South Sarasota holiday lettings

We found 6,948 holiday rentals — enter your dates for availability
Discover a selection of 36 homes and other holiday rentals in South Sarasota that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – South Sarasota

Showing deals for:1 Jan - 8 Jan

Private kitchen
Pool
Interior
Living area
Exceptional
(28 reviews)

Rare private beachfront estate on the Gulf.

Nokomis

8% off
£27,896
for 7 nights, 1 home
£3,985 per night
includes taxes & fees
Rare private beachfront estate on the Gulf.
Living area
Living area
Outdoor dining
Pool
Exceptional
(81 reviews)

Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate

Sarasota

7% off
£2,251
for 7 nights, 1 cottage
£322 per night
includes taxes & fees
Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate
kitchen window overlooking private backyard
Kitchen area with open concept…to right is door to car port/screened porch
2 bikes (w/ bike lock) avail for your use, enjoy a cruise in the neighborhood
55 inch smart TV.  Bring your Netflix login!
Exceptional
(31 reviews)

Chic cottage, Vamo area, close to beaches, pet friendly, kayaks, large backyard

Sarasota

5% off
£1,387
for 7 nights, 1 cottage
£198 per night
includes taxes & fees
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks, large backyard
Interior
Interior
Room
Private kitchen
Exceptional
(21 reviews)

Bayshore Gardens remodel with hot tub + fire pit + walk to park.

Bradenton

7% off
£1,986
for 7 nights, 1 home
£284 per night
includes taxes & fees
Bayshore Gardens remodel with hot tub + fire pit + walk to park.
Living area
Living area
Exterior detail
Private kitchen
Very good
(8 reviews)

Sarasota Modern Home minutes to Siesta & Downtown

Sarasota

5% off
£1,774
for 7 nights, 1 home
£253 per night
includes taxes & fees
Sarasota Modern Home minutes to Siesta & Downtown
Exterior detail
Living area
Interior
Outdoor dining
Exceptional
(6 reviews)

New modern home with salt water heated pool located minutes from SiestaKey Beach

Sarasota

8% off
£10,251
for 7 nights, 1 home
£1,464 per night
includes taxes & fees
New modern home with salt water heated pool located minutes from SiestaKey Beach
Marina
Outdoor dining
Fitness facility
Waterfront restaurant on premisis with live music
Very good
(164 reviews)

SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail

Sarasota

8% off
£625
for 7 nights, 1 room
£89 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Living area
Private kitchen
Interior
Living area
Exceptional
(69 reviews)

Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches

Bradenton

7% off
£2,719
for 7 nights, 1 home
£388 per night
includes taxes & fees
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Outdoor dining
Pool
Fitness facility
Room
Excellent
(156 reviews)

Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL

Sarasota

8% off
£633
for 7 nights, 1 room
£90 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Pool
Pool
Pool
Pool
Exceptional
(93 reviews)

Oceanfront home

Sarasota

8% off
£4,667
for 7 nights, 1 home
£667 per night
includes taxes & fees
Oceanfront home
Large dining room opens to living area, offering seamless entertaining space.
Sophisticated and serene Mediterranean beach home.
75" TV perfect for movie nights.
Private, heated pool and spa with canal views and your own private dock.
Exceptional
(14 reviews)

Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

Siesta Key

7% off
£6,064
for 7 nights, 1 home
£866 per night
includes taxes & fees
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock
Living area
Private kitchen
Terrace/patio
Exterior
Exceptional
(7 reviews)

A cozy, perfectly located house!

Sarasota

7% off
£1,601
for 7 nights, 1 home
£229 per night
includes taxes & fees
A cozy, perfectly located house!
Dining
Beach
Exterior
Private kitchen
Exceptional
(53 reviews)

Siesta Key Beach Cottage

Siesta Key

7% off
£1,879
for 7 nights, 1 cottage
£268 per night
includes taxes & fees
Siesta Key Beach Cottage
Room
Private kitchen
Interior
Living area
Exceptional
(5 reviews)

Central City Condominiums #203 2BR/2BA

Sarasota

7% off
£1,111
for 7 nights, 1 apartment
£159 per night
includes taxes & fees
Central City Condominiums #203 2BR/2BA
Front (living) room
additional bar area seating
Outdoor fire pit. Please note guests are responsible for refilling propane
sliding door in kitchen leads to patio area
Exceptional
(129 reviews)

HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes

Sarasota

5% off
£2,603
for 7 nights, 1 home
£372 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Living room with connected enclosed patio
Siesta Key Beaches are ranked in the global top-10
Plenty of room to host an evening in
Main bedroom with direct access to enclosed balcony
Exceptional
(14 reviews)

Sundeck with Ocean View, Private Access to Beach & 500ft to the Village

Siesta Key

8% off
£4,426
for 7 nights, 1 apartment
£632 per night
includes taxes & fees
Sundeck with Ocean View, Private Access to Beach & 500ft to the Village
View from room
Pool
Fitness facility
Outdoor dining
Excellent
(160 reviews)

Sarasota “Executive Waterfront Suite” A hotel rm # 103 on Sara Bay Marina

Sarasota

8% off
£625
for 7 nights, 1 room
£89 per night
includes taxes & fees
Sarasota “Executive Waterfront Suite” A hotel rm # 103 on Sara Bay Marina
Living area
Beach
King bed
Arial view of the building - right on the beach!
Exceptional
(25 reviews)

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Siesta Key

8% off
£2,459
for 7 nights, 1 apartment
£351 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Pool
Beach chairs are offered for our guests in the private beach area of our complex
Property grounds
Terrace/patio
Exceptional
(99 reviews)

Great rates for September! SIESTA KEY GULF 2 bed 2 bath condo Jamaica Royale 104

Siesta Key

8% off
£3,147
for 7 nights, 1 apartment
£450 per night
includes taxes & fees
Great rates for September! SIESTA KEY GULF 2 bed 2 bath condo Jamaica Royale 104
Exterior detail
Private kitchen
Living area
Interior
Exceptional
(34 reviews)

Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!

Sarasota

7% off
£1,636
for 7 nights, 1 home
£234 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Property grounds
Marina
Private kitchen
Living area
Exceptional
(43 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
£2,113
for 7 nights, 1 apartment
£302 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Pool
Interior
Private kitchen
Interior
Exceptional
(28 reviews)

Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach

Sarasota

8% off
£2,456
for 7 nights, 1 home
£351 per night
includes taxes & fees
Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach
View of spacious main pool and clubhouse.  Dry sauna and gym inside.
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Enclosed patio brand new furniture (purchased June 2024)
Front Entrance
Exceptional
(102 reviews)

Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!

Siesta Key

5% off
£2,995
for 7 nights, 1 apartment
£428 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Dining table + 2 barstools for extra seating
Enclosed patio area with private pool
Property grounds
Pool
Exceptional
(57 reviews)

Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks

Sarasota

5% off
£2,393
for 7 nights, 1 home
£342 per night
includes taxes & fees
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in South Sarasota?
Prices for holiday rentals in South Sarasota vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in South Sarasota to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for South Sarasota holiday house rentals?
You can find great discounts on house rentals in South Sarasota on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any South Sarasota holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in South Sarasota with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in South Sarasota?
A long-stay holiday rental in South Sarasota is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit South Sarasota for a holiday rental?
The best time to visit South Sarasota for a holiday rental is during the peak season, which runs from January to March. This lively period attracts sun-seekers and outdoor enthusiasts eager to take advantage of the warm weather and beautiful beaches. With average temperatures ranging from 15 to 25 degrees Celsius, visitors can comfortably enjoy a variety of activities, including strolls along the sandy shores, exploring local parks, and indulging in the vibrant dining scene.March, in particular, is a popular month to visit South Sarasota. The weather is pleasantly warm, making it ideal for beach days, boating, and engaging in water sports. Additionally, this month often features exciting local events and festivals that showcase the area's rich culture and community spirit.For those seeking a more budget-friendly option, consider planning your trip in October. This month offers the opportunity to enjoy a quieter atmosphere while still experiencing the beauty of South Sarasota. With fewer crowds, you can take your time exploring the stunning coastline and local attractions without the hustle and bustle of peak season.Ultimately, the best time to visit South Sarasota will depend on whether you prefer the vibrancy of peak season or the tranquillity of the shoulder months.
How early should I book a South Sarasota holiday rental?
Book your South Sarasota holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in South Sarasota, Florida, United States of America?
In South Sarasota, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural offerings. The beautiful Siesta Key Beach, renowned for its powdery white sands and clear turquoise waters, is a must-visit for beach lovers. Nearby, the picturesque Siesta Key Village offers charming shops, restaurants, and vibrant nightlife, making it a great spot to unwind after a day at the beach.Another highlight is the Marie Selby Botanical Gardens, located along the bay, which features stunning tropical plants, beautiful gardens, and a lovely view of the waterfront. For those interested in arts and culture, the Ringling Museum of Art, situated a short drive away, showcases an impressive collection of art and exhibits, along with the historic Ca' d'Zan mansion and beautiful gardens.Additionally, the nearby Oscar Scherer State Park offers opportunities for hiking, bird watching, and enjoying Florida's natural landscape, while the Legacy Trail provides a scenic route for cycling and walking.
Can I change or cancel my South Sarasota home rental booking on Vrbo?
To find South Sarasota holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the South Sarasota holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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