Holiday rentals with a pool in Osprey

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach

Step into your WINTER Holiday with a Beach Vacation! Now booking Spring! Reserve your March & April dates! Picture this: a rooftop deck, just a 5min walk to the pristine sand of Lido Beach, and surrounded by the charm St Armand's Circle with boutiques, and eateries, all within walking distance. Forget the conventional - this condo's got a secret. Tucked behind an unassuming door lies a vibrant space, drawing inspiration from speakeasy culture fused w/ a beach vibe. Your adventure starts now

4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres

Welcome to Oak Bahay Ranch, our beautiful 4+ acre ranch home with pool! Enjoy the tranquility of this 4 bedroom/2.5 bathrooms with a pool (heated during winter). Bike or drive the quick 2.5 miles to Nokomis and Casey Key Beaches! Oak Bahay Ranch is a nature lover's paradise, close to Legacy Trail, Sarasota County's premier 20+ mile biking/walking trail. Oak Bahay Ranch is an easy drive to world famous Siesta Key Beach (15 mins), downtown Sarasota (20 mins), and downtown Venice (10 mins).

3 bedroom Heated salt water pool close to Siesta

Your family will be close to everything when you stay at this centrally-located place. 15 minutes to Siesta Beach, 10 minutes to UTC mall, 15minutes to downtown, 20 minutes to SRQ airport. This home is fully remodeled, fully furnished, sleeps 8. We have 1 king size bed in the master, second bedroom is queen bed, 3rd bedroom is 1 full and 1 twin beds. This is open plan home with a big family room, 60" TV above electric fireplace, formal dining room seats 6 with the bar seats 4. Master has 55"TV

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Spectacular Sunsets! 15 min Siesta Key!

This villa is spacious and bright with lots of windows. The interior has just been updated. Tropical decor makes you feel like your’e at the beach. Huge flat screen TV. Tile flooring in the living areas and laminate in the bedrooms. Screened lanai overlooks palm tree and mature landscaping. Wireless fast speed internet included. It has everything you need for a short visit or extended stay. Fully equipped kitchen. Washer and Dryer. Beach chairs and towels. One car garage and driveway space.

Walk to beach. Pool view. Daily rentals V2

Villa 2 is overlooking the swimming pool Private entrance with self check in key pad entry King size bed Featuring 1 bedroom, 1 bathroom, large living room, Smart TV, A/C, fridge, freezer, toaster, free wifi Own parking space 2 minutes walk from your door to the beach access #13 Only 6 rentals in total Max 2 guest No smoking No pets Electronic Key Pad Entry No car needed Ground Floor, Good Value Great Location, walk to beach , shops, restaurants and bars. Bike rack available outside.

Your Modern Beachside Getaway!

Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!

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

Whisk your favorite person away to BayDreaming! Escape to this quiet 1BR/1.5BA Siesta Key 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!

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

Villa Maria: Minutes to Siesta Key!

2 BDRM/2 BTHRM condo very close to Siesta Key (3 min. drive or 20 min. walk). Totally UPDATED! Quality furnishings, super clean, ideal location. Have it all: Spacious condo in a peaceful setting. Just a few minutes drive over the south bridge to Siesta Key. Walking distance to great restaurants and shops on and off the key. Everything is within easy access by walking, car, bike, or free beach shuttle service. Come enjoy everything Sarasota has to offer.

Spacious 2 Bedroom Home | Near Beach | Heated Pool

This beautiful home just minutes from the beach offers 2 spacious king bedrooms, a queen sofa bed in the large open living area, and a full kitchen ready for entertaining. Gather your family around the dining room table for food and games and then relax on the lanai or have a float in the pool. The hosts provide Margaritaville frozen concoction machine, 2 bicycles, beach chairs, beach towels, shark tooth tools, and more.