A yellow lifeguard tower with an American flag on a beach with people and umbrellas.

Siesta Key Vacation Rentals

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Our top choices for Siesta Key vacation rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,963 reviews)
"Amazing resort,"
United States
kurt
The price is CA $181
CA $242 total
includes taxes & fees
Oct 14 - Oct 15
Tropical Beach Resorts

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (193 reviews)
"Best short vacation"
United States
Rommel
The price is CA $278
CA $314 total
includes taxes & fees
Nov 2 - Nov 3
SeaSpray Resort

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,467 reviews)
"This place was perfect!"
United States
Kat
The price is CA $177
CA $200 total
includes taxes & fees
Oct 21 - Oct 22
Hibiscus Suites - Gateway to Siesta Key

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,319 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is CA $223
CA $276 total
includes taxes & fees
Oct 12 - Oct 13
Captiva Beach Resort

5. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is CA $82
CA $285 total
includes taxes & fees
Oct 16 - Oct 17
Tiny House Siesta

6. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (43 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is CA $178
CA $471 total
includes taxes & fees
Oct 26 - Oct 27
[Beach Elements] pool view withprivate beach access

7. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is CA $229
CA $481 total
includes taxes & fees
Oct 16 - Oct 17
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

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

🌷Steps to Siesta Beach, Chic Studio, Pool & Patio
Siesta Key
9.6 out of 10, Exceptional, (89 reviews)
"Great time in siesta key for a long weekend. Have stayed at this property many times. Always great experience and location to the beach and short walk into the village"
United States
Colleen O.
The price is CA $386
CA $776 total
includes taxes & fees
Oct 12 - Oct 13
🌷Steps to Siesta Beach, Chic Studio, Pool & Patio

9. Dolphin Villa | Pool | Steps to Siesta Key Village

Dolphin Villa | Pool | Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is CA $139
CA $505 total
includes taxes & fees
Oct 13 - Oct 14
Dolphin Villa | Pool | Steps to Siesta Key Village

10. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is CA $141
CA $452 total
includes taxes & fees
Oct 12 - Oct 13
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

11. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (55 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
The price is CA $137
CA $364 total
includes taxes & fees
Oct 12 - Oct 13
Siesta Key, Sea Horse Villa, Pool. Daily rentals

12. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
9.0 out of 10, Wonderful, (81 reviews)
"Good"
United States
Gelsy
The price is CA $284
CA $676 total
includes taxes & fees
Oct 13 - Oct 14
2BR Beach Style w Pool Beach Club Siesta 204C RVA

13. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is CA $101
CA $404 total
includes taxes & fees
Oct 13 - Oct 14
[lounge like locals] walk to siesta beach +bikes

14. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (220 reviews)
"Nice stay perfect location"
United States
tom f.
The price is CA $173
CA $666 total
includes taxes & fees
Oct 13 - Oct 14
Siesta beach....one and only

15. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $116
CA $418 total
includes taxes & fees
Oct 13 - Oct 14
Siesta Heron Suites & Villas

16. Tiny House Calypso with 1st floor sleeping

Tiny House Calypso with 1st floor sleeping
Sarasota
9.0 out of 10, Wonderful, (11 reviews)
"Third time here and best visit will book again in future "
United States
Desirae
The price is CA $128
CA $254 total
includes taxes & fees
Oct 12 - Oct 13
Tiny House Calypso with 1st floor sleeping

17. The Mermaid at Tiny House Siesta

The Mermaid at Tiny House Siesta
Sarasota
10.0 out of 10, Exceptional, (4 reviews)
"Traveled with my kids and this place was so great! Super cute and comfortable. We loved the Mermaid Tiny House."
United States
Kadina A.
The price is CA $124
CA $249 total
includes taxes & fees
Oct 12 - Oct 13
The Mermaid at Tiny House Siesta

18. The Beach Club at Siesta Key #106A Resort by RVA

The Beach Club at Siesta Key #106A Resort by RVA
South Village
9.0 out of 10, Wonderful, (68 reviews)
"Our family had a blast - great beach and pools."
United States
Nicholas M.
The price is CA $278
CA $669 total
includes taxes & fees
Oct 12 - Oct 13
The Beach Club at Siesta Key #106A Resort by RVA

19. The Beach Club at Siesta Key #106D Resort by RVA

The Beach Club at Siesta Key #106D Resort by RVA
South Village
9.4 out of 10, Exceptional, (63 reviews)
"Everything was great. It was a good location to the beach."
United States
Angela A.
The price is CA $295
CA $693 total
includes taxes & fees
Oct 12 - Oct 13
The Beach Club at Siesta Key #106D Resort by RVA

20. 🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach

🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach
Siesta Key
9.6 out of 10, Exceptional, (105 reviews)
"Very close to the beach and convenient. Clean. Easy for my fiance and I for a couple of days"
United States
Courtney
The price is CA $463
CA $875 total
includes taxes & fees
Oct 17 - Oct 18
🌷 Stunning 1-Bedroom Apartment Overlooking Pool, steps to Siesta Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siesta Key Hotel Reviews

Find out more about Siesta Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Siesta Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Siesta Key?

Yes, we give you a choice of vacation rentals in Siesta Key close to St. Boniface Episcopal Church Labyrinth, or you can go with a more secluded option if you'd like a relaxing place to stay. Visitors to Siesta Key like the popular beaches and live music. You can also check out the entertainment venues while you're visiting.

What are some of the best vacation rentals in Siesta Key?

Siesta Key Island Rentals: Visitors give good reviews to this Siesta Key vacation home rental, which comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Siesta Key is Siesta Heron Suites & Villas.

How many vacation rentals are there in Siesta Key?

With 401 Expedia vacation rentals, you're sure to find just the right place for your Siesta Key stay.

What can I see and do in Siesta Key?

Siesta Key Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jim Neville Marine Preserve. While here, Safe Harbor Siesta Key and Point of Rocks are other places worth a visit.

What are vacation rentals like in Siesta Key?

Vacation rentals are private accommodations you can stay in for several days or longer in Siesta Key. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.