Siesta Key Vacation Rentals

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Vacation Rentals in Siesta Key

Room amenity
Siesta Key Island Rentals
3.0 star property
10.0 out of 10, Exceptional, (12)
"15 minute or less walk to everything you need. "
Siesta Key Island Rentals
Fridge, microwave, oven, stovetop
Siesta Key Studio - on the BEACH!
10.0 out of 10, Exceptional, (34)
"my friend and I were looking for a relaxing week right by siesta beach, and this place made it all possible. the hosts were incredibly accommodating and there were so many items they provided that I wouldn’t have even thought to bring but we ended up needing. communication was excellent, and they are both so sweet! literally steps away from the beach and the pool was so lovely as well."
Siesta Key Studio - on the BEACH!
Beach
Across The Street From #1 Beach
10.0 out of 10, Exceptional, (301)
"Amazing cottage! Just perfect for my husband and I to celebrate our anniversary. Very clean and super short walk to beach acces. Can watch the sunset every night if you desire. Highly recommend!!! We will make this a destination again in the future."
Across The Street From #1 Beach
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Outdoor pool, a heated pool
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
10.0 out of 10, Exceptional, (30)
"This home was perfect! Right across the street from the beach, large enough for our family of 6 and friends to stay, beautifully decorated, comfortable to hang out both inside and in the pool area. The owners thought of everything to make this home comfortable for guests. I would highly recommend this home and will definitely be returning."
Amazing Ocean Views, Steps to Beach, Pool w/ Waterslide, 6 Hole Mini Golf Course
Pool
New Luxury Home with Private Pool and Waterslide: 1 Minute Walk to the Beach!
10.0 out of 10, Exceptional, (13)
"Amazing stay! We couldn’t have asked for a better house. Clean, neat, amazing pool and accommodations, they basically provide everything. The rooftop view over looks the beach and the house has numerous balconies and outside space. The location is a block from the beach and a few minute walk to downtown siesta key. I have nothing but praise for this property and the property manager."
New Luxury Home with Private Pool and Waterslide: 1 Minute Walk to the Beach!
Outdoor pool, a heated pool
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US
10.0 out of 10, Exceptional, (106)
"Beautiful condo, wonderful location! We hope to return"
WOW Factor Exceptional Siesta Key Condo in a slice of Paradise on #1 Beach in US
Outdoor pool, a heated pool
2 BR/2 BA Condo on Siesta Key
9.8 out of 10, Exceptional, (17)
"Such a wonderful time! Quick walk to the beach! Trolly transportation was amazing!!"
2 BR/2 BA Condo on Siesta Key
On the beach, sun loungers, beach towels
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
9.8 out of 10, Exceptional, (189)
"We really enjoyed our stay. We were so close to the beach, it being private was great. Chairs are available to bring down on the beach but you don’t have to bring them back which was awesome. Great communication. Would definitely stay again."
The price is CA $543
CA $1,081 total
includes taxes & fees
Jun 17 - Jun 18
Super clean comfortable Modern Townhouse, Steps From PRIVATE Beach. 3 night min
On the beach, sun loungers, beach umbrellas, beach towels
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
9.8 out of 10, Exceptional, (118)
"Excellent vacation property right at the beautiful Siesta beach. We've rented both units, so we had the whole house and pool area all to ourselves. All details in the house are well though through, house is extremely clean and quiet. Large bedroms wth comfortable beds and plenty of common space in the front unit, smaller space in the back unit. Variety of food delivery options from restaurants in the area. The beach is short stroll away, my 82 yrs old mom was easily making the walk without her...
The price is CA $2,077
CA $4,043 total
includes taxes & fees
Jun 16 - Jun 17
SIESTA KEY LUXURY BEACH HOME, 80 STEPS to BEACH, RESORT POOL, 6 BED
Sports facility
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (159)
"Great property for families! Front desk staff and managers were accommodating when a family emergency took place. Would recommend and will be back. "
The price is CA $607
CA $740 total
includes taxes & fees
May 20 - May 21
The Residences at Siesta Key Beach by Hyatt Vacation Club
Beach nearby, sun loungers, beach towels
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
9.6 out of 10, Exceptional, (98)
"My wife and I spent four days at the Gull. The location is excellent. Just around the corner and you are on the beach. Just one block walk and you are in Siesta Key old town eating and shopping. The air conditioning is a little different. Utilizing widow units and portable units. The portable unit’s exhaust air causing the bungalow to be in a huge negative. This causes a lot of hot attic air to be drawn in around the pocket door to the master bedroom. Overall we really enjoyed our stay and the...
Siesta Key- 2 Bed/1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Beach nearby, sun loungers, beach towels
Siesta Key Village-Suite #3: A Block to the Beach!
9.6 out of 10, Exceptional, (24)
Siesta Key Village-Suite #3: A Block to the Beach!
Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4350)
"Very easy check in. Friendly staff"
The price is CA $169
CA $221 total
includes taxes & fees
May 21 - May 22
Tropical Beach Resorts
Property grounds
Luxury Home w/ Heated Pool and Private Beach Access
9.4 out of 10, Exceptional, (88)
"Our family stayed here and found it to be a very clean and well kept property. The private beach access was great. The pool gets very little sun, but still nice."
Luxury Home w/ Heated Pool and Private Beach Access
A heated pool
Lower Pricing! Private Beach, Pools, Bay Sunrises
9.4 out of 10, Exceptional, (79)
"We would definitely come again"
Lower Pricing! Private Beach, Pools, Bay Sunrises
Beach nearby, white sand, sun loungers, beach umbrellas
Siesta Palms By the Beach
3.5 star property
9.2 out of 10, Wonderful, (95)
"Everything perfect!!!!"
Siesta Palms By the Beach
Beach nearby, sun loungers, beach towels
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
9.2 out of 10, Wonderful, (39)
"Very clean place. Everything was provided. Close location to everything. My girlfriend and I had a great stay."
Siesta Key Condo- walk to beautiful beaches, ride a free trolley around the key
On the beach
Surfs Up on Siesta Beach, Beachside Condo
9.2 out of 10, Wonderful, (51)
"We really enjoyed this place and the location is perfect. I look forward to booking again."
Surfs Up on Siesta Beach, Beachside Condo
Beach nearby
A few steps from the beach with community pool
9.2 out of 10, Wonderful, (27)
"Enjoyed our visit and condo was terrific."
A few steps from the beach with community pool
A heated pool
Jamaica Royale Siesta Key Condo 109
9.2 out of 10, Wonderful, (22)
"8 minute walk to in my favorite beach. Easy to communicate with Michelle, she responded immediately to a question I had. Everything as posted on VRBO. Pool perfect temperature!"
Jamaica Royale Siesta Key Condo 109
Don't see what you're looking for?
See all available properties in Siesta Key
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.

Other types of properties in Siesta Key you may be interested in

Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4350)
"Very easy check in. Friendly staff"
The price is CA $169
CA $221 total
includes taxes & fees
May 21 - May 22
Tropical Beach Resorts
Lobby sitting area
Tropical Breeze Resort
3.0 star property
9.0 out of 10, Wonderful, (1001)
"This is in a very good location as it is within walking distance of the beach and Main Street. It is steps away from the many restaurants and shopping in the area. The cottage was clean and cozy. The staff was very accommodating and helpful. I would definitely stay there again. "
The price is CA $371
CA $469 total
includes taxes & fees
May 19 - May 20
Tropical Breeze Resort
Outdoor pool, sun loungers
Siesta Key Beach Resort and Suites
2.5 star property
8.8 out of 10, Excellent, (1004)
"Very clean, up to date, close to the beach and local restaurants. "
The price is CA $282
CA $385 total
includes taxes & fees
May 19 - May 20
Siesta Key Beach Resort and Suites
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.

Everything you need to know about Siesta Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Siesta Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Siesta Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Siesta Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Siesta Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Siesta Key vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Siesta Key vacation rentals we have selected for you start as low as CA $150 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Siesta Key rentals

At Expedia, we put the best Siesta Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Siesta Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Siesta Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Siesta Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Jim Neville Marine Preserve, 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 KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B.

How many vacation rentals are there in Siesta Key?

With 741 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. You’ll find favorite places to visit like Lido Beach and St. Armands Circle in the larger area.

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.

Recent reviews of Siesta Key properties
Expedia verified reviews