Holiday rentals in South Sarasota
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Top-rated holiday rentals in South Sarasota
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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. With effortless access to Sarasota’s dining & arts scene, Siesta’s white sand beaches, St. Armand’s, & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds Situated in the coveted Coastal District (‘West of Trail’) — chef kitchen, beach gear, Smart TVs, marble spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden, & walk palm lanes to cafes, and waterfront sunsets.
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.
Waterfront Siesta Key / Kayak to the Bay & Beaches
North end of Siesta Key. Entire place entry level . Waterfront king suite on Bayou Louise with private entrance & direct water access. One large parking spaces out front. An old town Malibu tandem Kayak is complementary for our guests ride to Sarasota Bay in minutes and reach Lido key, Bird Key, and Roberts Bay . Just 2 miles to North village, 2.6 miles to Siesta Beach. Freshly Remodeled ! Self check in keyless . remote work escapes, great relaxing for couple get away in the best of Sarasota!
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.
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!
Tropical Oasis Heated Pool Hot Tub Near Siesta Key
Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!
Spacious Sarasota family home Mins from the beach
Experience the ultimate Sarasota family getaway in our luxurious and spacious 4 bedroom, 2 bath home, just 5 miles from Siesta Key beach. Comfortably sleeps 9, pets are welcomed too. Newly-renovated and filled with modern amenities, enjoy the convenience of a fully equipped kitchen and a cozy outdoor backyard. Local fine dining options, shops and supermarkets are less than a mile away or relax at home with our charcoal BBQ grill and fire pit. Book now for a memorable beach getaway!
Heated Pool + Spa + Mini Golf + Tiki near Siesta
🌴 Heated Pool • Spa • Tiki Hut • 10 Min to Siesta Key Private pool oasis just minutes from Siesta Key — designed for relaxing days and unforgettable nights. Enjoy a heated pool (heated at NO extra cost from Nov 21st - Apr. 1st), spa with waterfall, tiki hut lounge, and a fully screened lanai for indoor-outdoor living. Relax poolside, play outdoor games, and unwind under ambient evening lighting. Perfect for families, couples, and groups seeking a memorable Florida getaway.
The Sand Castle - Backyard Oasis Mins from Siesta!
*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want!
Downtown Sarasota | Casa de Zara
Welcome to Casa de Zara! Immerse yourself in Sarasota history by staying in our quaint Adobe style home built in 1925 with a serene garden filled with plants and trees native to Florida. You will be 1 mile from Main St. and 4 miles to Lido Key. One block over you will find a fun filled park with tennis and pickle ball courts, a walking path and basketball courts. Less than a mile away is Bayfront Park which is perfect for watching sunsets!
Adorable studio close to Siesta beach!
Come stay in this private studio with its own fenced in patio in the back! Has shared washer and dryer. New Queen bed ,pullout couch (twin). gas grill,toaster oven/airfryer, microwave , hot plate for cooking and full fridge plus ac unit. Rainfall showerhead and river stones on shower floor. beach chairs ,towels available. Off street parking in driveway. The famous, huge fresh market " Detweilers" is only 1.5 miles away
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!
Popular amenities for South Sarasota holiday rentals
Stay near South Sarasota's top sights
Other great holiday rentals in South Sarasota
Sarasota's Luxury Oasis
The Palms Away
Luxury Pet friendly home, 2.7miles to Siesta Key!
Stunning New 3 bed 3 bath pool home by Siesta Key!
Private Getaway Near Siesta Key!
Private Heated Pool Retreat for Two Families
The Siesta Key Pool House – Private Inland Oasis
Siesta Getaway- 3.5 miles to beach 3/2 pool home.
When is the best time to visit South Sarasota?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £133 | £185 | £201 | £158 | £125 | £131 | £131 | £125 | £116 | £118 | £129 | £147 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 18°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.
Quick stats about holiday rentals in South Sarasota
Total holiday rentals
Explore 380 holiday rentals in South Sarasota
Nightly prices starting at
South Sarasota holiday rentals start at £30 per night before taxes and fees
Verified guest reviews
Over 11,980 verified reviews to help you choose
Family-friendly holiday rentals
300 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 100 rentals that welcome pets
Holiday rentals with a pool
270 properties feature pools
Rentals with dedicated workspaces
240 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!
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- Family-friendly rentals South Sarasota
- Rentals with a patio South Sarasota
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- Rentals with outdoor seating South Sarasota
- Pet-friendly rentals South Sarasota
- Rentals with pools South Sarasota
- Waterfront rentals South Sarasota
- Fitness-friendly rentals South Sarasota
- House rentals South Sarasota
- Rentals with beach access South Sarasota
- Rentals with a hot tub South Sarasota
- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- John's Pass
- Bean Point Beach
- Coquina Beach
- Anna Maria Island Beach
- Turtle Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Caspersen Beach
- Cortez Beach
- Tampa Convention Center
- St Pete Beach
- Hard Rock Casino
- Jannus Live
- Anna Maria Public Beach
- Manasota Key Beach
- River Strand Golf and Country Club
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- Englewood Beach