Siesta Key Village holiday rentals

We found 1,137 holiday rentals — enter your dates for availability
Discover a selection of 119 homes, 28 apartments and other holiday rentals in Siesta Key Village that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, which might include parking and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Siesta Key Village

Showing deals for:27 Nov - 4 Dec

Room
Private kitchen
Exterior
Living area
Exceptional
(11 reviews)

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

Siesta Key

7% off
AU$12,494
for 7 nights, 1 home
AU$1,785 per night
includes taxes & fees
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
King bed
Beach
Interior
Living area
Exceptional
(23 reviews)

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

Siesta Key

7% off
AU$4,163
for 7 nights, 1 apartment
AU$595 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Exterior
Dining
Living area
Interior
Exceptional
(53 reviews)

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

Siesta Key

8% off
AU$7,701
for 7 nights, 1 home
AU$1,100 per night
includes taxes & fees
400 yards to Siesta Key Village, 800 yard To The public Beach Access 2 and 7.
Property grounds
Sunset Royale Condominiums
Interior
Room
Exceptional
(52 reviews)

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

Siesta Key

7% off
AU$2,764
for 7 nights, 1 apartment
AU$395 per night
includes taxes & fees
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Beach
Front door and porch area
Robin Hood Rentals golf carts bikes etc
New king bed
Exceptional
(15 reviews)

Siesta Key Village • Pool • Walk to Beach • Pets

Siesta Key

8% off
AU$2,704
for 7 nights, 1 apartment
AU$386 per night
includes taxes & fees
Siesta Key Village • Pool • Walk to Beach • Pets
fantastic pool with BBQ grill next to it
Beach
Children’s area
both duplexes belong together
Exceptional
(88 reviews)

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

Siesta Key

8% off
AU$3,487
for 7 nights, 1 apartment
AU$498 per night
includes taxes & fees
🌷Steps to Siesta Beach, Chic Studio, Pool & Patio

  • 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

When is the best time to visit Siesta Key Village for a holiday rental?
The best time to visit Siesta Key Village for a holiday rental is during the peak season from January to March. This period attracts sun-seekers and beach lovers keen to enjoy the warm, inviting weather, with temperatures typically ranging from 15 to 25 degrees Celsius. The beaches are vibrant, and the charming village buzzes with activity, offering a great blend of relaxation and fun.January, in particular, is a fantastic time to visit as it brings mild temperatures and a lively option. The stunning white sands of Siesta Key Beach are ideal for sunbathing, swimming, and various water sports, while the nearby shops and restaurants provide plenty of opportunities for exploration and indulgence.If you're looking for a more budget-friendly option, consider planning your trip in November. While this month is outside the peak tourist season, it still offers pleasant weather and a more tranquil experience, allowing you to enjoy the natural beauty and local charm without the crowds.
What are the top attractions in Siesta Key Village, Florida, United States of America?
In Siesta Key Village, visitors can enjoy a variety of attractions that highlight the area's charm and natural beauty. The famous Siesta Key Beach, known for its powdery white sand and crystal-clear waters, is a major draw, great for sunbathing, swimming, and beach volleyball. Close to the beach, the village itself offers a delightful selection of shops, restaurants, and cafes, creating a lively option for leisurely strolls.The Siesta Key Village frequently hosts local events, such as art fairs and live music performances, providing a vibrant community experience. Additionally, the nearby Point of Rocks on the southern end of Siesta Key Beach is a popular spot for snorkelling, where visitors can explore marine life in the shallows. For those interested in outdoor activities, the village's proximity to the scenic Legacy Trail offers opportunities for biking and walking through beautiful landscapes.
Are all fees included in the Siesta Key Village holiday homes prices shown on Stayz?
Stayz 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.
Are there any Siesta Key Village holiday homes with parking?
Stayz offers a wide selection of holiday homes in Siesta Key Village 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 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.
Are there any discounts for Siesta Key Village holiday homes?
You can find great discounts on holiday homes in Siesta Key Village on Stayz, 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.
Can I change or cancel my Siesta Key Village holiday home booking on Stayz?
To find Siesta Key Village holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Siesta Key Village?
A long-stay holiday home in Siesta Key Village 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Siesta Key Village holiday home?
Book your Siesta Key Village holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Siesta Key Village?
Prices for holiday homes in Siesta Key Village 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Siesta Key Village to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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