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 September 01, 2025.
1. Beachside cottage perfect for six people (from USD 508)
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.
Sarasota, Florida, United States
425 meters (0.3 ft) from Siesta Key Drum Circle
Top guest reviews
Host:
rating details: the property manager was very helpfulLocation:
the location of this property is terrificthe location is nice for beach accessreviewer comments: the location was perfectgreat central location to explore the other gulf beacheswe had a great week here the location is perfectCleanliness:
it was very cleanit was a very clean housethe unit does need a deep clean and cobwebs removedthe rooms were clean and they had great showers 10/10 would stay here againclean modern and very close to the beachRead more reviewsAmenities & Room:
the murphy bed in the living room was perfect for our daughterthe kitchen and bathroom are nice with lots of roomthe one thing we didn’t like was the lack of hand soap toilet paper and tissues
2. Pleasant condo unit with access to resort-like amenities (from USD 392)
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.
Siesta Key, Florida, United States
1.13 km (0.7 mi) from Siesta Key Drum Circle
Top guest reviews
Host:
very responsive and cordialLocation:
the location was a short walk to the beach which is nicevery close to the beach everything we needed was there loved it hope to stay there next yeareverything is as described and easy to walk to all the attractionssuper clean and comfortable unit great location will definately rent here againCleanliness:
very clean and had everything we needed for our staythe house was clean and comfortable (especially the master bedRead more reviewsAmenities & Room:
the place was clean and comfortable with the pools and beach access as easy as can be
3. Oceanfront condo unit with heated swimming pools (from USD 412)
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.
Sarasota, Florida, United States
904 meters (0.6 ft) from Siesta Key Drum Circle
Top guest reviews
Host:
another unique touch was a prepaid laundry card and laundry detergent which was thoughtful of the ownerlynn was very helpful when we had questionsLocation:
the location of this unit is greatthis location is absolutely beautiful love the beachthe location was so close to beach with a beautiful viewwe enjoyed or vacation the location and the condoclose to the beach and pool lynn was responsive and helpfulRead more reviewsCleanliness:
the beaches are cleanwell appointed condo clean and as described onlinethe condo was really clean and stocked with everything we could possibly need for our stayvery clean with a great viewthe beach is wide clean beautiful siesta key sand
4. Cozy condo unit in a prime location (from USD 333)
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.
Siesta Key, Florida, United States
1.66 km (1.1 mi) from Siesta Key Drum Circle
Top guest reviews
Location:
great location within walking distance of the beach and everythingthe location is excellent for beach access and siesta key villageplace was immaculate and so cute we were within walking distance of everything including the beautiful beachcute clean has everything you could possibly need including beach stuff very short walking to beach and restaurantswonderfully decorated and appointed little house literally steps away from the beach and all the bars/restaurants/shops in siesta keyCleanliness:
the property itself was absolutely amazing impeccably cleanit was very clean and perfect location to beach and the villagegreat little condo decorated beautifully extremely clean and a perfect location to be able to walk to everythingRead more reviewsAmenities & Room:
bed was super comfortable too
5. Cozy cottage for two near the beach (from USD 274)
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.
Siesta Key, Florida, United States
1.07 km (0.7 mi) from Siesta Key Drum Circle
Top guest reviews
Host:
the owners are very attentive & kindLocation:
you can walk there easilygreat location for walking to the beach restaurants and shopswe had a great time the bikes were great location wonderfulwe love this place & dogs are welcome which is very important to usCleanliness:
everything is very clean and up to datethe bed is very comfortable and the linens are good quality and very cleanthe cottage was as described… clean comfy and had what we needed for a comfortable stayRead more reviewsAmenities & Room:
thanks for having nice beach chairs umbrella and comfortable patio furniturea nice living area with a little table to enjoy breakfast and do a little work
6. 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
7. Next to Siesta Key Public Beach (from USD 394)
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!
Siesta Key, Florida, United States
410 meters (0.3 ft) from Siesta Key Drum Circle
Top guest reviews
Host:
and the manager/host was wonderfulwe found virginia the proterty manager to be very helpful and responsivenessany questions we had were answered immediately by virginia - she is so friendly and helpfulvirginia was easy to communicate with and very accommodating as we ended up checking in earlier than expectedLocation:
great location close to beachlove the location and the area cute placewe enjoyed this location very muchsuper location for the beach and the villagevery good location nice pool had everything we neededCleanliness:
the unit was very cleanthe hide-a-way suite was very clean and comfortablethe hibiscus suite was very clean and nicely decoratedthe grounds felt manicured and the room was clean and invitingunit and complex is adorable and clean and well stocked with kitchen bath and beach necessitiesRead more reviewsAmenities & Room:
the bed was comfortable and all the other furniture was in great shapetherefore at night it is necessary to run the ceiling fan to cool the room and sleepthe pool area is a serene oasis
8. Beach views from all three floors! Royal Palm Suite (from USD 903)
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!
Siesta Key, Florida, United States
419 meters (0.3 ft) from Siesta Key Drum Circle
Top guest reviews
Host:
virginia (the manager was super helpful)i would definitely recommend this property owner was very helpful and always availableLocation:
we loved the locationit is the perfect locationbeautiful place walk to the beachwe also enjoyed walking to siesta key village several timesthis condo was the perfect place for a girlfriends weekendCleanliness:
super clean and quieteverything is updated and was clean when we arrivedthe property was extremely clean and everything worked perfectlyclean and updated space with a short walk to the beachbeautiful and clean easy 1/2 block walk to a beautiful beachRead more reviewsAmenities & Room:
the deck off the living room/kitchen is a perfect spot for morning coffee and evening drinksnew amenities in the kitchen and squeaky cleanthe master suite had huge closets and a very large bathroomtoo many great things to do outside to bother with watching tv
9. Siesta Key Beach – honeymoon suite with gulf views (from USD 461)
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.
Siesta Key, Florida, United States
419 meters (0.3 ft) from Siesta Key Drum Circle
Top guest reviews
Host:
management was very responsive and available too we loved our stay in the honeymoon suiteLocation:
perfect location thanks virginiathe suite was perfect and so close to the beachshort walk to the most beautiful beach we've been tovery roomy had everything we needed and super close to beach shops and dininghad an amazing time kid friendly clean amazing location and great priceCleanliness:
all it would have taken was some bleach to clean floorsRead more reviewsAmenities & Room:
it has the most comfortable furniture is quiet & clean
10. Just steps to the beach & 3 blocks to village
Last but most definitely not least is this condo vacation rental that sleeps from 4 to 6 guests. If you are really looking for a place to chill but is too tired of going to the beach? You can just enjoy the nice weather and relax in the best spot in this condo, which is the hammock with your furry friend. By the way, they are also a pet-friendly property. In this accommodation, you can have the best beach vacation beyond your expectation.
SARASOTA, FL, US
687 meters (0.5 ft) from Siesta Key Drum CircleTop guest reviews
Host:
the owner and the manager are very helpful and accommodatingpet friendly and well managedthe resort team was extremely nice and helpfulLocation:
the location was wonderful close to the beach and close to restaurant and shopping at siesta keythe location provides easy access to the beach as well as an easy walk to siesta villageit was really nice to be close to the village and the beachgreat stay very comfortable and walking distance to the beachCleanliness:
the room and property were exceptionally cleanRead more reviewsAmenities & Room:
the bed and the sleeper sofa were comfortableafternoons and evenings in the heated private pool were awesome as well as some middle-of-the-night swims :)
11. Reduced rate – stunning beach bungalow
This vacation rental is actually one of my many favorite accommodations in Siesta Key. The chic and trendy interior will surely catch your attention as you will truly feel the island vibe. The listing is stylish and is enough for 4 people to occupy and relax. It has nice location too as you can basically walk to most of the places of interest and is also near restaurants in the city. Make yourself at home and have the coziest stay you could ever have.
1.65 km (1.1 mi) from Siesta Key Drum CircleTop guest reviews
Host:
staff at the office were very friendly and helpfulthanks to adam and staff for making our stay relaxingthe check in staff was super friendly and we were greeted with a card and bottle of winewould definitely recommend this resort everyone very friendly and helpful during our stayLocation:
this property and location are perfectwe loved being so close to the beach and restaurantsthis was a great spot so close to restaurants beach and shops (like a couple min walk)very nice clean place with best location to walk to beach and into villagewhat a beautiful placeCleanliness:
it was very cleanthe unit was clean and nicely decoratedgreat spacious rental unit that was dog friendlythe beach area is clean and not very busysuper clean well appointed locationRead more reviewsAmenities & Room:
the kitchen is more than adequate with all the comforts of homewater cold this time of year and weather varies 60-70’s but overall comfortable
12. Reduced rate – tucked away bungalow
Another beach-themed vacation rental? Yes, that’s right and there’re many more! What more can I say? This listing says it all. Its cute and funky combination of colors is cooling and totally refreshing. Take advantage of their free 2 hour bike rental daily and have a nice ride along the beach.
1.65 km (1.1 mi) from Siesta Key Drum Circle
13. Price alert – sleeps 6
This nice resort property claims that if you book a stay with them, you can have the best of both worlds. Why not give it a try? With its many features and amenities, you can have a peaceful stay while enjoying the city of Siesta Key. Did I mention that this listing has the same owner from number 6? So you can also take advantage of the 2 hour bike rental, for free!
1.77 km (1.1 mi) from Siesta Key Drum CircleTop guest reviews
Host:
great front desk and housekeeping staffstaff was friendly and helpfulthe housekeeping staff was super friendly and we were the perfect distance to everythingLocation:
the property is in a great central locationperfect location two bedroom just the right sizeclose to the beach with a nice poolvery nice beautiful property in perfect locationCleanliness:
the property was clean & well keptour place was new and clean upon arrivalthe rooms could’ve been a little cleaner as wellthe rooms were clean and decorated nicely we enjoyed all the privacy of our own spaceRead more reviewsAmenities & Room:
only one bathroom but a delightful rental
14. Price alert – gorgeous pet-friendly resort studio
Still looking for more chic and stylish vacation rental for more photo opportunities? Try this listing that gives you another cooling and refreshing ambiance! This accommodation actually sleep up to 4 people but you might want to include your pretty little or big creature during your getaway. Four legged furry ones are welcome in this accommodation so they are not left out when you plan a vacation!
1.65 km (1.1 mi) from Siesta Key Drum CircleTop guest reviews
Host:
everyone was so friendlystaff were very friendly and willing to help youeveryone is very friendly and helpfulstaff was friendly and cheery - even though it was recently acquiredmy husband and i loved the charm location and friendliness of the staffLocation:
perfect location to the village and the beach awesome experience overallwe love this area but have never stayed so close to townour kids loved having the pool close by and the option to ride bikes when we wantedit was so well maintained and you can't beat the locationour family had a great time here very nice room in a perfect locationCleanliness:
our bedroom was very clean and comfortablethe bathroom was again clean and had a very spacious showerRead more reviewsAmenities & Room:
the room wasn't too noisy we were super happy with the location
15. Bright and airy townhouse with private beach access
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.
Siesta Key, Florida, United States
1.03 km (0.7 mi) from Siesta Key Drum Circle
Top guest reviews
Host:
the owner gave great recommendations on things to doshe is very nice and accommodatingvarinia was a great hosteveryone in the complex was so nice and friendlythe communication with the owner/host was greatLocation:
the location is perfectgreat location close to the beach easy walkthe location was fabulous with such easy access to the beachthe condo was short walk to the beach and close to restaurants and attractionseasy to book and varinia was very helpful great location on the beachRead more reviewsCleanliness:
the condo was very clean and updatedthe condo was clean & well keptthe property was very clean and equipped with everything you need for your vacationour condo was very clean and had easy access to the beachthe space is clean and fits the online description
16. Luxury villa Siesta Key
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!
Sarasota, Florida, United States
799 meters (0.5 ft) from Siesta Key Drum Circle
Top guest reviews
Host:
the local manager was super responsivethe property management was always friendly and available and quick to respond to any questions or concernsthe property manager was extremely helpful and niceproperty manager was responsive and great to work with as was the ownerwould recommend this property and definitely would stay with this host again did not want to leaveLocation:
perfect location for a beach getaway with familythe walk into the village is a little bit more of a walk but definitely doableRead more reviewsAmenities & Room:
pool and hot tub are great
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!
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