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Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

*Recently Updated* Cozy Oasis, centrally located

This cozy yet spacious apartment is very centrally located... Just 5 min from downtown, 10-15 min from Siesta and Lido bch and St Armands Crl, and within walking distance of the historic Amish district. The newly completed Legacy Trail (perfect for walking, biking...) is less than a 5-minute walk away. The space is very private and clean and Ive taken extra measures to ensure your absolute peace and comfort. It includes all the amenities you'll need to make your getaway a memorable one.

APRIL is OPEN ! 1 min to beach, CUTE, Pets OK!

Our unique villas sit just 1/2 mile from one of Florida’s most pristine beaches. Many local restaurants and shops are easily accessible. The villas also have an attached yard/field perfect for pets, 40 lb max total weight . The local beach is considered one of Florida’s finest with only one access point for over 7 miles of private beach! We have been super hosts for years and love creating great memories Please read our reviews! Two adults, two kids maximum capacity...:) Chris and Michelle!

Sand Dollar Retreat

Escape to our relaxing 2-bedroom home in Osprey, Florida, just minutes from the stunning beaches of the Gulf of Mexico, pristine golf courses and MLB spring training. This peaceful retreat sleeps up to 7 adults and offers a perfect blend of comfort & convenience. The master bedroom features a queen bed and the second bedroom has a bunkbed sleep system with a queen mattress on bottom and twin mattress elevated above. There is also an office with a daybed & trundle for additional sleeping space.

Quiet Gulf & Canal View 1 BR -2 Supyaks-Htd Pool

Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA condo - just an 8-minute walk to Turtle Beach! Perfect for couples, it features a private deck with canal and Gulf views , a heated pool for sunset swims, 2 supyaks and a plush king bed for cozy nights in. Enjoy garage parking, beach gear, and a peaceful, welcoming community. Whether you're here to relax or reconnect, this coastal retreat offers the perfect mix of romance or just plain serenity on sunny Siesta Key!

Lovely 2-Bedroom Condo, 7 min from Siesta Beach

Welcome to our beautiful condo, which is located just 4 miles to Siesta Key! Enjoy Vamo Park, just steps from our door, where you can launch a kayak or paddle board. Fishing is also allowed from this location. There are also picnic tables at the park where you can enjoy sunset. Our condo is fully equipped with all the necessary things you need. Beach chairs, shops, theaters, gyms, and the legacy trail, Sarasota Sharks Inc. Plus more. These are just a few of the things available in the area.

Bright & Modern Getaway - Walk to Beach and Dining

Welcome to your clean, modern beach retreat just 2 blocks from the Gulf. This fully renovated 3BR/2BA home is perfect for families and groups with all new furnishings, mattresses, linens, and appliances. Featuring a private king suite with wet bar & separate entrance, 2 queen bedrooms, and a fully stocked kitchen. Walk to Nokomis beach, waterfront dining, ice cream and local shops. Fast WiFi, smart TVs, coffee bar, washer/dryer, and all beach gear provided for a stress-free coastal escape.

Chic & Cozy Getaway • Near Siesta Key Beach

Renovated modern studio in a duplex home with private entrance, full kitchen, bathroom, laundry, and parking. Nestled in a quiet, safe neighborhood just minutes from Lido, Turtle, Nokomis beaches, and Siesta Key—#1 beach in America with soft, white sand. Walk to restaurants, Starbucks, Total Wine, Costco, Target, CVS, Bay Village Assisted Living, Selby Aquatic Center & Vamo Bay Park. Short drive to downtown Sarasota, Venice & scenic bike trails. Ideal for beach getaways or extended stays!

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.

Modern 1BR Near Siesta Key + Private Parking

Private coastal retreat minutes from Siesta Key Beach. This spacious 950 sq ft upstairs apartment features soaring ceilings, a bright open layout, and a private entrance. Enjoy a king-sized bed, full kitchen, in-unit washer and dryer, fast Wi-Fi, and dedicated parking. Perfect for couples or guests seeking a peaceful, comfortable stay near the beach. Consistently rated 5⭐ for cleanliness, comfort, and communication. Ideal for couples seeking a peaceful, comfortable beach stay.

Short walk to beach 4, King bed, Dog Friendly

Location Location Location! Experience island life from this 1 BR, 2nd floor condo walking distance to everything. A few steps to Venice beach, and a short walk or bike ride down the tree lined boulevard takes you to Historic Downtown Venice where you'll find, Restaurants, Cafes, and Boutiques. Pack your bathing suit, and flip flops, with all the comforts of home, and all beach gear provided, that's all you'll need here! Sofa bed also available.

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!