11 Vrbo Vacation Rentals On The Island Of Siesta Key - Updated 2024

vrbo siesta key
Catherine
Catherine 
Updated
| 4 min read

Siesta Key is an island in Sarasota County, Florida. It is a barrier island in the Gulf of Mexico and is popular among visitors who seek outdoor activities, such as swimming and sunbathing, because of its proximity to the beach and many more activities. Its many beaches offer different recreation amenities that appeal to all types of visitors from young ones to young at heart. It is truly a great getaway being close to many attractions and activities in one place, but to make it more perfect, let me guide with this list of the top HomeAway and Vrbo vacations rentals in Siesta Key that will surely provide optimal comfort and an unforgettable stay on this beautiful island. Let’s check it out!

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 03, 2024.

1. Beachside cottage perfect for six people (from USD 199)

At 1,000 square feet (92.9 square meters), this cottage features enough space for mid-sized groups with a maximum of six members. There are two queen-size beds, plus a Murphy bed, and the galley kitchen is equipped with stainless steel appliances. For your entertainment, there’s a 55-in smart television and WiFi access, so you can watch movies and shows in your spare time.

If you’re still looking for other entertainment options, you only have to head out. The beach is just a short walk away, so you can enjoy the sandy shores and cool seawater whenever you want. While you’re outside, you might want to see other well-known attractions in the area, such as Siesta Key Marina, Point of Rocks, and South Lido Park.

Stayed at this property?

425 meters (0.3 ft) from Siesta Key Drum Circle
145 reviews   Wifi Available
cottage 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
the murphy bed in the living room was perfect for our daughter
the kitchen and bathroom are nice with lots of room
the one thing we didn’t like was the lack of hand soap toilet paper and tissues
Cleanliness:
it was very clean
it was a very clean house
the unit does need a deep clean and cobwebs removed
the rooms were clean and they had great showers 10/10 would stay here again
clean modern and very close to the beach
Host:
rating details: the property manager was very helpful
Location:
the location of this property is terrific
the location is nice for beach access
reviewer comments: the location was perfect
great central location to explore the other gulf beaches
we had a great week here the location is perfect
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

2. Pleasant condo unit with access to resort-like amenities (from USD 210)

With three single beds and one king-size, this homey condo unit can comfortably accommodate five people. It also features a fully equipped kitchen for your dining needs. As for your entertainment, you can use any of the televisions available inside, or you might want to play board games with your companions.

Since this condo is part of Palm Bay Club, you’ll have access to many fantastic amenities. You can enjoy an hour of swimming in one of the two heated pools or play a game of tennis or pickleball on the court. Strolling on the beach is another great thing to do during your vacation. Once you’re done with all the activities for the day, soak in the hot tub to let your muscles rest.

Stayed at this property?

1.13 km (0.7 mi) from Siesta Key Drum Circle
181 reviews   Wifi Available
condo 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
the place was clean and comfortable with the pools and beach access as easy as can be
Cleanliness:
very clean and had everything we needed for our stay
the house was clean and comfortable (especially the master bed
Host:
very responsive and cordial
Location:
the location was a short walk to the beach which is nice
very close to the beach everything we needed was there loved it hope to stay there next year
everything is as described and easy to walk to all the attractions
super clean and comfortable unit great location will definately rent here again
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

3. Oceanfront condo unit with heated swimming pools (from USD 300)

With 1,350 square feet (125.42 square meters) of space, this condo unit features all the amenities to ensure that your vacation will be a memorable one. There are three beds, so up to six people can be accommodated here. But if you have more guests, you can use the sleeper sofa in the living room. Aside from the number of beds, you can find a 55-in television and internet connection. If you’re traveling with children, there are toys and games that they might love to play with.

This rental is located in front of a beach, so you only have to take a short walk to enjoy the white sand and the cool, blue waters. If you don’t like swimming in the ocean, you might prefer to dip in one of the heated pools instead.

Stayed at this property?

904 meters (0.6 ft) from Siesta Key Drum Circle
165 reviews   Wifi Available
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Cleanliness:
the beaches are clean
well appointed condo clean and as described online
the condo was really clean and stocked with everything we could possibly need for our stay
very clean with a great view
the beach is wide clean beautiful siesta key sand
Host:
another unique touch was a prepaid laundry card and laundry detergent which was thoughtful of the owner
lynn was very helpful when we had questions
Location:
the location of this unit is great
this location is absolutely beautiful love the beach
the location was so close to beach with a beautiful view
we enjoyed or vacation the location and the condo
close to the beach and pool lynn was responsive and helpful
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

4. Cozy condo unit in a prime location (from USD 220)

Even though this condo unit only has 581 square feet (53.98 square meters) of space, it’s still equipped well enough to accommodate solo travelers or couples. The bedroom features a plush queen-size bed, while the living room comes with a 55-in television, WiFi access, and a variety of games. As for your meals, feel free to whip out something delicious in the fully equipped kitchen.

If you’re not in the mood to cook, no worries because there are many restaurants nearby. While you’re out, you should take the opportunity to see a few beloved attractions, such as the beaches, South Lido Park, and Coconuts Family Entertainment Center.

Stayed at this property?

1.66 km (1.1 mi) from Siesta Key Drum Circle
152 reviews   Wifi Available
condo 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
bed was super comfortable too
Cleanliness:
the property itself was absolutely amazing impeccably clean
it was very clean and perfect location to beach and the village
great little condo decorated beautifully extremely clean and a perfect location to be able to walk to everything
Location:
great location within walking distance of the beach and everything
the location is excellent for beach access and siesta key village
place was immaculate and so cute we were within walking distance of everything including the beautiful beach
cute clean has everything you could possibly need including beach stuff very short walking to beach and restaurants
wonderfully decorated and appointed little house literally steps away from the beach and all the bars/restaurants/shops in siesta key
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

5. Bright and airy townhouse with private beach access (from USD 353)

Are you craving a beach getaway but don’t want to stay on a crowded beach? Then you might want to book this particular townhouse — especially since this rental comes with its own private beach. So, bring your best swimsuit and watersports gear, and have fun sunbathing on the sandy shores or swimming in the cool waters of the Gulf.

After a long, exciting day on the beach, head back to this rental to rest. Prepare a hearty meal in the kitchen to satisfy your hunger, then kick back on the sofa to watch a fun movie on the television. Since there’s free WiFi here, you can connect to your preferred streaming service to have more movie options.

Stayed at this property?

1.03 km (0.7 mi) from Siesta Key Drum Circle
146 reviews   Wifi Available
townhome 8 Guests 2 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Cleanliness:
the condo was very clean and updated
the condo was clean & well kept
the property was very clean and equipped with everything you need for your vacation
our condo was very clean and had easy access to the beach
the space is clean and fits the online description
Host:
the owner gave great recommendations on things to do
she is very nice and accommodating
varinia was a great host
everyone in the complex was so nice and friendly
the communication with the owner/host was great
Location:
the location is perfect
great location close to the beach easy walk
the location was fabulous with such easy access to the beach
the condo was short walk to the beach and close to restaurants and attractions
easy to book and varinia was very helpful great location on the beach
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

6. Cozy cottage for two near the beach (from USD 255)

Sitting right across the street from the beach, this cottage offers you quick access to beautiful views and many fun water activities including swimming, snorkeling, kayaking, and fishing. It’s perfect for couples or for solo adventurers as it can sleep up to two guests.

Air conditioning will keep you cool and cozy on a hot day. A cable TV and wireless internet access offer indoor entertainment. There are plenty of food options nearby but if you want to cook your own meals, there’s a fully equipped kitchen at your disposal.

Stayed at this property?
Siesta Key, Florida, United States
1.07 km (0.7 mi) from Siesta Key Drum Circle
cottage 2 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
thanks for having nice beach chairs umbrella and comfortable patio furniture
a nice living area with a little table to enjoy breakfast and do a little work
Cleanliness:
everything is very clean and up to date
the bed is very comfortable and the linens are good quality and very clean
the cottage was as described… clean comfy and had what we needed for a comfortable stay
Host:
the owners are very attentive & kind
Location:
you can walk there easily
great location for walking to the beach restaurants and shops
we had a great time the bikes were great location wonderful
we love this place & dogs are welcome which is very important to us
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

7. Luxury villa Siesta Key (from USD 780)

Let us start off with a luxurious accommodation that could fit 10 people. Its combination of white and blue interior gives you not just an island or beach ambiance but also one of Santorini, Greece. What’s nice about this house is its good location close to activities and attractions and you can have the pool all for yourself, of course, with family and friends. This is a great listing to bond with 10 people!

Stayed at this property?
Sarasota, Florida, United States
799 meters (0.5 ft) from Siesta Key Drum Circle
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 6 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
pool and hot tub are great
Host:
the local manager was super responsive
the property management was always friendly and available and quick to respond to any questions or concerns
the property manager was extremely helpful and nice
property manager was responsive and great to work with as was the owner
would recommend this property and definitely would stay with this host again did not want to leave
Location:
perfect location for a beach getaway with family
the walk into the village is a little bit more of a walk but definitely doable
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

8. Price alert – amazing new studio in downtown Siesta Village (from 129 USD)

This resort property is close to the beach, which is one block away. Aside from its nice location, this vacation rental has nice amenities, perfect for guests who want a hassle-free and comfortable stay. It’s 400 sq. ft. (37.1 sq m). The room is clean and large enough for families or friends travelling in groups of four. Be prepared for the many activities and attractions to choose from near the place.

Amazing New Studio in Downtown Siesta Village

Price: from 129 USD

Number of Guests: 4

Stayed at this property?

9. Next to Siesta Key Public Beach (from USD 180)

This property has a modern style that is really nice and classy. The combination of colors and furniture are not too complicated, yet still relaxing to the eyes and indeed relaxing to stay overnight. Most of the reviews say that this vacation rental has a good location and is close to the beach. Why not see for yourself and count? Who knows, maybe it’s just 59 steps!

Stayed at this property?

410 meters (0.3 ft) from Siesta Key Drum Circle
52 reviews   Wifi Available
Apartment 4 Guests 0 Bedrooms 1 Bathroom

Accommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the bed was comfortable and all the other furniture was in great shape
therefore at night it is necessary to run the ceiling fan to cool the room and sleep
the pool area is a serene oasis
Cleanliness:
the unit was very clean
the hide-a-way suite was very clean and comfortable
the hibiscus suite was very clean and nicely decorated
the grounds felt manicured and the room was clean and inviting
unit and complex is adorable and clean and well stocked with kitchen bath and beach necessities
Host:
and the manager/host was wonderful
we found virginia the proterty manager to be very helpful and responsiveness
any questions we had were answered immediately by virginia - she is so friendly and helpful
virginia was easy to communicate with and very accommodating as we ended up checking in earlier than expected
Location:
great location close to beach
love the location and the area cute place
we enjoyed this location very much
super location for the beach and the village
very good location nice pool had everything we needed
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

10. Beach views from all three floors! Royal Palm Suite (from USD 399)

This nice and spacious townhome is perfect for families or friends of up to 6 people travelling together. It’s like sleeping in your own house in Siesta Key. Guests staying in this accommodation may need to provide their own meals, but there is nothing to worry about since a kitchen is just around the corner. Feel free to make your own dishes with the available kitchen appliances just like in your own home!

Stayed at this property?

419 meters (0.3 ft) from Siesta Key Drum Circle
54 reviews   Wifi Available
townhome 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the deck off the living room/kitchen is a perfect spot for morning coffee and evening drinks
new amenities in the kitchen and squeaky clean
the master suite had huge closets and a very large bathroom
too many great things to do outside to bother with watching tv
Cleanliness:
super clean and quiet
everything is updated and was clean when we arrived
the property was extremely clean and everything worked perfectly
clean and updated space with a short walk to the beach
beautiful and clean easy 1/2 block walk to a beautiful beach
Host:
virginia (the manager was super helpful)
i would definitely recommend this property owner was very helpful and always available
Location:
we loved the location
it is the perfect location
beautiful place walk to the beach
we also enjoyed walking to siesta key village several times
this condo was the perfect place for a girlfriends weekend
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

11. Siesta Key Beach – honeymoon suite with gulf views (from USD 199)

Who wants to have a nice breakfast on a balcony where you can enjoy a great view of the ocean? Hands up for this great vacation spot! Feel the sand on your toes while being close to the beach. This townhome is fully furnished and equipped with all of the things that you could ever need. Beach chairs and umbrellas are available at no extra cost. It also features a beautiful heated black bottom waterfall pool for guests to enjoy.

Stayed at this property?

419 meters (0.3 ft) from Siesta Key Drum Circle
22 reviews   Wifi Available
townhome 4 Guests 1 Bedroom 2 Bathrooms

Accommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
it has the most comfortable furniture is quiet & clean
Cleanliness:
all it would have taken was some bleach to clean floors
Host:
management was very responsive and available too we loved our stay in the honeymoon suite
Location:
perfect location thanks virginia
the suite was perfect and so close to the beach
short walk to the most beautiful beach we've been to
very roomy had everything we needed and super close to beach shops and dining
had an amazing time kid friendly clean amazing location and great price
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Take me to the beach

It would really be a relaxing vacation if your vacation rental suits your budget and your taste, especially if you have the chance to be at the beach in a few minutes. A pleasurable stay with the kids and the whole family or maybe with friends and colleagues, Siesta Key has a lot to offer be it attractions, activities, and accommodations. I hope I was able to help you find a perfect place for you to have fun when you visit the island of Siesta Key!

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

History


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Catherine is a small-town woman who thrives in an ecstatic world, finding joy in planned and spontaneous travel. Life, to her, is a series of surprises waiting to be explored with open eyes....Read more

 Want to contribute as a Local Expert?
Explore Siesta Key
x
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.