Holiday rentals with a pool in Osprey

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).

Secluded 3R Pool Home Retreat Near Sarasota

Welcome to The Osprey Oasis, a private retreat surrounded by lush tropical landscaping and just minutes from Sarasota’s beaches, parks, and downtown. This newly renovated 3-bedroom home features a bright open layout, a gourmet kitchen with stainless steel appliances, and spa-inspired bathrooms. Outside, relax in your own backyard paradise with a heated pool, screened lanai, lounge chairs, outdoor dining bar, grill, and fire pit for cozy evenings. Perfect for families, couples, or small groups, t

Saltwater Oasis

Welcome to your dream vacation home, where the tranquility of a private saltwater pool meets the convenience of a prime location, just minutes from Nokomis Beach, Legacy Trail and Siesta Key, the USA's #1 Beach. This home offers the perfect blend of comfort, style, and relaxation for your getaway. Our home even features a King sized master bedroom equipped with a sleeper sofa, ensuring young children can stay close to their parents. This is your haven for creating unforgettable memories.

Sunny Oasis/Beautiful House/Near Beach/Heated Pool

Beautiful House with 3 bedrooms, heated pool, mini golf and two-car garage. Great location. five-minute drive to the beach. near shopping plazas, restaurants, and the famous Legacy Trail perfect for biking, running, and more. Situated at a dead-end in a peaceful community. Lots of outdoor space around the house with beautiful palm trees and a large patio. bicycles, board games, cornhole, a gas grill, and more at your disposal. Lots of places to visit in the Sarasota and Venice area.

Heated&Renovated Pool•Beach Retreat•15m to Siesta

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.

"Starfish" at The Shore Beach Houses Resort

All new inside, this beautiful side by side duplex is separated for complete privacy with fences on the front and back patios. It's twin neighbor (The Jellyfish) can be rented also, and the doors opened up inside and outside to make this a 4-bedroom 2 bath home. Friends and larger groups can hang out together if they choose. Enjoy the heated saltwater pool, complimentary use of floaties, toys, beach chairs, coolers, & beach towels. Nokomis beach & restaurants within walking distance.

Windsor Lodge Unit #18, studio

Experience a luxurious Sarasota vacation rental at Windsor Lodge! Located directly on the golf course within the gated Oaks Golf and Country Club, this elegant retreat is ideal for couples and extended stays. Enjoy a bright, open-concept layout combining the living and sleeping area, plus a separate bathroom for privacy. Relax by the community pool or take in the golf views. You are just minutes from world-class Siesta Key beaches, premium shopping, and Sarasota’s finest dining!

Beautifully Remodeled Home with Pool Near Siesta

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

Tiki Oasis 3bed on .6 acre paradise 5 min to Beach

Relax with the whole family at this peaceful place to stay. Enjoy 2 master suites with 3 bedrooms and 3 bathrooms. A 5 min drive to Nokomis beach or downtown Venice, and walking distance to legacy trail, tennis courts, and playground in Nokomis park. Fast 500GB up/down internet speed around the property, Tiki bar nestled next to a heated pool and spa ( adtnl charge for spa). Fully stocked kitchen, beach-ready with cooler chairs umbrella wagon, and toys. 4 smart tvs

Creekside Paradise I

The 1970 sqft living space hosts 3 bedrooms, 2 bathrooms, an open living room with attached ‘library’, a dining area, as well as a fully equipped kitchen. From the caged pool area you have a view of the North Creek and our Boat Dock. The pool can be electrically heated and measures 32.80ft in length/13.12ft in width. You enter Creekside Paradise I thru the attached 2 car garage, where you can find the beach equipment (chairs, umbrella, cooler).

Vintage Villa 35 | Steps to Beach | Pool

Welcome to Vintage Villa 35. Just steps from the Gulf in Venice Island’s Golden Beach neighborhood. This bright, design-forward coastal retreat blends beachside ease with thoughtful details throughout. Walk to the sand, then spend your days exploring nearby Sharky’s, the pier, and historic downtown Venice, all just minutes away. Guests also enjoy access to a rare Olympic-sized community pool, a nostalgic nod to the property’s 1950s roots.

Florida Oasis Fully Equipped • 12 Min to Beaches

Spend time here and experience the vacation you’ve always imagined. This bright and spacious 2BR/2BA villa is just steps from the heated pool, hot tub, clubhouse, and tennis/pickleball courts. Enjoy both front and back outdoor sitting areas, a screened lanai, and access to a putting green, shuffleboard, library, and billiards. Minutes to Legacy Trail, Downtown Sarasota, Venice, and beautiful beaches including Siesta Key.