South Sarasota holiday rentals

We found 6,955 holiday rentals — enter your dates for availability
Discover a selection of 37 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:8 Jan - 15 Jan

Living area
Exterior
Pool
Private kitchen
Exceptional
(28 reviews)

Rare private beachfront estate on the Gulf.

Nokomis

8% off
S$34,308
for 7 nights, 1 home
S$4,901 per night
includes taxes & fees
Rare private beachfront estate on the Gulf.
Outdoor dining
Living area
Interior
Exterior detail
Exceptional
(6 reviews)

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

Sarasota

8% off
S$11,909
for 7 nights, 1 home
S$1,701 per night
includes taxes & fees
New modern home with salt water heated pool located minutes from SiestaKey Beach
King bed
Beach
Arial view of the building - right on the beach!
Interior
Exceptional
(25 reviews)

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

Siesta Key

8% off
S$3,607
for 7 nights, 1 apartment
S$515 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Plenty of room to host an evening in
Sundeck on rooftop with partial ocean views
Living room with connected enclosed patio
Fireplace, large ceiling fan, and HDTV
Exceptional
(15 reviews)

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

Siesta Key

9% off
S$5,575
for 7 nights, 1 apartment
S$796 per night
includes taxes & fees
Sundeck with Ocean View, Private Access to Beach & 500ft to the Village
Interior
queen size bed
full size kitchen
Private kitchen
Excellent
(5 reviews)

Private Guesthouse Near Siesta Key & Downtown.

Sarasota

7% off
S$1,146
for 7 nights, 1 home
S$164 per night
includes taxes & fees
Private Guesthouse Near Siesta Key & Downtown.
Living area
Dining
Interior
Dining
Exceptional
(57 reviews)

Sarasota Waterfront Paradise- Location, Location...!!

Sarasota

8% off
S$4,159
for 7 nights, 1 home
S$594 per night
includes taxes & fees
Sarasota Waterfront Paradise- Location, Location...!!
Exterior
Outdoor dining
Room
Pool
Exceptional
(52 reviews)

LAKE SARASOTA VACATION HOME CABLE TV !!! Sport channels!

Sarasota

8% off
S$2,636
for 7 nights, 1 home
S$377 per night
includes taxes & fees
LAKE SARASOTA VACATION HOME CABLE TV !!! Sport channels!
Dining
Interior
Interior
Room
Exceptional
(45 reviews)

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

Sarasota

8% off
S$3,834
for 7 nights, 1 home
S$548 per night
includes taxes & fees
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Private, heated pool and spa with canal views and your own private dock.
Sophisticated and serene Mediterranean beach home.
Living area w/views of pool, jacuzzi and canal offering easy indoor-outdoor flow
Large dining room opens to living area, offering seamless entertaining space.
Exceptional
(14 reviews)

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

Siesta Key

7% off
S$9,471
for 7 nights, 1 home
S$1,353 per night
includes taxes & fees
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock
Indulge in serene relaxation at our inviting pool oasis!
Open-concept kitchen/living room—ideal for socializing in style.
Elegant dining room seats six, ideal for family meals.
Our fully equipped kitchen that gracefully opens up to the flex space.
Exceptional
(12 reviews)

Dog Friendly -4 Bed 2 Bath w/ HTD Pool (Sleeps 13)

Sarasota

6% off
S$5,773
for 7 nights, 1 home
S$825 per night
includes taxes & fees
Dog Friendly -4 Bed 2 Bath w/ HTD Pool (Sleeps 13)
Dining
BACKYARD OASIS WITH PRIVATE POOL
GREAT OUTDOOR SEATING AREA FOR THE WHOLE FAMILY TO ENJOY!
Living area
Exceptional
(52 reviews)

Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach

Siesta Key

8% off
S$10,713
for 7 nights, 1 home
S$1,530 per night
includes taxes & fees
Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach
Pool
additional bar area seating
Front (living) room
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
S$4,037
for 7 nights, 1 home
S$577 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
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
S$3,850
for 7 nights, 1 home
S$550 per night
includes taxes & fees
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Living area
5th floor view is spectacular!
Well Kept Pool for the exclusive use of Crescent Royale Owners and Guests
Interior
Exceptional
(79 reviews)

Top Floor Oceanfront View! Fantastic location! Saturday-Saturday only

Siesta Key

7% off
S$4,103
for 7 nights, 1 apartment
S$586 per night
includes taxes & fees
Top Floor Oceanfront View! Fantastic location! Saturday-Saturday only
Room
Private kitchen
Exterior detail
Living area
Exceptional
(34 reviews)

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

Sarasota

8% off
S$2,739
for 7 nights, 1 home
S$391 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Living area
Marina
Exterior
Private kitchen
Exceptional
(43 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,553
for 7 nights, 1 apartment
S$508 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Terrace/patio
Resort Styled 5-bdrm waterfront w/Pool/Spa/FirePit/Putting Grn/Boat/Jet Ski Lift
Exterior
2nd Floor Master w/Sliding door out to 2nd story Balcony
Wonderful
(17 reviews)

Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit

Bradenton

8% off
S$8,110
for 7 nights, 1 home
S$1,159 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Exterior detail
Private kitchen
Dining
Terrace/patio
Exceptional
(84 reviews)

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Sarasota

8% off
S$2,418
for 7 nights, 1 home
S$345 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Interior
Living area
Terrace/patio
Room
Exceptional
(134 reviews)

Lido Beach Walk! One block to beach!

Sarasota

8% off
S$2,036
for 7 nights, 1 room
S$291 per night
includes taxes & fees
Lido Beach Walk! One block to beach!
Terrace/patio
Living area
Dining Room
Interior
Exceptional
(22 reviews)

Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

Sarasota

16% off
S$3,448
for 7 nights, 1 villa
S$493 per night
includes taxes & fees
Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota
Interior
Sunset Royale Condominiums
Property grounds
Room
Exceptional
(53 reviews)

Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!

Siesta Key

8% off
S$2,939
for 7 nights, 1 apartment
S$420 per night
includes taxes & fees
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Glassed in and screened porch
Sports court
Interior
Terrace/patio
Exceptional
(185 reviews)

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key

7% off
S$2,982
for 7 nights, 1 apartment
S$426 per night
includes taxes & fees
Amazing 1 Br/1 Ba Condo at Casa Mar
Outdoor dining
Exterior
Dining
Private kitchen
Exceptional
(46 reviews)

Monthly Discounts will be reflected on your price quote.

Bradenton

9% off
S$1,304
for 7 nights, 1 home
S$186 per night
includes taxes & fees
Monthly Discounts will be reflected on your price quote.
Entry shelves with extra beach towels, cooler, futon blankets, etc
Private rear patio
New Queen Bed with plenty of pillows to choose to your liking.
Private kitchen
Exceptional
(22 reviews)

Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!

Siesta Key

8% off
S$3,675
for 7 nights, 1 apartment
S$525 per night
includes taxes & fees
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!

  • 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, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in South Sarasota?
Houses are the most popular kind of holiday rental in South Sarasota, according to our data. Even if you have a different idea in mind, Vrbo has holiday homes in a variety of shapes and sizes. Look through our options to find your perfect fit.
How much does it cost to rent a holiday rental in South Sarasota?
Season, length of stay and property type are among the factors that can influence the price of a holiday home. Simply click on your dates of travel to find your ideal escape. From comfy cottages to plush villas, all Vrbo holiday rentals offer terrific value.
How much does it cost to rent a beach house in South Sarasota?
When you travel and the style and size of the property will help determine the cost of your beachside escape. Enter your South Sarasota travel dates to view your options on Vrbo. Did someone just say "hot tub"? Use our filters to choose the features and amenities you need.
Are there pet-friendly holiday rentals in South Sarasota?
Yes. You can choose from 74 holiday rentals that cater to pets in South Sarasota. Several of our pet-friendly holiday rentals even come with an outdoor area for your furry friend to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Vrbo.
Can I rent a house with a pool in South Sarasota?
Check the "pool" box in our filter tool and choose from 40 houses with private pools in South Sarasota on Vrbo. Gentle soak, ball games or noodle joust? Free time is up to you when your holiday home has a swimming pool.
What are popular rental amenities in South Sarasota?
A chef, nearby museums and a water view head the list of most popular rental amenities in South Sarasota. Whether you're taking a trip solo, with a partner or as a family, Vrbo will help you find a holiday home that fits your style with all the features you need.
Are there large group holiday rentals in South Sarasota?
With 10 holiday rentals that can host 10 people or more in South Sarasota, you won't have to leave anyone off your invite list. From holidays with the extended family to special events like Christmas and birthday parties, Vrbo will help you find a large group rental to suit the occasion.
Are there holiday rentals in South Sarasota that welcome kids?
South Sarasota has 74 family-friendly holiday homes to pick from. And tracking down a stay that welcomes youngsters is super easy with Vrbo's "Properties good for families" filter. Besides having the whole place to yourselves, you'll also get amenities and perks like multiple bedrooms, pools and kitchens.
What are the top attractions for families in South Sarasota?
Keeping the kids amused during your stay in South Sarasota is a breeze with these family-friendly attractions:
  • Lido Beach
  • Mote Marine Laboratory & Aquarium
  • Sarasota Classic Car Museum
Are there one-bedroom holiday rentals in South Sarasota?
There are three one-bedroom properties in South Sarasota to select from. A one-bedroom holiday property is a superb choice if it's only you and your partner or if you're travelling alone. Throw in more space, convenience and privacy than a standard hotel, and you'll be sure to have an unforgettable trip.
Can I find two-bedroom holiday rentals in South Sarasota?
South Sarasota has 23 two-bedroom properties to choose from. Go for a holiday home with all the privacy and comfort you want at a price you'll love on Vrbo.
Are there holiday rentals with WiFi in South Sarasota?
South Sarasota has 29 holiday rentals with WiFi, so you'll be able to stay connected while you're on holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Vrbo homes will keep you online.
How can I find holiday rentals with air conditioning in South Sarasota?
South Sarasota has 72 holiday rentals where you can wind down in air-conditioned comfort. To book a stay on Vrbo that features this amenity, enter your preferred travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in South Sarasota?
Age restrictions can differ between properties on Vrbo, so look at the rules of the holiday rental in South Sarasota you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in South Sarasota for?
How long you can rent a holiday rental in South Sarasota is up to the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With a range of features like laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find a perfect place to call your home away from home in South Sarasota.

More holiday ideas