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

Siesta Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Siesta Key vacation rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,971 reviews)
"Amazing resort,"
United States
kurt
The price is ￥20,141
￥26,875 total
includes taxes & fees
Oct 18 - Oct 19
Tropical Beach Resorts
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (197 reviews)
"Best short vacation"
United States
Rommel
The price is ￥31,640
￥35,754 total
includes taxes & fees
Nov 8 - Nov 9
SeaSpray Resort
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,468 reviews)
"This place was perfect!"
United States
Kat
The price is ￥18,661
￥21,087 total
includes taxes & fees
Oct 21 - Oct 22
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,321 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is ￥27,086
￥33,291 total
includes taxes & fees
Oct 18 - Oct 19
Captiva Beach Resort
A compact living space with a kitchen, a dining area, and a sofa with cushions.

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 ￥8,590
￥31,067 total
includes taxes & fees
Oct 17 - Oct 18
Tiny House Siesta
A beach with a small cluster of palm trees in the foreground and a sandy beach extending to the horizon.

6. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (44 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 ￥17,777
￥48,962 total
includes taxes & fees
Oct 18 - Oct 19
[Beach Elements] pool view withprivate beach access
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

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 ￥22,060
￥48,444 total
includes taxes & fees
Oct 16 - Oct 17
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
An aerial view of a beach resort with a large sandy beach, a parking area, and a building complex with multiple structures.

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 ￥42,894
￥85,744 total
includes taxes & fees
Oct 15 - Oct 16
🌷Steps to Siesta Beach, Chic Studio, Pool & Patio
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

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 ￥17,299
￥58,198 total
includes taxes & fees
Oct 22 - Oct 23
Dolphin Villa | Pool | Steps to Siesta Key Village
Your own Private screened in lanai. Facing west for fantastic siesta key sunsets.

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 ￥19,793
￥55,222 total
includes taxes & fees
Oct 20 - Oct 21
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A beach with clear turquoise water and gentle waves.

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 ￥22,060
￥48,603 total
includes taxes & fees
Oct 17 - Oct 18
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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 ￥27,710
￥69,733 total
includes taxes & fees
Oct 15 - Oct 16
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

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 ￥13,536
￥47,818 total
includes taxes & fees
Oct 15 - Oct 16
[lounge like locals] walk to siesta beach +bikes
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

14. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (221 reviews)
"Nice stay perfect location"
United States
tom f.
The price is ￥19,808
￥74,613 total
includes taxes & fees
Oct 21 - Oct 22
Siesta beach....one and only
A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

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 ￥15,137
￥48,953 total
includes taxes & fees
Oct 15 - Oct 16
Siesta Heron Suites & Villas
A beach with waves and a bird flying near the shore.

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 ￥14,409
￥28,395 total
includes taxes & fees
Oct 15 - Oct 16
Tiny House Calypso with 1st floor sleeping
A beach with waves and a bird flying near the shore.

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 ￥13,776
￥27,680 total
includes taxes & fees
Oct 17 - Oct 18
The Mermaid at Tiny House Siesta
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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 ￥32,618
￥76,301 total
includes taxes & fees
Oct 15 - Oct 16
The Beach Club at Siesta Key #106A Resort by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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 ￥32,776
￥76,015 total
includes taxes & fees
Oct 18 - Oct 19
The Beach Club at Siesta Key #106D Resort by RVA
An aerial view of a beach resort with a large sandy beach, a parking area, and a building complex with multiple structures.

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 ￥51,461
￥96,059 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

The Capri at Siesta

The Capri at Siesta

10/10 Excellent
"Lovely location to visit"
Elijah 2-night trip
Posted 4 hours ago
The Capri at Siesta

Find out more about Siesta Key

Search for holiday rentals in Siesta Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Siesta Key using one of the methods below:

  • View our selection of featured holiday rentals in Siesta Key
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  • Enter your travel dates to view the best deals on holiday rentals in Siesta Key while they last

Look no further and take a look at our great range of rental properties in Siesta Key!

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.