Blessed with the beauty of the Gulf of Mexico, Siesta Key is a slice of heaven on Earth and a fabulous destination for nature lovers, sun-seekers, and watersports enthusiasts. This Sunshine State barrier island is home to Siesta Key Beach - a family-friendly public beach with sports facilities and a playground that kids love. The Crescent Beach boasts magical sunset views that you can not miss seeing while holidaying here. At Turtle Beach, you can enjoy picnics with your loved ones and watch nesting turtles. With a destination as action-packed as Siesta Key, it is no surprise that visitors never want to leave - or stay longer than planned. If you’re planning a long-term holiday here, be sure to book the right accommodation for you. Browse this list of the best monthly rentals in Siesta Key, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on September 01, 2025.
1. Casa Berano (from USD 3734)
Attracting meticulous vacationers, this Airbnb is tastefully curated with bright and sunny interiors and a vibrant interior design, echoing Mediterranean ambiance. Here, you can enjoy standard home fittings, such as an equipped kitchen, a living room with a Smart TV, and spotless baths. You’ll have a patio, which is the perfect spot for morning coffee, and a swimming pool, ideal for any time of the day.
Casa Berano strictly allows six guests only. Up to two dogs can be accommodated. If you’re interested in this property, note that it has a 7-night minimum stay policy, and month-long stays are rewarded with a discount.
Siesta Key, Florida, United StatesSuperhost
Accommodates: 6
Top guest reviews
Host:
debi and cage are wonderful hosts and readily availablethe hosts cage and debi take their roles as super hosts seriouslywonderful space and amazing hoststhe owners were responsive to any questions about the house or areacage & debi are very responsive and wonderful hostsLocation:
location to everything was greatamazing house in a great locationthis a great location and great valuegreat location just minutes from the beach and villagelocation is great only minutes from siesta beach and downtownCleanliness:
house was super cleanthe property was also clean upon our arrivalthe house was sparkling clean and more than comfortablethe house was very clean and well set up for our familywell stocked clean and the pool was a plusRead more reviewsAmenities & Room:
it is very comfortable and has all the amenities needed for a perfect vacationamazing home such an incredible location with incredible amenities the pool and grill outside were excellent to havefrom little touches such as hand sanitizer and the most comfortable bed everthe screened lanai and pool are perfect as was the grillthe pool is a nice size (deepest being about 5ft) with beautiful tropical foliage canopying it
2. Sea Club II Garden House (from USD 1568)
This Airbnb is a freshly renovated beach bungalow showcasing rustic flooring, modern decor, and stainless-steel appliances. When some of you are preparing meals in the well-equipped kitchen, the rest of the pack can watch movies in the living room or browse the web to their hearts’ content. A washer and a dryer are available in this air-conditioned dwelling for added convenience, and you can find a bathtub here, too. In your leisure time, you can enjoy fresh air on your private deck or indulge in refreshing laps in the community pool.
This accommodation can be booked for as short as a three-night stay. Those on an extended holiday can enjoy monthly discounts.
Siesta Key, Florida, United StatesAccommodates: 8
Top guest reviews
Host:
the home was spectacular and the hosts were wonderfulhost was very helpful and got back to us with any questions we had very prompteveryone we met was friendlyhost responded within and hour or so to questions which is nicethe list of grocery stores with addresses was very helpful tooLocation:
great condo in a good locationthe location was greatthe location is greatthe location was fabulousgreat place and location for family vacationCleanliness:
clean and spacious condovery clean and beautifully furnishedthe house was very clean and just as describedeverything was very clean and the beds were super comfortableit was very clean and everything we needed was there and then someRead more reviewsAmenities & Room:
loved the living room with wrap around couchthe pool was great and not crowded and the communal grills were brand new and nicethe space is updated stylish and comfortablewe only touched one of the beds the master bedroom and it was firm and comfortable
3. Tourist-friendly abode with a pool and a hot tub (from USD 472)
Suitable for long-term stays, this property has a minimum 14-night stay policy. It can accommodate month-long stays, as well. The property boasts a fully furnished interior design and a tourist-friendly location, steps from the white-sand Siesta Key public beach. An outdoor pool is available on the premises, should you prefer to stay at home for the day. There’s also alfresco dining and barbecue equipment for your cookouts. A hot tub is a bonus.
Sarasota, Florida, United States
Top guest reviews
Location:
i loved the location of this house it’s great proximity to the beachbeautiful property close to the beachbeautiful siesta beach is a five minute walk awaywe had a wonderful time at this locationRead more reviewsCleanliness:
the house was clean and very comfortable in a quiet neighborhoodthe house is cozy clean and comfortable
4. Fully furnished two-bedroom abode (from USD 270)
Are you seeking comfortable and convenient accommodation in Siesta Key that can host you for a month? Check out this two-bedroom apartment that can accommodate weekly and long-term stays. Discounts are afforded to month-long guests.
Since it is fully furnished, you can expect a kitchen, laundry appliances, and WiFi. A private pool and a hot tub are delightful additions. In the mood for a saltwater soak? The beach can be reached on foot in eight minutes.
Sarasota, Florida, United States
Top guest reviews
Host:
this is an amazing property with a great hostthe hosts were nice and very easy to work withthe house & hosts were great the house is everything i expected and exactly as advertisedLocation:
the location is ok as well about a half mile walk to the villagethe property is in a good location closeto beaches restaurants and the siesta villageRead more reviewsCleanliness:
very clean comfortable and neat facilityrental was very roomy and cleanthe place is clean conveniently located and my kids love the private pool
5. Pet-friendly dwelling with WiFi (from USD 274)
Long-term holidayers will love this tropical vacation rental, offering a discount for month-long bookings. Apart from the generous price slash, the location, steps from Siesta Key Beach, thrills patrons. The fully furnished concept is worth appreciating, as well. You can whip up your favorite meals daily, access the web, and bring up to two beloved little pooches. Do note that a pet fee will apply.
The best part? A heated swimming pool tucked in tropical foliage awaits in the backyard.
Siesta Key, Florida, United States
Top guest reviews
Host:
met the owners briefly friendly as expected from our mail communicationmet the owners briefly friendly as expected from our mail communicationthe house was well-stocked well-appointed and owners very thoughtful about all the detailsLocation:
the house is in the most perfect location near the beach and the villageRead more reviewsCleanliness:
quiet clean and just perfect for our needsquiet clean and just perfect for our needsthe property was very clean and very well equipped we didn't want for anything
6. Freshly remodeled villa with pool access (from USD 237)
This posh villa is suitable for beach-goers, as it is within arm’s reach of Siesta Key. It also offers a freeform pool, where you can take a plunge as soon as you exit your lovely little abode. Suitable for a pair of travelers, this VRBO is equipped with a king-size bed, an open kitchen, and a seating area with a wide-screen TV. Since the internet is accessible here, you can enjoy a work-from-home setup.
Note that this accommodation has a varying minimum stay policy, but month-long stays are welcome, and discounts are available.
Sarasota, Florida, United States
Top guest reviews
Location:
it was a cute little place located in a nice spot with a short walk to the beachgreat condo in a fantastic location will be back againthe short drive to shops and restaurants made this a great locationgreat location can walk to the beach and also restaurants and barswe had easy access to the public beach with a very short walkCleanliness:
the property was clean and super cuteour rental was clean tidy and had everything we neededa little off the beaten path but nice easy beach access clean people were niceRead more reviewsAmenities & Room:
the air conditioner worked a little too well but that’s a good thingsmall pool was great as an alternative to the beach
7. Modern apartment with sea views
This apartment’s top-selling factor is its location, a stone’s throw away from Siesta Key Beach. Its well-curated modern design is a good selling point, too. Wooden floors, white walls, and expansive windows make the look of this cozy retreat. For convenience, a kitchen, a dining area with a view, and WiFi are at your service. Access to a gym and a heated outdoor pool are included in the rate.
Whether you are staying for a week or a month, you are welcome to avail yourself of this superb rental. Month-long stays can enjoy discounts.
Siesta Key, Florida, United StatesAccommodates: 4
Top guest reviews
Host:
the owner was a pleasure to deal with from the start and easy to communicate withcarlos is a great host sal property manager was great as well hope to return soonagain not the owner's faulti can’t say enough good things about this condo the owner and the property managersonly a few minutes walk across the street sal the property manager was very friendly and accommodatingLocation:
perfect location near the beachgreat location that need some tlcexcellent location right across from the beach—walking distance to everythingeasy walk to the beachgreat place with great location and nice poolCleanliness:
it was clean and cozythe pool is very cleanoverall condo was clean cute and comfortable for our family of 4Read more reviewsAmenities & Room:
furniture and beds comfortablethe pool is very nice with plenty of chairs loungers and tables with umbrellas
8. Pin Oaks Cottage
A tourist-friendly abode with an Old Florida vibe, Pink Oaks Cottage is nestled in Sea Club 2, within proximity to Siesta Key Beach and Crescent Beach. Shops and dining spots are easily reachable on foot from this accommodation, making it loved by past guests even more. In addition to a kitchen, air-conditioning, and laundry facilities, the humble abode provides WiFi - a sure hit with most people staying for a month or more.
This rental can accommodate both short-term stays and month-long holidays.
Siesta Key, Florida, United States
Top guest reviews
Host:
property manager rae is very responsive to any questions or requestsLocation:
cute little cottage in a nice location not far from the beachthere also are free shuttle buseslocation by the water and pool is greatold florida charm :)cozy cottage close to main beachCleanliness:
house was very clean as well as the groundsRead more reviewsAmenities & Room:
pool area was great with beautiful views of the intercoastal waterwayvery comfortable unit in an exceptional setting
9. Three-story dwelling with a modern kitchen
This superb accommodation is a wise choice for families, as it can accommodate up to eight guests, and a small, well-behaved fur baby can be allowed. The three-story property is modernly furnished with stainless-steel kitchen facilities, air-conditioning, and heaps of natural light. Business travelers can enjoy free WiFi, and a private pool and a hot tub are available for lazing out.
This family-friendly accommodation imposes a 15-night minimum stay. Month-long stays can also be accommodated - with discounts.
Sarasota, Florida, United States
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
10. Superb apartment with alfresco dining
For a minimum of seven nights’ stay, you can take advantage of this thoroughly sanitized property. It also seasonally welcomes month-long stays, in case you’re on a long-term business trip in Siesta Key. This beautiful abode showcases an open-plan layout with an elegant kitchen, a cozy living space with a Smart TV, and a six-seater dining set. There’s alfresco dining with a gas grill for your barbecues, as well.
Guests of the apartment can access the community clubhouse and the pool. The beach can be reached in four minutes on foot.
Sarasota, Florida, United States
Top guest reviews
Host:
house was very clean owner was able to answer questions quickly and was very helpfulLocation:
the location is great so that the walk to the beach was only about 5 minwe loved our stay here excellent location close to the beach and right next to the pool and laundrydidn’t care much for the beach within walking distance but loved turtle beachCleanliness:
pool was clean and very accessible condo was well kept and spaciousspacious and clean in a well cared for communitythe unit was very spacious and comfortablevery clean excellent patio and seatingRead more reviewsAmenities & Room:
beautifully renovated kitchen that was fully stocked
Have a fun-filled holiday in Siesta Key
Siesta Key is a gorgeous and fun-filled destination that deserves a month-long visit. It is packed with exciting recreational areas, from natural ones to man-made ones. To make your long-term stay comfortable, be sure to choose accommodation from this list of the best monthly rentals in Siesta Key, Florida.
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