Holiday rentals in Osprey

Lakefront Getaway in Sunny FL

Welcome to your lakeside retreat in sunny Florida! Our house offers stunning lake views and spacious, immaculate rooms. Just a short drive to Siesta Beach (#1 in the USA). The main house has 3 beautifully furnished bedrooms. The 4th bedroom in the separate guest house is included for groups of 10 guests; for smaller groups, it can be available for an extra fee. Relax by the large, clean pool in our private, gated property. Well-equipped kitchen, gazebo, grill, and family-friendly features await!

Minutes to Sand, Dog Friendly, Hot Tub Luxury

Watch the stars from your hot tub! Not camping, not glamping... This is luxury living for less! Private dog friendly property. Hooked up to city water, cold air in all rooms, immediate demand hot water and septic. This slice of paradise is minutes from the sand and has an elegantly appointed private master, two private loft bedrooms, sleeper sofa & 9' vaulted ceilings. Your private retreat includes the use of two kayaks, gazebo, beach chairs, 5G Wi-fi & Netflix, Prime, Paramount. Paradise!

Five Beach Retreat * Best Value @ Shorewalk Resort

Best Value in Shorewalk Resort * Near beaches of Anna Maria Island & IMG Academy Updated. Soothing sandy neutrals and crisp sea blues. Two bedrooms with full baths. Four beds. Two large sofas provide additional sleeping options. Fully stocked with beach gear. Access to the community's resort-style amenities, including 2 relaxing hot tubs, 2 heated pools, lighted tennis and pickleball courts, outdoor BBQ grills, basketball, shuffleboard & bocce ball courts, a billiard room, and a clubhouse.

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

Sunset Breeze Retreat

Welcome to your serene getaway in South Venice, FL! This cozy and spacious home is your perfect retreat, just minutes from breathtaking beaches and charming local shops and restaurants. Inside, unwind in comfort and style, with plenty of room to relax and enjoy quality time with loved ones. Embrace fun-filled evenings with a foosball table or savor the outdoors with a grill and beach supplies at your fingertips. Your dream vacation awaits in this inviting haven of relaxation and adventure.

Siesta Key Village & Beach w pool & pet friendly

Location and value. No fighting traffic for hours to get to Siesta Key. Park the car and relax. The heart of Siesta Key village waits just outside the back door, and everything is within walking distance at this centrally located condo with a heated pool. The #1 voted beach in the USA and its powder soft sugar sand is an 7-minute walk. Paradise and serenity have been found. One of the few places that will allow your small dog to stay. Also one of the few you can rent for less than a week.

Slowtide Cottage on Siesta Key

A high-end luxury cottage retreat on Siesta Key. No parties here -- the space was designed and outfitted for those who want a quiet place to relax. 2 bed 2 bath Cottage situated on the Intracoastal water of Siesta Key adjacent to the community pool, tiki bar, fishing dock, fishing pier and deeded private beach access. Meticulously remodeled former ww2 USAAF Barracks from the old SRQ Air Force Base. All new electrical, plumbing, lighting (Buster & Punch), Arhaus furniture.

Warm, Luxury Oasis in Central Sarasota

Choose to stay at a home which has it all. Professionally designed and hosted by a 10-year SuperHost, this property offers incredible value. Superbly comfortable beds and linens, SUPER FAST internet, thoughtful furnishings, tons of activities & games, fully equipped for babies and toddler needs, extremely central location, large, high-end TVs, a jacuzzi, 2-person hammock, in-ground fire pit…. And fur babies welcome… you name it, this home has it. Welcome to Sarasota Paradise.

The Cottage at Central Park II

If you are looking for the perfect family home to cater to your every need, then look no further! With plenty of space to spread out, natural light that pours into every room, an expansive and private fenced in yard, screened-in porch and outfitted kitchen- this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!