Siesta Key Village Holiday Rentals
- Sarasota
- ·
- Siesta Key
- 2.7 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key Village
- 0.36 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 0.42 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key Village
- 0.18 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Pool
- Pet Friendly
- Kitchen
- Parking
- Sarasota
- ·
- Siesta Key
- 1.67 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key
- 1.12 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Sarasota
- ·
- Siesta Key
- 2.48 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Sarasota
- ·
- Siesta Key
- 0.67 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Luxury Holiday Rentals in Siesta Key Village
- Sarasota
- ·
- Siesta Key
- 0.50 mi to center
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
- Sarasota
- ·
- Siesta Key Village
- 0.35 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key Village
- 0.23 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Sarasota
- ·
- Siesta Key Village
- 0.20 mi to center
- View
- Pet Friendly
- Parking
- Internet
- Sarasota
- ·
- Siesta Key Village
- 0.12 mi to center
- View
- Parking
- Internet
- Child Friendly
- Sarasota
- ·
- Siesta Key
- 2.50 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Sarasota
- ·
- Siesta Key
- 0.36 mi to center
- Spa
- Fireplace/Heating
- Pool
- View
- Sarasota
- ·
- Siesta Key
- 2.56 mi to center
- Spa
- Fireplace/Heating
- Pool
- View
- Sarasota
- ·
- Siesta Key
- 2.51 mi to center
- Spa
- Fireplace/Heating
- Pool
- View
Top-Rated Holiday Rentals with a Pool in Siesta Key Village
- Sarasota
- ·
- Siesta Key Village
- 0.08 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 2.28 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key
- 2.43 mi to center
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Sarasota
- ·
- Siesta Key
- 1.15 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key
- 2.43 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key
- 1.43 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 2.29 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 1.15 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 2.43 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
Pet-Friendly Holiday Rentals in Siesta Key Village
- Sarasota
- ·
- Siesta Key Village
- 0.26 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Sarasota
- ·
- Siesta Key
- 2.74 mi to center
- View
- Pet Friendly
- Parking
- Internet
- Sarasota
- ·
- Siesta Key Village
- 0.17 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key Village
- 0.27 mi to center
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key Village
- 0.21 mi to center
- View
- Pet Friendly
- Parking
- Internet
- Sarasota
- ·
- Siesta Key
- 0.99 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
- Sarasota
- ·
- Siesta Key
- 2.54 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
- Sarasota
- ·
- Siesta Key
- 0.30 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key
- 0.32 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
Large Holiday Rentals and Private Villas in Siesta Key Village
- Sarasota
- ·
- Siesta Key Village
- 0.07 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
- Internet
- Child Friendly
- Sarasota
- ·
- Siesta Key
- 1.77 mi to center
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Sarasota
- ·
- Siesta Key Village
- 0.18 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Sarasota
- ·
- Siesta Key
- 0.82 mi to center
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
Wheelchair Accessible Holiday Homes in Siesta Key Village
- Sarasota
- ·
- Siesta Key
- 2.57 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
- Sarasota
- ·
- Siesta Key Village
- 0.13 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
- Sarasota
- ·
- Siesta Key
- 1.98 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key
- 0.48 mi to center
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
- Sarasota
- ·
- Siesta Key
- 1.52 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 1.51 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 1.52 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 0.97 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
Siesta Key Village Private Villas and Holiday Homes Under $200
- Sarasota
- ·
- Siesta Key
- 0.48 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- Fireplace/Heating
- View
- Parking
- Air Conditioner
- Sarasota
- ·
- Siesta Key
- 2.61 mi to center
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
- Sarasota
- ·
- Siesta Key
- 2.07 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Oceanfront
- Spa
- Fireplace/Heating
- Ocean View
- Sarasota
- ·
- Siesta Key
- 2.77 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 1.56 mi to center
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
- Sarasota
- ·
- Siesta Key
- 1.23 mi to center
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
- Sarasota
- ·
- Siesta Key
- 1.28 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
Instantly Bookable Holiday Homes in Siesta Key Village
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- Sarasota
- ·
- Siesta Key Village
- 0.14 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
- Sarasota
- ·
- Siesta Key Village
- 0.17 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Pool
- Kitchen
- Parking
- Air Conditioner
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- View
- Sarasota
- ·
- Siesta Key
- 1.92 mi to center
- Oceanfront
- Pool
- Ocean View
- View
Book a Last Minute Place to Stay in Siesta Key Village
About Casai's Private Villas and Holiday Rentals in Siesta Key Village
Discover more than 5827 vacation rentals available in Siesta Key Village. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Siesta Key Village.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Siesta Key Village, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Siesta Key Village. On average, places to stay near Siesta Key Village offer 966.32 ft², with nightly prices averaging US $553.
With Casai, finding and comparing holiday rentals in Siesta Key Village is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Siesta Key Village
| Type | Count |
|---|---|
| Vacation Homes | 1630 |
| Holiday Apartments | 567 |
| Villas | 364 |
| Cottages | 63 |
Use these Quick Filters to Find a Holiday Rental in Siesta Key Village
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Siesta Key Village.
Weather in Siesta Key Village, FL
View the weather forecast for Siesta Key Village before booking your Siesta Key Village Vacation Rentals to confirm your best time to go.
Frequently Asked Questions About Siesta Key Village?
What are the top holiday rentals in Siesta Key Village?
With numerous options available in Siesta Key Village, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Siesta Key Village:
- Across The Street From #1 Beach
- Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
- A Bayside Treasure - Outstanding Waterfront Views!
- The Inn On Siesta Key
- On Siesta Key Beach, View, pool, 2 Bed 2 Ba, plus pull out Queen,
- Full Gulf Views Across from Siesta Key Beach
- Spacious Penthouse Suite,3 Bd,3 Bth, Beachfront-Crescent Beach, May 16-23 Avail
- Siesta Key GULF SIDE-Peaceful Private Condo, 2 Bed 2 bath, Jamaica Royale #100
- 🦩Book Me Baby! Bayview Beauty at Siesta Key 🦩
- Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach
How many holiday rentals have private pools in Siesta Key Village?
Discover a selection of holiday rentals with private pools near Siesta Key Village with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- ON Siesta Key BEACH! Pool,Remodeled! 2bd2ba, sleeps 6, 3mins from door to sand
- The 19th Hole
- Lulu's Crescent Cottages - Entire two Unit Complex
- Exceptional Beachfront condo on Crescent Beach
Which holiday homes in Siesta Key Village are best for families?
If you're searching for a family-friendly holiday home in Siesta Key Village, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Siesta Key Village:
- Siesta Key Beach stay, pool & island shuttle stops
- Siesta Key Dream Inn Vacation Rental Near Village!
- Hidden Paradise by Beachside Management
How many Casai.com holiday rentals are available in Siesta Key Village?
As of 2026, Casai boasts over 5827 properties listed in the Siesta Key Village area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Siesta Key Village.









































































