Siesta Key holiday rentals

We found 6,942 holiday rentals — enter your dates for availability
Discover a selection of 421 homes, 80 apartments and other holiday rentals in Siesta Key that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as a garden and pool. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Siesta Key

Showing deals for:13 Nov - 20 Nov

LARGE KITCHEN & LIVING AREA
Private kitchen
BACKYARD OASIS WITH PRIVATE POOL
MASTER BEDROOM WITH BALCONY ACCESS
Exceptional
(51 reviews)

NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded

Siesta Key

8% off
S$9,836
for 7 nights, 1 home
S$1,405 per night
includes taxes & fees
NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded
Exterior
Living area
Pool
Exterior
Exceptional
(5 reviews)

Luxury Villa*Pool*Hot Tub*Dolphins*Close to Beach

Siesta Key

17% off
S$24,176
for 7 nights, 1 home
S$3,454 per night
includes taxes & fees
Luxury Villa*Pool*Hot Tub*Dolphins*Close to Beach
View from roof of pool, dock, hot tub
View of Sarasota Bay from balcony
Living room taken from master bedroom door
Dining
Wonderful
(160 reviews)

Palm Bay Club Bayside Well-Priced Condo on Siesta Key 2 bed and 2 bath unit

Siesta Key

8% off
S$3,409
for 7 nights, 1 apartment
S$487 per night
includes taxes & fees
Palm Bay Club Bayside Well-Priced Condo on Siesta Key 2 bed and 2 bath unit
Private kitchen
Dining
Interior
Exterior
Exceptional
(53 reviews)

400 yards to Siesta Key Village, 800 yard To The public Beach Access 2 and 7.

Siesta Key

8% off
S$7,003
for 7 nights, 1 home
S$1,000 per night
includes taxes & fees
400 yards to Siesta Key Village, 800 yard To The public Beach Access 2 and 7.
activity area in main building
Kitchen renovated Fall 2013/Spring 2014
Room
Dining area from living area
Exceptional
(107 reviews)

Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price

Siesta Key

6% off
S$3,193
for 7 nights, 1 apartment
S$456 per night
includes taxes & fees
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Living area
Living area
Dining
Pool
Exceptional
(6 reviews)

Luxurious Sarasota Home with Pool

Siesta Key

8% off
S$6,012
for 7 nights, 1 home
S$859 per night
includes taxes & fees
Luxurious Sarasota Home with Pool
Property grounds
Beach
Dining
Property grounds
Wonderful
(16 reviews)

Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach

Siesta Key

8% off
S$3,777
for 7 nights, 1 apartment
S$540 per night
includes taxes & fees
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Beach
Interior
Room
Living area
Exceptional
(30 reviews)

Beach front paradise located in a Condo Building Beach front Penthouse!

Siesta Key

8% off
S$5,912
for 7 nights, 1 home
S$845 per night
includes taxes & fees
Beach front paradise located in a Condo Building Beach front Penthouse!
Living room
Front of building
Smart tv in second bedroom
Dining room table and full kitchen
Exceptional
(15 reviews)

A+ location clean 2 BR condo w pool arcade pets ok

Siesta Key

8% off
S$2,498
for 7 nights, 1 apartment
S$357 per night
includes taxes & fees
A+ location clean 2 BR condo w pool arcade pets ok
Living area
Living area
Private kitchen
Room
Exceptional
(62 reviews)

Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”

Siesta Key

8% off
S$3,720
for 7 nights, 1 apartment
S$531 per night
includes taxes & fees
Penthouse suite with ocean views 2Br 2 Bath “Great sunsets from lanai”
Property grounds
Marina
Exterior
Living area
Exceptional
(37 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,533
for 7 nights, 1 apartment
S$505 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Exterior
Marina
Dining
Pool
Exceptional
(6 reviews)

Renovated Siesta Key Condo, beach/heated pool access

Siesta Key

8% off
S$3,533
for 7 nights, 1 apartment
S$505 per night
includes taxes & fees
Renovated Siesta Key Condo, beach/heated pool access
Interior
Sports court
Glassed in and screened porch
Exterior
Exceptional
(181 reviews)

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key

7% off
S$3,008
for 7 nights, 1 apartment
S$430 per night
includes taxes & fees
Amazing 1 Br/1 Ba Condo at Casa Mar
Front Entrance
Quiet and safe neighborhood for families to swim, walk, bike, and fish
View of spacious main pool and clubhouse.  Dry sauna and gym inside.
Boat/Fishing Deck
Exceptional
(101 reviews)

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

Siesta Key

5% off
S$3,293
for 7 nights, 1 apartment
S$470 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
  • 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

Why people love visiting lively Siesta Key

Enjoy the live music and other features of Siesta Key. Well known for its beaches, seaside and sporting events, this relaxing city won't disappoint. Siesta Key Beach and Lido Beach are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Siesta Key

Are you hoping to discover top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Siesta Key a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mote Marine Laboratory & Aquarium (4.1 mi / 6.6 km)
  • Sarasota Jungle Gardens (6.4 mi / 10.3 km)
  • Premier Sports Campus at Lakewood Ranch (15.7 mi / 25.2 km)
  • Links on Longboat (4.3 mi / 6.9 km)
  • Harborside Golf Course at Longboat Key Club (4.3 mi / 7 km)
  • Stoneybrook Golf & Country Club (6.5 mi / 10.5 km)

Exploring the beaches and other natural features in Siesta Key

Travellers enjoy Siesta Key for its sunsets, seaside and tropical setting. Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Siesta Key is a great spot to appreciate mother nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Siesta Key Beach (0.9 mi / 1.5 km)
  • Lido Beach (2.4 mi / 3.9 km)
  • Venice Beach (14.1 mi / 22.7 km)
  • Shell Beach (1.6 mi / 2.6 km)
  • Crescent Beach (2.3 mi / 3.8 km)
  • Point of Rocks (2.7 mi / 4.3 km)

Seasonal weather in Siesta Key

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 28°C.

Transport to and around Siesta Key

The nearest airport is in Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), located 7.8 mi (12.5 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Siesta Key?
The most in-demand types of holiday rentals in Siesta Key are condos. Want something different? Vrbo has plenty of options to match the needs of our guests, so you'll see holiday properties in all sizes, and for all budgets. The perfect fit is waiting for you — discover yours today.
How much does it cost to rent a holiday rental in Siesta Key?
The average price for a holiday home in Siesta Key is determined by a number of factors, such as length of stay, property type and season. Whether you're thinking about a sprawling villa with space for the whole family or a cosy cabin for just you and the kids, just enter your travel dates to see stays that offer great value.
How much does it cost to rent a beach house in Siesta Key?
Prices for beach houses in Siesta Key can vary depending on the size and type of the property and time of year you're travelling. All you have to do is enter your travel dates into Vrbo and how many guests to see available options and prices. From there you can use the filters to narrow your search by ratings, amenities and more.
What are popular rental amenities in Siesta Key?
An electric car charging station, tennis and a garden top the list of most popular rental amenities in Siesta Key. Whether you plan to travel solo, with your spouse or a group of friends, Vrbo can help you find a holiday rental that fits your style with all the features you need.
What are the top attractions for families in Siesta Key?
Keep your kids busy at these leading family-friendly attractions in Siesta Key:
  • Siesta Key Beach
  • Lido Beach
  • Turtle Beach
Can I find two-bedroom holiday rentals in Siesta Key?
Gather your loved ones and enjoy a relaxing escape in one of the 1,076 two-bedroom holiday properties Siesta Key has to offer.
Are there holiday rentals with WiFi in Siesta Key?
Whether you'd like to keep up with the headlines, write a few emails or surf social media, there are 403 holiday homes with WiFi in Siesta Key. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How old do you have to be to rent a holiday rental in Siesta Key?
We recommend checking with the Siesta Key holiday home you're looking at on Vrbo as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Siesta Key for?
It really depends on the Siesta Key property. To see all available options offering extended stays, simply type your travel dates and number of people into Vrbo's search page. You can look forward to having the entire place to yourself, along with the comforts of home like air conditioning, a fully-equipped kitchen and outdoor spaces to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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