Some info has been automatically translated. Show original language

House holiday rentals in Siesta Key

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Siesta Key house rentals

House rentals with a pool

Guest favourite
Home in Sarasota
4.97 out of 5 average rating, 68 reviews

Sun-filled cottage with pool, walk to beach

MichaelRating, 5 stars2 weeks ago
We loved our recent stay here! We had a bit of a challenge with lots of rainy weather so having a BEAUTIFUL backyard with synthetic grass and an amazing pool SAVED THE DAY(S). We ran outside with every break in the weather and the kids stayed as happy as can be. The home not only looked clean, but FELT clean and the decor was tasteful and didn’t feel overly beach kitschy- as we’ve run into before. Hoping to be back next year!
Guest favourite
Home in Siesta Key
4.77 out of 5 average rating, 512 reviews

Beachfront Getaway in Siesta Key

AdairRating, 5 stars2 weeks ago
Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!
Guest favourite
Home in Venice
4.95 out of 5 average rating, 107 reviews

Spacious 2 Bedroom Home | Near Beach | Heated Pool

SarahRating, 5 stars1 day ago
Melissa's listing was very nice and comfortable. The beds were comfortable and the ceiling fans worked great. The bathrooms were clean and the showers had good water pressure. There was lots to do in Venice and a drive to Sarasota was at most an hour. It was also nice that beach items were supplied, such as chairs, umbrella, coolers, etc. The house was also in a quiet neighborhood and we felt safe at all times. I would definitely recommend to others!
Guest favourite
Home in Sarasota
4.94 out of 5 average rating, 152 reviews

La Hacienda / heated pool, hot tub, 6 mi to beach

CarlynRating, 5 stars3 weeks ago
Fantastic Airbnb! Seaglass Management and Joy are great to work with. Very responsive! Great location, very safe, amazing pool and jacuzzi, close to downtown, restaurants and the Legacy bike trail. Will definitely book again in the near future.
Top Guest favourite
Home in Siesta Key
5 out of 5 average rating, 144 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

ZacharyRating, 5 stars1 month ago
Marko’s family home was beautiful, charming, and spotlessly clean. The home is perfectly located, walkable to beautiful beaches and great restaurants and shops, including the market. Marko was extremely hospitable, ensured we were all set and gave wonderful recommendations. We loved this place and will be back again next year. Thank you!
Guest favourite
Home in Sarasota
4.92 out of 5 average rating, 92 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

StephanieRating, 5 stars4 days ago
We had a great stay! The house was exactly like the photos and was very fresh and clean! Instantly felt like a tropical vacation when we walked in. Check in was easy and Michael was awesome with his quick responses, flexible early check in and local recommendations! We went to Walt’s fish market as he suggested and it was so worth it! Amazing seafood! Definitely looking forward to booking this airbnb again when we visit! The house is in a great area so close to everything! Highly recommend!
Guest favourite
Home in Sarasota
4.98 out of 5 average rating, 45 reviews

Casa Blanca Ranch Home near Siesta Key Beach

JulioRating, 5 stars3 weeks ago
Casablanca exceeded my expectations. The house is much larger than it looks in the photos, with a large and well-equipped kitchen. The house is very cozy and comfortable, and I can't forget to mention how clean the house is. Matthew was super nice and responded to my messages promptly. I have no complaints about the house, and I would definitely rent it again. The outdoor area is very nice, and we had great family moments there, enjoying the pool and having a barbecue. The neighborhood is very peaceful and quiet. The garage has everything you need for a peaceful day at the beach, from chairs and coolers, to even tents if necessary. The location is very good, with stores and supermarkets very close by. It took us about 12-15 minutes to get to Siesta Key. Anyway, I definitely recommend the house!
Superhost
Home in Siesta Key
5 out of 5 average rating, 3 reviews

Rustic Sands - 650

Leon Rating, 5 stars11 months ago
Our time at this Airbnb in Siesta Key was amazing! The house was super clean and had an awesome kitchen with everything you could think of, plus more. Great appliances, tons of towels, dishes, some games, TVs with premium channels and more! Outside was just as great. The pool area was covered with mosquito netting, so we could relax without bugs bothering us. The pool was our favorite spot! super clean, and the outdoor BBQ grill was great! The only thing was the master bedroom bed was a bit small and not the most comfortable for us (queen size), but everything else was so good. The neighborhood was really quiet, location was 4 minute drive from the beach. Overall, this Airbnb was one of the best places we've stayed. I would 100% recommend it and would come back! it looks better in real life than the photos.

Weekly house rentals

Guest favourite
Home in Sarasota
5 out of 5 average rating, 27 reviews

Stunning Home, Heated Pool and Boat Dock

Joshua ThomasRating, 5 stars1 week ago
We had a wonderful experience! The bay was beautiful and we got to see manatees! Highly recommended!
Top Guest favourite
Home in Sarasota
4.99 out of 5 average rating, 69 reviews

Luxury Pet friendly home, 2.7miles to Siesta Key!

CarenRating, 5 stars6 days ago
We had a wonderful stay at this property. We were in town for our son's sporting event for several days. It was exactly as described and more. It was clean and comfortable and there were so many "extras" that we do not usually experience in other rental properties. The kitchen was fully stocked with utensils, cooking supples, spices, coffee, and more (better than any rental we've stayed in). There is not one negative thing I can say about this place or the host. Honorata was extremely responsive and helpful and allowed us to check in early, which we greatly appreciated as we needed to drop our luggage and go to an event. The location was great, a short drive to the beach, stores, etc. and the neighborhood was quiet and felt safe. We would highly recommend this property and hope to stay there again next time we are in the area. Thank you Honorata and Conrad for a lovely stay!
Top Guest favourite
Home in Sarasota
4.98 out of 5 average rating, 51 reviews

Charming Home in Sarasota-8min from Siesta Key

KhloeyRating, 5 stars2 weeks ago
The hosts were very responsive and very helpful. Their home was spotless. The pool with the enclosure allowed you all the sunshine you could ask for without the bugs! The interior is very spacious and great for hosting dinner. With the turf back yard it’s the perfect hangout for adults and children! The hosts are very thoughtful with items available for the perfect beach day (beach wagon, chairs, a cooler, and lots of fun items for children! We will definitely be visiting again!
Guest favourite
Home in Sarasota
4.97 out of 5 average rating, 61 reviews

Stunning New 3 bed 3 bath pool home by Siesta Key!

IngridRating, 5 stars4 weeks ago
Adam’s place was just what we needed for our family vacation! Super close to the beach, which made it easy to pop over for a few hours of fun with the kids, then head back for naps and chill time by the pool. It was the perfect mix of fun for the little ones and relaxation for us. We couldn’t have asked for a better spot!
Guest favourite
Home in Sarasota
4.96 out of 5 average rating, 98 reviews

Sea La Vie On Brink- cheerful 3/2 w/ shuffleboard

SherryRating, 5 stars2 months ago
We enjoyed staying here and will be back.
Top Guest favourite
Home in Sarasota
4.99 out of 5 average rating, 80 reviews

Cottage w/Fire Pit Near Siesta!

AmberRating, 5 stars2 weeks ago
This house was beyond what we expected and we look forward to renting it again for our next Siesta Key trip. Betsy was outstanding and such a wonderful host.
Guest favourite
Home in Bradenton
4.95 out of 5 average rating, 43 reviews

Stay & Play - 4 min from IMG

AngelinaRating, 5 stars2 days ago
I had a great experience staying at this Airbnb! The place was exactly as described clean, comfortable, and had everything we needed for a smooth stay. The host was amazing very friendly, responsive, and easy to communicate with.I would definitely stay here again and highly recommend it to anyone looking for a hassle free and enjoyable stay!
Top Guest favourite
Home in Sarasota
5 out of 5 average rating, 15 reviews

1 Bedroom Cottage 7 Min to Siesta Beach

MartinRating, 5 stars2 weeks ago
Great place to stay !! Love the location, only 8 minutes to Siesta Beach!! Everything was close by, easy access to two of the main thoroughfares, Tamiami Trail and Clark. Strait shot to 75 , too. Loved the gas grill and patio furniture. Had a few little visitors out there, a couple of Geikos running around keeping me company while I was grilling. Very clean and newly redone throughout. Beautiful place, highly recommend it !!!

Private house rentals

Top Guest favourite
Home in Sarasota
5 out of 5 average rating, 17 reviews

Lovely Beach Bungalow

AlyRating, 5 stars1 day ago
Olga’s place is such a gem! We had a wonderful week long stay - we felt right at home the moment we stepped inside! Olga was so sweet and always made sure we had what we needed. The pool was an added bonus, it felt like we had a private oasis to hang out at after we went to the beach. The house was impeccably clean and stocked with everything you could possible need for a comfortable stay. The AC was lovely and the beds were so comfy, everything about this airbnb exceeded our expectations. We didn’t want to leave, but already can’t wait to come back one day. We highly recommend Olga’s place 😊
Guest favourite
Home in Sarasota
5 out of 5 average rating, 5 reviews

Paradise on Prospect w/ Htd Saltwater Pool

NatalieRating, 5 stars3 months ago
This is the nicest vacation rental. The details are spot on. It is well appointed with quality products. PMI Is very responsive. Love the location and proximity to Ed Smith, Downtown Sarasota and more. We look forward to returning.
Guest favourite
Home in Englewood
4.88 out of 5 average rating, 32 reviews

Suite Sun

BridgetRating, 5 stars1 week ago
Our stay at Ryan’s place was perfect. It felt private even though it’s in a neighborhood. The location was great for our beach and shopping trips. There are several amazing local restaurants within a few miles. We’ll definitely be back!
Top Guest favourite
Home in Sarasota
5 out of 5 average rating, 17 reviews

Ground floor home 2BD2BA garage Pool Private beach

NoraRating, 5 stars4 weeks ago
We had a fabulous stay! The location is perfect. The condo was spotless and nicely decorated. We had absolutely everything we needed. The private beach was clean and not crowded. Chairs were readily available. The location is great. There was an unexpected issue when we first arrived, but Amy was incredibly responsive and supportive, checking in regularly to make sure we were okay and comfortable. Her excellent communication and customer service was exceptional. Once everything was settled, we were able to fully enjoy the space and the beautiful surroundings. Can't wait to go back. We would definitely recommend booking this property.
Top Guest favourite
Home in Siesta Key
5 out of 5 average rating, 14 reviews

The Shore House Private Dock Hot Tub

BrianRating, 5 stars5 days ago
Greta stay - perfectly decorated and in a greta location.
Guest favourite
Home in Siesta Key
5 out of 5 average rating, 31 reviews

Paradise In Siesta!

EmmaRating, 5 stars3 weeks ago
We had a great stay here! Walking distance (10 minutes) to the beach and cute neighborhood. Great place!
Guest favourite
Home in Sarasota
4.93 out of 5 average rating, 88 reviews

St Armand's Mid-Century Oasis

PatriciaRating, 5 stars1 week ago
Had such an amazing stay at James home. Home was beautiful and at great location the pool was definitely a plus. Home was just as expected from description provided. I really loved the location of home as everything was walkable distance to near by shops, restaurants, bars, and beach. Would definitely stay again .
Guest favourite
Home in Sarasota
5 out of 5 average rating, 15 reviews

NEW hideaway, Saltwater Pool&Spa, 10min to Siesta

SandraRating, 5 stars1 month ago
I will definitely go back and stay here again when in Sarasota. The new beautiful modern pool and hot tub area is amazing was so tranquil and well thought out with high end lounging/seating for 10+. I spent most of my free hours around the pool area when at the house. WIFI was great when needing to work. The location was an easy drive to the local restaurants and quaint downtown area 5-10 min., to the closer beaches 15 -30 min., was bicycle/walkable for me (I am 65 y/o). I was in town for a conference and also saw alot of people on nearby small/clean little open air trolley-like buses getting around downtown (might want to check those out). I felt safe and walked/explored to the downtown hotel area (~ 40 min.). So close to the convenient Sarasota/Bradenton airport (~20 )! The hosts were so responsive and genuinely caring, they anticipated my needs before I asked by offering suggestions and options, so worth the stay! Thank you to the hosts!

Quick stats about house rentals in Siesta Key

  • Total rentals

    420 properties

  • Total number of reviews

    6.7K reviews

  • Family-friendly rentals

    390 properties are a good fit for families

  • Pet-friendly rentals

    200 properties allow pets

  • Rentals with a pool

    290 properties have a pool

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Siesta Key
  6. House rentals