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Holiday rentals in South Sarasota

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Quick stats about holiday rentals in South Sarasota

  • Total holiday rentals

    Explore 390 holiday rentals in South Sarasota

  • Nightly prices starting at

    South Sarasota holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 12,880 verified reviews to help you choose

  • Family-friendly holiday rentals

    310 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 110 rentals that welcome pets

  • Holiday rentals with a pool

    270 properties feature pools

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wifi availability

    380 of South Sarasota holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across South Sarasota rentals

  • 4.8 Average rating

    South Sarasota stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in South Sarasota

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious living area features a comfortable light-colored sofa complemented by a vibrant blue accent chair. The floor showcases a bold black-and-white rug, while artwork adorns the walls. A side table with a lamp is visible, creating an inviting atmosphere for relaxation.
Home in South Sarasota
4.93 out of 5 average rating, 94 reviews

Ben's Bungalow | 8 min to Siesta Key | Gigabit Wifi

Ben's Bungalow is all about comfort and convenience. Just 3 miles and an 8 minute drive from Siesta Key Beach, it's the perfect home-base for your next Sarasota adventure and promises an unforgettable retreat for you and your crew. The large 3rd bedroom boasts an ultra-comfortable Nectar mattress and a 65” curved screen HDTV. Enjoy the Gigabit Wi-Fi, and the back-yard comes pre-stocked with fresh firewood, marshmallow sticks, and a privacy fence ready for you to make great memories with the fam.

Top guest favourite
Bungalow in Sarasota
5.0 out of 5 average rating, 11 reviews

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Experience life 4 blocks from the Gulf, ½ mile to Siesta Key — America’s #1 Beach. Effortless access to Siesta’s white sand beaches, Sarasota’s dining/arts scene, St. Armand’s & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds In Sarasota’s coveted ‘West of Trail’ Coastal District — marble chef kitchen, beach gear, Smart TVs, spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden & walk palm-lined lanes to cafés & glorious waterfront sunsets.

Guest favourite
A spacious living area is furnished with comfortable grey sofas and a central coffee table. A wall-mounted television displays scenic Florida imagery. Natural light filters through sheer curtains covering large windows, enhancing the overall bright atmosphere. The open layout connects to the dining area and kitchen.
Home in South Sarasota
4.82 out of 5 average rating, 73 reviews

Siesta Getaway-Minutes to Beach

Welcome to our Sarasota oasis! Fully renovated 3-bed 2-bath home embodies modern luxury, and just minutes from Siesta beach. Inside is spacious, stylish, open layout connecting living, dining, and kitchen. With 2 king and 2 queen beds, comfort is paramount. The sleek kitchen island/bar adds convenience. Unwind in a roomy bathroom with a large shower. Step outside to a vast backyard and patio, ideal for sunshine and bbq. This Sarasota gem guarantees an unforgettable escape - book your stay today!

Superhost
Bungalow in South Sarasota
5.0 out of 5 average rating, 4 reviews

New listing: Coastal Retreat 7-mins to Siesta Key

Bright mid-century modern 2BR/2BA retreat just 7 minutes from Siesta Key. Freshly upgraded with stylish coastal design, comfortable living spaces, and private outdoor space perfect for relaxing after beach days. Ideally located between the north and south bridges for easy access to Siesta Key Village, downtown Sarasota, Lido Beach, and St. Armands Circle. A perfect getaway for couples or snowbirds. No pets please. No parties or gatherings. No smoking of any kind. Yes to fun and relaxation

Guest favourite
A spacious sleeping area features a comfortable bed with white bedding, accompanied by a leather couch. A mounted television is positioned on the wall, and decorative plants add a touch of nature. A side table with a lamp complements the warm decor.
Guest house in South Sarasota
4.94 out of 5 average rating, 106 reviews

The Getaway

Relax in this comfortable and stylish space only 2 miles from Siesta Beach. The Getaway is the perfect spot to relax whether you're here on business or you've spent the whole day on the beach. The space is newly remodeled and you will lack nothing here! Enjoy the outdoor deck and two Nigerian Dwarf goats that live on the property. The Getaway is an apartment style space attached to the main home. It has it's own entrance and is completely private. The host lives in the main part of the home.

Top guest favourite
A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.
Home in South Sarasota
4.94 out of 5 average rating, 101 reviews

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

Guest favourite
A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.
Home in South Sarasota
4.98 out of 5 average rating, 149 reviews

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

Top guest favourite
A modern kitchen is presented with warm wooden cabinetry and stainless steel appliances. A large island provides seating with two white stools. Sunlight illuminates the space through a window above the sink, where a bouquet of flowers adds a vibrant touch.
Home in Sarasota
4.99 out of 5 average rating, 141 reviews

Siesta Breeze ~ Charming Coastal Cottage

Message me for 🔥🔥 last minute deals!! 5 miles from Siesta Beach, named No 1 Beach in the US, No 4 in the World by Tripadvisor; close enough to feel the sea breeze:) You will have 2 bathrooms, 2 bedrooms with queen beds and a flex room with a futon and work area, for 3 private sleeping areas. You will be located in the heart of Sarasota, with restaurants and grocers within a mile or two. The kitchen is fully equipped and the yard fully fenced. The host is conveniently located next door.

Guest favourite
An indoor pool is enclosed within a screened area, offering a clear view of tranquil blue water and surrounding trees. Comfortable outdoor seating is visible, complemented by a sunlit patio space. Large glass doors provide access to the pool area, enhancing the open feel.
Home in South Sarasota
4.97 out of 5 average rating, 219 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!

Guest favourite
The outdoor area features a well-maintained pool bordered by lush greenery. Several loungers and a shaded seating area invite relaxation. A vibrant red umbrella provides sun protection, while the sky above showcases a mix of clouds and blue, enhancing the serene atmosphere.
Home in South Sarasota
4.83 out of 5 average rating, 24 reviews

Siesta Shore House

Welcome to our newest Sarasota vacation rental! Sophisticated Pool house close to Siesta Key and downtown on a Cul de Sac. Get your pool house vacation and private Sanctuary! This house is designed to meet highest traveler's expectations. Every inch of the house has been touched to have the ultimate beach house experience. But all the details inside will not beat the brand new pool area that has been added to the house in 2023 and comes with all the modern features that make it stand out!

Top guest favourite
A modern kitchen features dark wood cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and dishwasher, are included. A doorway leads to a bright living area where natural light filters through a window, illuminating a cozy seating arrangement.
Home in Gulf Gate Estates
4.96 out of 5 average rating, 279 reviews

The Key Lime Cottage 2 miles from Siesta Key Beach

Great location. 2 miles from the # 1 rated Beach in America , Siesta Key . The cottage is near several other beaches as well. Walking distance to a Publix grocery store and 5 good restaurants. ⅕1 hour from Tampa and 2 hours from Orlando. The Key Lime Cottage is totally updated with new stainless steel & granite in the kitchen . There are two new beds ..... one is a queen size and the other is a full size. New tile and wood floors throughout. Quite neighborhood for walking .

Top guest favourite
A red lifeguard station is situated on the sandy beach, facing the ocean. The sky above features a mix of clouds and sunlight, creating a dynamic backdrop. Two individuals are seen walking along the shoreline, with gentle waves lapping at the sand.
Home in Sarasota
5.0 out of 5 average rating, 23 reviews

The Artist’s House - A Historic Florida Home

The Artist House is a lovingly restored historic property in an excellent location. A short 10 minute drive to the world famous Siesta Beach, very convenient to downtown Sarasota, shopping, and other amenities. Freshly renovated and decorated with original artwork and one-of-a-kind pieces of furniture. It has a new kitchen and new bathroom and it is located in a quiet historic neighborhood and has a lovely private yard. It is surrounded by large trees, lush vegetation.

Popular amenities for South Sarasota holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near South Sarasota's top sights

Siesta Beach

1,606 locals recommend

Siesta Key Beach

169 locals recommend

Detwiler's Farm Market

110 locals recommend

Siesta Key Watersports

45 locals recommend

Phillipi Estate Park

28 locals recommend

Tommy Knockers Gulf Gate

8 locals recommend

Other great holiday rentals in South Sarasota

Guest favourite
The exterior of a midcentury waterfront home is showcased, featuring a smooth driveway leading to a modern facade accented with orange and white. Lush greenery surrounds the property, including palm trees and manicured lawn areas, under a bright sky with scattered clouds.
Home in South Sarasota
4.94 out of 5 average rating, 90 reviews

Waterfront Home by Ralph Twitchell

Guest favourite
The front entrance is showcased with a vibrant blue door, set within a white stucco exterior. A pathway of colorful pavers leads to the entry. Lush green landscaping, including ornamental plants, is visible, contributing to the welcoming appearance of the home.
Home in Sarasota
4.95 out of 5 average rating, 43 reviews

Cozy! 3 Bedroom, 2 bathroom House

Guest favourite
Flat in South Sarasota
4.9 out of 5 average rating, 20 reviews

Only 10 minutes to Siesta Beach!

Guest favourite
A dining area is highlighted by a dark wood table surrounded by six chairs with blue patterned cushions. Light blue walls create a calm ambiance, complemented by a stylish chandelier. The open layout allows views into the adjacent kitchen and living space.
Home in South Sarasota
4.89 out of 5 average rating, 44 reviews

Tropical Oasis Near Siesta Key Beach, Air Purifier

Top guest favourite
Home in South Sarasota
5.0 out of 5 average rating, 68 reviews

Heated Pool + Spa + Mini Golf + Tiki near Siesta

Superhost
Home in South Sarasota
4.82 out of 5 average rating, 90 reviews

Beautiful 3bdr/2bth 2car garage with New Pool

Guest favourite
Home in Sarasota
5.0 out of 5 average rating, 7 reviews

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

Guest favourite
Home in Sarasota
4.86 out of 5 average rating, 88 reviews

Trish's Beach Retreat W/ Pool/Spa by Siesta Keys#2

When is the best time to visit South Sarasota?

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Avg. price£145£189£200£152£142£141£131£125£115£118£129£146
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°C

Frequently Asked Questions

  • What are the best places to stay in South Sarasota?

    Many visitors choose rentals near the beaches, arts districts, or family-friendly neighborhoods in South Sarasota. Stays often include access to outdoor amenities, walking paths, and community gathering spots.

  • What are the best things to do in South Sarasota with kids?

    Children often enjoy hands-on activities at local nature centers, splash parks, and interactive museums. Exploring sandy beaches, playgrounds, and wildlife habitats are also frequently suggested family outings.

  • What are some of the best things to do in South Sarasota?

    South Sarasota has outdoor recreation on beaches and in nature preserves, plus galleries, markets, and cultural performances. Explore walking trails, sample regional cuisine, or take part in local arts events.

  • How is the weather in South Sarasota?

    South Sarasota has mild winters from 51–72°F (10–22°C), warming to summer highs near 91°F (33°C) with increased humidity and rain. Lightweight clothing, sun protection, and umbrellas are frequently suggested for the changing conditions.

  • When is the best time to visit South Sarasota?

    Late winter and early spring are often recommended for milder temperatures and less rain, making outdoor activities more comfortable. Fall also brings seasonal events and pleasant beach days.

  • What are the best places to visit in South Sarasota?

    Explore parks, nature preserves, public art installations, and nearby beaches in South Sarasota. Local galleries, markets, and wildlife observation areas are commonly featured for visitors seeking a mix of culture and nature.

  • What are some hiking trails in South Sarasota?

    Explore shaded paths and water views on trails at nearby parks, nature preserves, or coastal conservation areas. Many routes are often recommended for birdwatching, walking, and connecting with local flora.

  • What are some family activities we can do in South Sarasota?

    Families can explore hands-on exhibits at museums, stroll nature preserves, or enjoy beach outings in South Sarasota. Community parks with playgrounds, splash pads, and picnic areas are frequently suggested for group fun.

  • What are some of the best day trip ideas from South Sarasota?

    Consider exploring nearby barrier islands, historic downtowns, or nature reserves for a change of pace from South Sarasota. Art venues, gardens, and wildlife tours are frequently suggested for day adventures.

  • Are there any pet friendly accommodations available in South Sarasota?

    South Sarasota has many pet-friendly accommodations, with neighborhoods near beaches, parks, and walking trails welcoming guests traveling with dogs or cats. Outdoor spaces and pet amenities are commonly included.

  • What are some local tips for visiting South Sarasota?

    Pack sunscreen, hats, and comfortable shoes to make the most of the sunny weather and outdoor options. Locals appreciate early morning beach walks, exploring farmers markets, and checking community event calendars for new experiences.

  • What is South Sarasota known for?

    South Sarasota is known for its Gulf Coast beaches, local arts scene, and nature preserves rich in wildlife. The area frequently draws people seeking outdoor recreation, cultural events, and relaxed community atmosphere.

  • What are the best hidden gems to explore in South Sarasota?

    Look for serene nature paths, small art galleries, and local farmer markets tucked into neighborhoods around South Sarasota. Quiet birdwatching spots and public murals are frequently regarded as lesser-known highlights.

  • What are the best foods to try in South Sarasota?

    South Sarasota has Gulf Coast classics such as fresh seafood, stone crab, and locally inspired dishes like grouper sandwiches. Key lime pie, citrus treats, and regional barbecue are frequently suggested by visitors and locals.

  • What should I bring for a trip to South Sarasota?

    Bring a hat, sunscreen, and lightweight clothing to prepare for sunny and warm weather. Comfortable walking shoes, a reusable water bottle, and swimwear are often recommended for outdoor activities.

  • What is the nightlife in South Sarasota like?

    Nightlife in South Sarasota combines casual waterfront venues, local restaurants, and live music spots. Evening markets and arts performances are often featured, creating a blend of laid-back and lively atmospheres.

  • What are the most popular events or festivals in South Sarasota?

    Cultural festivals and art fairs are often recommended throughout the year in South Sarasota, with music performances and markets highlighting local traditions. Seasonal celebrations around spring and early fall usually draw lively crowds.

  • Are there family friendly vacation rentals in South Sarasota?

    Family friendly vacation rentals are widely available in South Sarasota, featuring spacious layouts, kitchens, and easy access to parks or beaches. Many homes have amenities for children and group gatherings.

Destinations to explore