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House holiday rentals in Siesta Beach

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Top-rated house rentals in Siesta Beach

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Home in Longboat Key

4.86 out of 5 average rating, 110 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 114 reviews

Power On! Fenced Yard-3.5 miles to Siesta Key

Escape to this beach inspired bungalow with a fully equipped kitchen and a fenced yard to relax in the sunny outdoors. Only 10 minutes to Siesta Key Beach! Enjoy the Sarasota beaches, museums, parks and downtown Sarasota, all just minutes away. Centrally located to grocery stores and restaurants. From coastal decor to comfortable beds, every part of your experience was thoughtfully curated by the owners to allow you to sit back, so feel free to put your feet up and relax at Barefoot Bungalow,

Guest favourite

Home in Bradenton

4.91 out of 5 average rating, 164 reviews

Htd Saltwater Pool- Near Beaches - 6bd/3ba

Relax in this stunning mid-century modern house near the beach with NEW saltwater pool with stone deck & splash pad/sun deck! Make your own childhood dreams come true for the kids with a backyard treehouse that is sure to make lifelong memories! This palm oasis is sure to please everyone! We have thought of everything, including all the vacation essentials for home, pool, & beach! Don't miss your chance to relax on America's favorite beaches at Anna Maria Island & Siesta Key- just minutes away!

Guest favourite

Home in Sarasota

4.92 out of 5 average rating, 227 reviews

*Downtown home 10min. drive to beach; walk DT*

In the heart of Gillespie Park, this bright & spacious home is a 10 min. drive to Lido Beaches and within walking distance to downtown shops, grocery, farmer's market, opera house, restaurants, bars, live music, tennis, parks, antique shops and performing arts centers. Old Florida bungalow on the outside, inside it's a recent, modern remodel with new appliances, kitchen, bathrooms, flooring and fixtures. A banyan tree offers private, shady repose on the back deck w/ grill and dining area.

Guest favourite

Home in Sarasota

4.86 out of 5 average rating, 162 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.

Guest favourite

Home in Sarasota

4.92 out of 5 average rating, 284 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.

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 favourite

Home in Bradenton Beach

4.82 out of 5 average rating, 133 reviews

50 Steps to Beach Villa Hot Tub 1bd modern cottage

Luxury Beach Cottage w/ HOT TUB, Fire Pit & BBQ. 1 bed/2bath sleeps 4 This is your chance to enjoy a unique getaway on the nicest beach! Stay in our newly remodeled beach cottage. White sandy beach & turquoise water is literally 50 ft from the door. Everything you need for a delightful & relaxing day at the beach is included. Chairs, beach towels, umbrella, snorkels, masks & a cooler. Enjoy the convenience of this premium location across Gulf blvd to Beach.

Guest favourite

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 favourite

Home in Sarasota

4.99 out of 5 average rating, 358 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 favourite

Home in Venice

4.93 out of 5 average rating, 115 reviews

In Great shape after Milton -Gorgeous Pool! - os

Beautifully decorated 3 bedrooms, 2 bathrooms, attractive family room & open concept kitchen with breakfast room overlooking private pool. On desirable Island of Venice, “Villa Sorrento” is only 8 minute walk to beach. Just under a mile stroll or quick drive to Historic Venice Avenue's unique shops, restaurants. Low-key quiet respectful vacationers only. 2 car max. no visitor parking. No pets. No smoking inside or out

Guest favourite

Home in Siesta Key

4.96 out of 5 average rating, 101 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.

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Popular amenities for Siesta Beach house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Bradenton

4.76 out of 5 average rating, 227 reviews

Tropical Paradise - Private Pool - Close Beaches

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 120 reviews

Lake Front House with a Pool

Home in North Port

4.81 out of 5 average rating, 130 reviews

Luxury villa 4 bdr with a heated pool (14guests)

Home in North Port

4.8 out of 5 average rating, 102 reviews

Well Appointed and relaxing Pool Home

Guest favourite

Home in Bradenton

4.89 out of 5 average rating, 216 reviews

Beautiful pool home minutes from Anna Maria Island

Home in Bradenton

4.86 out of 5 average rating, 280 reviews

Large 4 bedroom pool home tiki bar close to Ami

Guest favourite

Home in Anna Maria

4.93 out of 5 average rating, 103 reviews

Charming house w/heated pool,steps to beach-Unit A

Home in Bradenton

4.88 out of 5 average rating, 122 reviews

Coastal Charm

Weekly house rentals

Guest favourite

Home in Bradenton

4.81 out of 5 average rating, 141 reviews

Hot tub/Pool! Pet friendly (for fee) Fenced yard

Guest favourite

Home in Bradenton

4.96 out of 5 average rating, 211 reviews

Cozy Cottage R-Steps to Riverwalk/Close to Beaches

Home in Sarasota

4.83 out of 5 average rating, 116 reviews

Seagrass Cottage- Hot tub near downtown/beaches

Home in Bradenton

4.84 out of 5 average rating, 244 reviews

Comfortable & modern house in Central Bradenton

Guest favourite

Home in Anna Maria

4.99 out of 5 average rating, 102 reviews

1 block to Beach on Pine Ave! Private Heated Pool

Home in Sarasota

4.94 out of 5 average rating, 139 reviews

White Sands Villa - Heated Pool/Spa - Near Beaches

Guest favourite

Home in Sarasota

4.94 out of 5 average rating, 150 reviews

Wood Street Retreat 4/2 Near Beaches & Downtown

Home in Holmes Beach

4.87 out of 5 average rating, 103 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Private house rentals

Home in Bradenton

4.97 out of 5 average rating, 34 reviews

Amazing heated pool and grill! The Farm House

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 56 reviews

2223 Doud Street, Sarasota, FL

Guest favourite

Home in Sarasota

4.97 out of 5 average rating, 221 reviews

Your private retreat near Siesta Key Beach.

Home in Venice

4.9 out of 5 average rating, 52 reviews

The Ripple Inn At Fennario

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 92 reviews

Beautiful heated pool home, minutes from beaches

Guest favourite

Home in Sarasota

4.88 out of 5 average rating, 33 reviews

Sea la Vie - heated pool, 4b2b, stocked kitchen

Guest favourite

Home in Siesta Key

4.82 out of 5 average rating, 90 reviews

Tiki-Bar, Balcony, Patio, 250 steps Beach/Village!

Guest favourite

Home in Englewood

5 out of 5 average rating, 32 reviews

Manasota key house with private boat dock

Destinations to explore