ getaway, you’ll love the blend of comfort, convenience, and fun!

Relax+ Jacuzzi | 9 Min to Siesta Key Beach

Important for privacy-conscious guests: You are renting a fully private home. There are no shared spaces of any kind. Stylish 4BR home 9 minutes from Siesta Key. Private jacuzzi, equipped kitchen, fast Wi-Fi, and outdoor grill. Sleeps 8, 2 bathrooms. Pet-friendly with fee. Please note: A separate structure on the property has its own entrance and does not share space with the guest home.

Last MIN AUG Sarasota #1 Luxury Villa! PRIV BEACH!

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!