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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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Superhost
Home in South Sarasota
4.83 out of 5 average rating, 23 reviews

Endless Summer | Private Pool & HOT TUB

​​​​​​​Welcome to your dream vacation home! Enjoy a fully fenced private backyard with heated pool and spa, ideal for relaxing or entertaining. Located just minutes from restaurants, shopping, and the pristine Siesta Key Beach! This 3-bedroom home is perfect for those who love coastal living without sacrificing proximity to urban amenities. Don't miss the chance to make this your new vacation haven! -Private Heated Pool - heated at NO extra cost from Nov 21st - Apr. 1st - Spa/Hot Tub - and More!

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, 98 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.

Top guest favourite
A covered patio space is surrounded by lush greenery and decorative plants. A light-colored table and two chairs are arranged on a tiled floor. Large, double doors in a vibrant blue lead to the outdoors, enhancing the welcoming atmosphere.
Guest suite in Sarasota
4.99 out of 5 average rating, 240 reviews

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Guest favourite
Home in South Sarasota
5 out of 5 average rating, 17 reviews

"Siesta on Lee" - NEW SRQ Home w/ Heated Pool!

Unwind in this charming Sarasota retreat! This 3 bed/2 bath home is just a 10-minute drive from both downtown SRQ and stunning Siesta Key, making it an ideal location. This property features 3 queen beds and 1 bunk bed, perfect for families or groups. With 2 full bathrooms, a fully equipped kitchen, cozy living room, game room, and private pool (option to HEAT) with loungers, the home comfortably hosts up to 8 guests. You've found the perfect place to call home while you're away from yours!

Top 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, 144 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
Home in Sarasota
5 out of 5 average rating, 22 reviews

4BRHeated Pool•Fire Pit•Pool Table Mins Siesta Key

Welcome to Casa Trinidad — Your Coastal Oasis in Sarasota! Escape to Casa Trinidad, a bright and stylish 4-bedroom coastal retreat located just minutes from world-famous Siesta Key Beach and vibrant Downtown Sarasota. Whether you’re planning a family getaway, a couples’ trip, or a relaxing retreat with friends, this home offers everything you need for the perfect Florida stay — a heated private pool, fire pit, BBQ area, game room, and all the cozy coastal touches that make it unforgettable.

Guest favourite
Home in Sarasota
5 out of 5 average rating, 8 reviews

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

Superhost
Home in Siesta Key
5 out of 5 average rating, 3 reviews

The Siesta Key Retreat - An Island Garden Oasis!

Your family will be close to everything when you stay at this centrally-located place on Siesta Key while still enjoying the private garden oasis this home has to offer. Just steps from the quaint shell beach or a bike ride to the beautiful sand of Siesta Key beach to spend the day or venture to the cool vibes of Siesta Key Village for dinner and shopping!. Additionally, you're only a few miles from the vibrant downtown Sarasota and St. Armand's Circle (26-VR-000095)

Guest favourite
Home in South Sarasota
4.9 out of 5 average rating, 10 reviews

Luxe Modern Home - Private, Friendly & Stylish

Welcome to Lux Modern Home, a stylish modern home just minutes from the world-famous Siesta Key Beach. Thoughtfully designed with clean lines, coastal tones, and smart features, this 1,400 sq ft retreat offers the perfect balance of comfort, privacy, and contemporary living. Whether you’re here for beach days, sunset walks, or a relaxing getaway, this home is an ideal base for couples, families, or friends seeking a calm and upscale coastal experience.

Guest favourite
Home in South Sarasota
4.89 out of 5 average rating, 9 reviews

Sand & Sea Retreat, Private Heated Pool.

Welcome to Sun & Stone Retreat — a spacious 5-bedroom Sarasota escape designed for comfort, connection, and easy coastal living. Enjoy your private heated pool, open living spaces, and room for everyone to relax. Perfect for families or groups, this home is just 10 minutes from beautiful beaches, dining, and local attractions. Whether you’re gathering poolside or heading out for beach days, Sun & Stone Retreat is your ideal Florida getaway.

Top guest favourite
A stylish living area features a round wooden table surrounded by two light-toned chairs. The space is complemented by a modern kitchen with bar seating and pendant lighting. Light-colored walls and soft lighting contribute to a calm atmosphere, with a piece of wall art adding a decorative touch.
Home in South Sarasota
4.95 out of 5 average rating, 39 reviews

Experience "Old Florida" at the Coral Cottage

BRAND NEW REMODEL AND BETTER THAN EVER! Designer furnished, cozy, stylish Vintage Florida home on Phillippi Creek. Fishing rods, kayak and paddle board included. See an abundance of wildlife, including birds and manatees right at your waterfront deck! One bridge to the Bay. Dock space available! Eclectic, quiet neighborhood on the unbeaten path yet so close to beaches (3 miles!) shopping, restaurants and more!

Top guest favourite
Home in Arlington Park
4.95 out of 5 average rating, 41 reviews

Modern Home Heated Pool near Siesta & Downtown

Escape to our brand-new, modern Sarasota home, perfect for families! Enjoy a private heated saltwater pool just steps from the master suite. Located minutes from the world-famous Siesta Key Beach and vibrant downtown Sarasota. This stylish oasis comfortably accommodates up to 10 guests, offering the ultimate Florida retreat with all-new furnishings and a fully equipped kitchen. Your private getaway awaits!

Popular amenities for South Sarasota holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in South Sarasota

Top guest favourite
A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.
Home in Sarasota
5 out of 5 average rating, 36 reviews

The Palms Away

Top guest favourite
Guest suite in Sarasota
5 out of 5 average rating, 20 reviews

siesta breeze paradise suite

Top guest favourite
A screened-in outdoor seating area is featured, furnished with a large sectional sofa adorned with red accent pillows. A low coffee table holds a bowl of fresh fruit and drinks, overlooking a sparkling pool surrounded by lush greenery.
Home in Sarasota
4.98 out of 5 average rating, 99 reviews

Modern Pool House Sealand 3/2 near Siesta

Guest favourite
A private backyard features a heated in-ground pool surrounded by spacious pavers. Lounge chairs are positioned along one side, with a shaded table and umbrella nearby. Lush greenery lines the perimeter, providing a natural backdrop for relaxation and leisure.
Home in South Sarasota
4.91 out of 5 average rating, 23 reviews

The Pink Pineapple - Your Cozy Sarasota Home

Superhost
Bungalow
5 out of 5 average rating, 4 reviews

New listing: Coastal Retreat 7-mins to Siesta Key

Top guest favourite
Apartment in Sarasota
4.97 out of 5 average rating, 62 reviews

Charming Poolhouse · 1BR · Close to Siesta

Top guest favourite
Guest suite in Sarasota
5 out of 5 average rating, 79 reviews

siesta breeze suite

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
4.85 out of 5 average rating, 20 reviews

Siesta Shore House

When is the best time to visit South Sarasota?

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Avg. price£147£191£202£159£126£132£132£126£117£119£130£148
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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