Siesta Key holiday homes

We found 6,956 holiday rentals — enter your dates for availability
Discover a selection of 418 homes, 73 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:27 Nov - 4 Dec

nm
Kitchen area
Outdoor dining
Exterior detail
Exceptional
(242 reviews)

Great Value!!! Immaculate, minutes from the beach, With heated pool !!

Sarasota

5% off
NZ$3,069
for 7 nights, 1 home
NZ$438 per night
includes taxes & fees
Great Value!!! Immaculate, minutes from the beach, With heated pool !!
Terrace/patio
Interior
Room
Living area
Exceptional
(46 reviews)

🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown

Sarasota

7% off
NZ$1,983
for 7 nights, 1 home
NZ$283 per night
includes taxes & fees
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Private kitchen
Living area
Exterior
Pool
Exceptional
(5 reviews)

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

Siesta Key

17% off
NZ$32,813
for 7 nights, 1 home
NZ$4,688 per night
includes taxes & fees
Luxury Villa*Pool*Hot Tub*Dolphins*Close to Beach
Exterior
Private kitchen
Dining
Room
Exceptional
(11 reviews)

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

Siesta Key

7% off
NZ$14,935
for 7 nights, 1 home
NZ$2,134 per night
includes taxes & fees
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
Exterior
Dining
Private kitchen
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
NZ$9,374
for 7 nights, 1 home
NZ$1,339 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
Dining
Kitchen
Wonderful
(161 reviews)

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

Siesta Key

8% off
NZ$4,464
for 7 nights, 1 apartment
NZ$638 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
(107 reviews)

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

Siesta Key

6% off
NZ$4,113
for 7 nights, 1 apartment
NZ$588 per night
includes taxes & fees
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Large screen smart tv
Beautiful entrance to your private beach
Interior
Living area
Exceptional
(85 reviews)

Private Villa Beachside complex, Siesta Key private beach access 2br/2ba patio

Siesta Key

8% off
NZ$4,372
for 7 nights, 1 villa
NZ$625 per night
includes taxes & fees
Private Villa Beachside complex, Siesta Key private beach access 2br/2ba patio
Bedroom #2- Queen mattress
Terrace/patio
Private kitchen
Living area
Exceptional
(20 reviews)

Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape

Sarasota

8% off
NZ$2,087
for 7 nights, 1 home
NZ$298 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Arial view of the building - right on the beach!
Beach
Interior
Living area
Exceptional
(23 reviews)

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

Siesta Key

7% off
NZ$5,094
for 7 nights, 1 apartment
NZ$728 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Dining
Beach
Exterior
Property grounds
Wonderful
(16 reviews)

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

Siesta Key

8% off
NZ$4,935
for 7 nights, 1 apartment
NZ$705 per night
includes taxes & fees
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Property grounds
Sunset Royale Condominiums
Room
Interior
Exceptional
(52 reviews)

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

Siesta Key

8% off
NZ$3,538
for 7 nights, 1 apartment
NZ$505 per night
includes taxes & fees
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Private kitchen
Marina
Property grounds
Exterior
Exceptional
(38 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
NZ$4,621
for 7 nights, 1 apartment
NZ$660 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
New king bed
Front door and porch area
Beach
Robin Hood Rentals golf carts bikes etc
Exceptional
(15 reviews)

Siesta Key Village • Pool • Walk to Beach • Pets

Siesta Key

8% off
NZ$3,245
for 7 nights, 1 apartment
NZ$464 per night
includes taxes & fees
Siesta Key Village • Pool • Walk to Beach • Pets
Dining
Interior
Living area
Property grounds
Exceptional
(42 reviews)

Luxury condo located directly on Siesta Key Beach

Siesta Key

8% off
NZ$4,094
for 7 nights, 1 apartment
NZ$585 per night
includes taxes & fees
Luxury condo located directly on Siesta Key Beach
Living Room
Resort Area
Property grounds
Clubhouse
Exceptional
(62 reviews)

NEWLY REMODELED! On World Famous Crescent Beach

Siesta Key

5% off
NZ$3,685
for 7 nights, 1 apartment
NZ$526 per night
includes taxes & fees
NEWLY REMODELED! On World Famous Crescent Beach
New Queen Bed with plenty of pillows to choose to your liking.
Private rear patio
Living Room, makeup vanity or desk, and kitchen
Entry shelves with extra beach towels, cooler, futon blankets, etc
Exceptional
(20 reviews)

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

Siesta Key

5% off
NZ$3,593
for 7 nights, 1 apartment
NZ$513 per night
includes taxes & fees
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
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
NZ$5,801
for 7 nights, 1 apartment
NZ$829 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Pool
Enclosed patio area with private pool
Dining table + 2 barstools for extra seating
Property grounds
Exceptional
(55 reviews)

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

Sarasota

5% off
NZ$4,485
for 7 nights, 1 home
NZ$641 per night
includes taxes & fees
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Children’s area
Beach
fantastic pool with BBQ grill next to it
Interior
Exceptional
(88 reviews)

🌷Steps to Siesta Beach, Chic Studio, Pool & Patio

Siesta Key

8% off
NZ$4,193
for 7 nights, 1 apartment
NZ$599 per night
includes taxes & fees
🌷Steps to Siesta Beach, Chic Studio, Pool & Patio
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    Enjoy full kitchens, laundry, pools, gardens and more
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    More space, more privacy, more amenities — more value

Why visit Siesta Key

  • Stunning Beaches: Relax on the pristine, family-friendly beaches, especially the renowned Siesta Key Beach with its soft, white sands.
  • Vibrant Village: Explore the lively Siesta Key Village, filled with charming shops, restaurants, and a welcoming atmosphere.
  • Outdoor Activities: Enjoy a variety of outdoor adventures, from water sports to nature walks in the scenic parks and marina.
  • Relaxed Atmosphere: Experience the laid-back vibe perfect for leisurely days under the sun, ideal for families and couples alike.
  • Cultural Experiences: Immerse yourself in the local culture through events, art, and community gatherings throughout the area.

Top attractions in and around Siesta Key

Siesta Key is a stunning coastal city perfect for a family or outdoor holiday. Enjoy its beautiful beaches, urban parks, and marina that offer a blend of relaxation and a touch of city vibes. Whether you're exploring nature or taking in the local culture, Siesta Key provides an ideal backdrop for creating memorable experiences. This beachside haven is sure to charm every visitor with its unique blend of leisure and excitement.

  • Siesta Key Beach: Renowned for its powdery white sands and crystal-clear waters, Siesta Key Beach offers a relaxed atmosphere perfect for sunbathing, swimming, and beach games. The vibrant sunsets are a must-see.
  • St. Armands Circle: A charming shopping and dining district featuring unique boutiques, art galleries, and delightful eateries, St. Armands Circle presents a bustling city vibe where you can enjoy leisurely strolls.
  • Lido Beach: Known for its serene setting and natural beauty, Lido Beach provides a tranquil escape with opportunities for swimming, picnicking, and enjoying stunning coastal views.

Things to do recommended for couples

Discover Siesta Key’s charm with a sunset sail, hand in hand along pristine beaches, and a cosy seaside dinner. Enjoy the local flavours and vibrant arts scene, making every moment a treasure for you both.

Things to do recommended for families

Families can enjoy a variety of kid-friendly experiences in Siesta Key, such as building sandcastles on the famous Siesta Beach and exploring local marine life at the vibrant tide pools, perfect for a sun-soaked family adventure.

Things to do recommended for groups

Experience adventure on the TreeUmph. Adventure Course, a zipline and ropes course located 29km from Siesta Key. Perfect for group travellers seeking an outdoor thrill and local flavour in their holiday adventures.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Siesta Key

When planning your trip, whether you’re travelling with a group, family, pets, or seeking longer stays, be sure to use the appropriate filters that align with your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Siesta Key with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group get-togethers. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Siesta Key with young kids: Travelling with young kids can be quite a task. It's important to prioritise their comfort and safety, as well as having access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Siesta Key: For many, a family holiday isn’t complete without including their furry companion. If this describes you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Siesta Key: If you're in search of holiday rentals with great offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in and around Siesta Key

Siesta Key offers a relaxing tropical escape with its pristine, family-friendly beaches. Enjoy the golden sands of Siesta Key Beach and explore the vibrant Siesta Key Village, where the atmosphere is friendly and laid-back. Stroll along the picturesque Siesta Beach and savour the island’s unique charm, perfect for outdoor adventures and leisurely days under the sun.

  • Sarasota: Located approximately 8km from Siesta Key, Sarasota is a vibrant city known for its beautiful beaches and family-friendly atmosphere. Visitors can enjoy a blend of urban and coastal experiences, with plenty of shopping centres and recreational areas to explore. The city's cultural scene is rich, featuring galleries, theatres, and local markets. Notable landmarks include the stunning beaches that cater to families and beachgoers alike, as well as charming town neighbourhoods that offer a taste of local life. Sarasota is perfect for those looking to combine beach relaxation with urban adventures.
  • Siesta Key Village: Siesta Key Village is a charming neighbourhood located within Siesta Key, offering a delightful beach-themed experience. This area is known for its relaxed vibe, making it an ideal spot for families and visitors seeking leisure. With a variety of recreational areas, shopping centres, and local eateries, Siesta Key Village is a hub of activity. The famous Siesta Beach, renowned for its soft white sands, is just a stone's throw away, providing ample opportunity for sunbathing and water sports. The village encapsulates the spirit of coastal living, making it a must-visit destination.
  • Lido Key: Situated about 5km from Siesta Key, Lido Key is a picturesque island that offers a unique blend of beach and urban experiences. Known for its pristine beaches and family-friendly atmosphere, visitors can indulge in shopping and recreational activities within the area. Lido Key features beautiful urban parks and beach access, perfect for picnics and outdoor fun. The scenic views and relaxed pace of life make Lido Key an excellent choice for families and those looking to unwind while still having access to city attractions.

Best time to go to Siesta Key

If you're planning a trip to Siesta Key, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January62.6°F (17.0°C)Light RainMostly SunnyModerately High
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately High
April73.4°F (23.0°C)Light RainMostly SunnyAverage
May77.7°F (25.4°C)Light RainMostly SunnyAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverage
July82.9°F (28.3°C)Light RainMostly SunnyModerately High
August83.3°F (28.5°C)Light RainMostly SunnyAverage
September81.5°F (27.5°C)Light RainMostly SunnyAverage
October77.2°F (25.1°C)Light RainMostly SunnyModerately Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyModerately Low
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyModerately Low

Booking with Vrbo is a breeze

Looking to cut costs on your next getaway? Try being flexible with your travel dates, as prices can vary. Also, booking a longer stay might help you save significantly. To find the ideal Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's clever Trip Board offers you a dedicated area to plan new adventures, pick up right where you left off, or keep track of your travel arrangements. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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)
  • Siesta Key Beach Playground (1.1 mi / 1.7 km)
  • Shell Beach (1.6 mi / 2.6 km)
  • Crescent Beach (2.3 mi / 3.8 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 home accommodation in Siesta Key?
The most in-demand types of holiday homes in Siesta Key are condos. Want something different? Bookabach 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 home 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 Bookabach 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 home amenities in Siesta Key?
An electric car charging station, tennis and a garden top the list of most popular home amenities in Siesta Key. Whether you plan to travel solo, with your spouse or a group of friends, Bookabach can help you find a holiday home 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 homes 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 homes 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 Bookabach and stay connected on your holiday.
How old do you have to be to rent a holiday home in Siesta Key?
We recommend checking with the Siesta Key holiday home you're looking at on Bookabach as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday home 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 Bookabach'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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