House holiday rentals in Osprey

4.89 out of 5 average rating, 56 reviews

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!

4.93 out of 5 average rating, 110 reviews

Sunny Sarasota Vacation Home - VR2400236

Quiet Neighborhood - Single Private Home, Great Location! This beautiful home includes 3 bedrooms, 2 bathrooms and sleeps up to 10 people. Near #1 Rated SIESTA KEY BEACH & LIDO KEY BEACH. Come and relax in this newly renovated home. Large living room, dining room and lanai to accommodate your friends & family. 5 TV's, DVD players, Cable, Internet. Fully equipped kitchen & laundry. Bus stops, grocery stores & restaurants are near by. Base rate covers 6 guests; $20.00/night/additional guest.

4.96 out of 5 average rating, 122 reviews

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

4.92 out of 5 average rating, 294 reviews

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

Our bright and contemporary Heart Villa offers the quintessential Sarasota downtown and beach experience. It is nestled among tropical trees in a charming cul-de-sac in historic Laurel Park – right in the heart of downtown with loads of restaurants, boutiques, and sights on offer. Several fantastic beaches are just 5-mins ride away! And the villa's private garden is the perfect place to enjoy alfresco dining! We’ve poured our hearts & souls into this villa, it's our family business.

4.95 out of 5 average rating, 19 reviews

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.

Superhost

4.71 out of 5 average rating, 135 reviews

Private house, 3 bed, 2 bath with back yard. WIFI

Welcome to your home away from home in charming Sarasota! Experience the vibrant core entertainment, exquisite dining, and enchanting opera house near downtown. Immerse yourself in renowned arts and live performances. Just 3 miles away, cross the iconic Ringling Bridge to St. Armand's Circle and pristine beaches. Siesta Beach is a mere 5 miles away for sun and sand. With a central location and inviting atmosphere, this is the perfect place to explore Sarasota's offerings.

4.87 out of 5 average rating, 126 reviews

Home in Punta Gorda

Coastal cottage in Heart of Downtown

Quaint and airy historical cottage in the heart of downtown! THE BEST LOCATION...half a block to restaurants, just blocks from Harbor walk, less than a mile from Fisherman's Village. My home is tastefully decorated and gives you the feel of old Florida with all the conveniences. You can relax on the front porch swing or sip a cocktail and people watch! There is so much to do within walking distance of the house. And Punta Gorda always has something going on

4.9 out of 5 average rating, 10 reviews

Home in Bradenton

Modern Resort-Style Townhouse

Experience Luxury Living in a Brand New Townhouse! Be the first to enjoy this stunning newly constructed 3 bedroom townhouse. This stylish home boasts 2000 Square feet of modern, elegant space across two floors. Features - Spacious bedrooms - Ample living space - Exclusive community Amenities - Full-service clubhouse - Dining and Bar - Relaxing resort-style pools Basic internet, cable, and lawn maintenance included. Book now for a five-star experience!

4.98 out of 5 average rating, 388 reviews

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!

4.93 out of 5 average rating, 60 reviews

Home in Bradenton

Pickleball! Pond! Private Heated Pool! Foosball

Welcome to Once Upon A Pond, by Stayawhilewithus! If travel is on the horizon, set your sails to luxury and tranquility at this newly updated 4BR/3BA getaway. The heated private pool offers gorgeous vistas of the pond in the backyard, so take your relaxation to another level with the scenic views and some mesmerizing bird watching. And don't forget to enjoy the pickleball court in our side yard - it'll be great fun for the whole family!

5 out of 5 average rating, 11 reviews

Home in Punta Gorda

Stunning! Luxury waterfront home

STUNNING!! LUXURY WATERFRONT HOME - HEATED POOL- Close to Harbor/Fish Village -PREMIER HOST reviews averaging 5.0 since 2018 on other site. -Modern, newly updated home with open layout allowing for enjoyment of the cool waterfront breezes. -Boat dock with very close Harbor access within 10 minutes. -Southern exposure, full sun, heated pool, and waterfront. Oversized pool extends along large portion of rear of home.