Siesta Key holiday rentals

We found 6,909 holiday rentals — enter your dates for availability
Discover a selection of 400 homes, 74 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:11 Dec - 18 Dec

Large 8 person spa
Screened Lania
Living area
Shed for bikes and pool equipment
Exceptional
(21 reviews)

7 minute walk to Siesta Key beach. Large heated pool/spa. Very private.1/2 acre

Siesta Key

8% off
S$11,303
for 7 nights, 1 home
S$1,615 per night
includes taxes & fees
7 minute walk to Siesta Key beach. Large heated pool/spa. Very private.1/2 acre
Dining
Private kitchen
Living area
Room
Exceptional
(12 reviews)

Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!

Siesta Key

7% off
S$10,444
for 7 nights, 1 home
S$1,492 per night
includes taxes & fees
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
3RD LEVEL IS WHERE THE HOME IS LOCATED
BACKYARD OASIS WITH PRIVATE POOL
Private kitchen
BEDROOM #3 WITH KING SIZE BED & OWN BATHROOM AND SMART TV
Exceptional
(52 reviews)

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

Siesta Key

8% off
S$9,607
for 7 nights, 1 home
S$1,372 per night
includes taxes & fees
NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded
Private, heated pool and spa with canal views and your own private dock.
Sophisticated and serene Mediterranean beach home.
75" TV perfect for movie nights.
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$8,546
for 7 nights, 1 home
S$1,221 per night
includes taxes & fees
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock
Exterior
Dining
Interior
Living area
Exceptional
(53 reviews)

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

Siesta Key

8% off
S$6,979
for 7 nights, 1 home
S$997 per night
includes taxes & fees
400 yards to Siesta Key Village, 800 yard To The public Beach Access 2 and 7.
View from roof of pool, dock, hot tub
View of Sarasota Bay from balcony
Kitchen
Living room taken from master bedroom door
Wonderful
(161 reviews)

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

Siesta Key

8% off
S$3,417
for 7 nights, 1 apartment
S$488 per night
includes taxes & fees
Palm Bay Club Bayside Well-Priced Condo on Siesta Key 2 bed and 2 bath unit
activity area in main building
Kitchen renovated Fall 2013/Spring 2014
Room
Dining area from living area
Exceptional
(108 reviews)

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

Siesta Key

6% off
S$3,170
for 7 nights, 1 apartment
S$453 per night
includes taxes & fees
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Fully stocked kitchen
Screened porch
King bedroom
Swimming pool by the Gaming room
Exceptional
(44 reviews)

Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!

Siesta Key

6% off
S$3,567
for 7 nights, 1 room
S$510 per night
includes taxes & fees
Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
Property grounds
Beach
Property grounds
Dining
Wonderful
(16 reviews)

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

Siesta Key

8% off
S$3,733
for 7 nights, 1 apartment
S$533 per night
includes taxes & fees
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Interior
Beach
Arial view of the building - right on the beach!
King bed
Exceptional
(23 reviews)

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

Siesta Key

7% off
S$3,325
for 7 nights, 1 apartment
S$475 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Living room with smart tv
Dusk view of front of building
Robin Hood Rentals golf carts bikes etc
Living room with pullout couch
Exceptional
(15 reviews)

Siesta Key Village • Pool • Walk to Beach • Pets

Siesta Key

8% off
S$2,112
for 7 nights, 1 apartment
S$302 per night
includes taxes & fees
Siesta Key Village • Pool • Walk to Beach • Pets
Property grounds
Marina
Living area
Exterior
Exceptional
(39 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,499
for 7 nights, 1 apartment
S$500 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Terrace/patio
Sports court
Glassed in and screened porch
Exterior
Exceptional
(182 reviews)

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key

7% off
S$2,942
for 7 nights, 1 apartment
S$420 per night
includes taxes & fees
Amazing 1 Br/1 Ba Condo at Casa Mar
Property grounds
Resort Area
Living Room
Exterior
Exceptional
(62 reviews)

NEWLY REMODELED! On World Famous Crescent Beach

Siesta Key

5% off
S$2,805
for 7 nights, 1 apartment
S$401 per night
includes taxes & fees
NEWLY REMODELED! On World Famous Crescent Beach
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

7% off
S$2,477
for 7 nights, 1 apartment
S$354 per night
includes taxes & fees
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
View of spacious main pool and clubhouse.  Dry sauna and gym inside.
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Boat/Fishing Deck
Front Entrance
Exceptional
(102 reviews)

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

Siesta Key

5% off
S$4,389
for 7 nights, 1 apartment
S$627 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!

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)
  • Crescent Beach (2.3 mi / 3.8 km)
  • Point of Rocks (2.7 mi / 4.3 km)
  • Marie Selby Botanical Gardens (3.9 mi / 6.2 km)
  • Turtle Beach (4.4 mi / 7.1 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.

More holiday ideas