House rentals near Caspersen Beach

4.95 out of 5 average rating, 21 reviews

Cozy house near Siesta Key Beach

Relax with the whole family at this peaceful place to stay. Charming 3 bed/2bath house in a Gulf Gate Estates neighborhood, minutes away from white sands and turquoise water of Siesta Key Beaches (rated #1 beach in the nation), next to a beautiful lake park (2 min walking). Perfect to go on a morning run/bike ride or evening stroll to watch sunset Modern kitchen appliances. Fully fenced backyard with a large deck. Washer/Dryer. Garage. Plenty of restaurants and shopping nearby. Small pets are ok

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!

5 out of 5 average rating, 13 reviews

Home in Port Charlotte

Waterfront Escape on canal ocean access kayaks

This stylish waterfront home is perfect for group trips. This four bedroom two bath home has room for two families to fit comfortably. It has a variety of seating both indoor and outdoor to accommodate your stay. There is room to spend time together or find your own little quiet area. The home is located only minutes from the beach, pool, boat launch and fishing pier. Close to multiple waterfront restaurants and shopping. Only minutes from Sunseeker Resort, area boat tours and fishing charters

4.98 out of 5 average rating, 57 reviews

Dreamy Sunset Paradise by Downtown

This Absolutely amazing and Super Cozy Home located steps away from gorgeous Sarasota Bay with breathtaking sunsets! Prime location, close to Everything - Downtown, Beaches, Dining, Attractions, Shopping, & More! Our 2bd/2bath Retreat with gorgeous Open Living space, Cozy sitting areas, large TV, WiFi, fully equipped Kitchen, comfy King size beds, is all you need for an Extraordinary stay! Outside area w/private sitting space for Relaxation. 3 min drive to Downtown & 10 min to Lido Key Beach.

4.85 out of 5 average rating, 171 reviews

Beaches, Shopping, Sculling-Sarasota is calling!

Charming three bedroom two bathroom house. The HEATED SALTWATER pool is caged with a covered outside dining area along with an area to grill. Master bedroom comes with a private bath and a walk-in closet. Second bedroom comes with a queen bed and the third bedroom comes with 2 twin beds. Washer and dryer available on site. Five minutes to I 75. Minutes from the Sarasota airport. Minutes to the UTC and Benderson Park. Close to beaches and shopping. Can be rented short term or longer.

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, 20 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.

4.94 out of 5 average rating, 133 reviews

Hyde Park/Southside Village Modern 5 Star Home

BEST LOCATION/BEST VALUE ON 5 STAR HOME All 5 Star Reviews! Love This Location! Recently fully remodeled home. Three blocks to Southside Village, Morton's Market, fantastic shops and restaurants. Beautiful Arlington Park is down the street with pool, tennis, walking trails and dog park. 7 Minute Drive to Siesta Key or Downtown. **We love and welcome small dogs in our home. We need them declared at the time of booking. There is a small pet fee.

4.98 out of 5 average rating, 390 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, 61 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!