House vacation rentals in Siesta Key

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Top-rated house rentals in Siesta Key

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Guest favorite

Home in Sarasota

4.9 out of 5 average rating, 51 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!

Superhost

Home in Sarasota

4.78 out of 5 average rating, 54 reviews

Siesta Key Cottages Crescent 1D Beach/Pool/Hot Tub

4 separate two bedroom/two bathroom (+Sofa Bed) pool homes (Each sleeps 6) with only a 4 minute walk (no major streets to cross) to the #1 Beach in the USA: Siesta Key. First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Flat Screen TV’s: all bedrooms&living areas, Roku, fine linens, towels, Free bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. If you're a runner or walker you have miles of beach to take in!

Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 43 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.

Guest favorite

Home in Holmes Beach

5 out of 5 average rating, 61 reviews

Private Luxurious Ground Level Home

"A Turtle's Nest" Anna Maria Island Luxurious Ground Level Private Home with Heated Pool. This 3 bed 2 bath home is 1 blocks away from the world class private beach of Anna Maria Island. Our private, tranquil beach home is an open concept, light and airy, beautifully furnished retreat. 5-8 min walk to Shopping, Dining, Bars, Pickle ball, Tennis courts, Basketball courts, Skate park, Playground and more. ***Early luggage drop off available for a small fee. Message owner for more details.

Guest favorite

Home in Bradenton

4.97 out of 5 average rating, 38 reviews

The Sea Hut

Updated stylish townhouse. Great amenities include, resort style pool, basketball and tennis courts, playground, and sports field with picnic tables. Within 15-30 minutes from white powdery sand beaches including Siesta Key and Bradenton beach. Beach towels, chairs and beach/pool toys are provided for your enjoyment. Close to some of the best shopping locations including UTC mall and tons of amazing restaurants and bars. Theme/amusement parks are approximately 30 minutes to an hour drive.

Guest favorite

Home in Sarasota

4.92 out of 5 average rating, 283 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.

Guest favorite

Home in Sarasota

4.86 out of 5 average rating, 7 reviews

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.

Superhost

Home in Sarasota

4.71 out of 5 average rating, 132 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.

Guest favorite

Home in Sarasota

4.93 out of 5 average rating, 120 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.

Guest favorite

Home in Sarasota

4.99 out of 5 average rating, 357 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!

Guest favorite

Home in Siesta Key

4.96 out of 5 average rating, 100 reviews

Beachfront home with private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.

Superhost

Home in Holmes Beach

4.57 out of 5 average rating, 7 reviews

5 houses to beach, Pool, Hot Tub, Putting Green!

Maximize your outdoor experience in this 4 bedroom, 3.5 bath home located in the Heart of Holmes Beach! Not only does this house provide provide 4 balconies, a spacious pool area and covered patio, it's only a short block to the amazing gulf beaches Anna Maria is famous for. The house is well stocked and provides everything needed for a fun day at the beach or a day by the pool grilling a home cooked meal.