Holiday houses in Siesta Key

5 out of 5 average rating, 112 reviews

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach Accessories • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises

4.92 out of 5 average rating, 515 reviews

Guesthouse in Sarasota

La Casetta: "the little house" near to the beaches

La Casetta means, in Italian, little house. Set in a private, peaceful, mature Florida tropical garden, a real hideaway. I am proud of the cleanliness of our property, however in this new reality that we live in, we do carry out enhanced cleaning and sanitizing between guests. We also practice social distancing, insofar as guests have their own part of our luscious back garden as well as your own entrance. La Casetta has 1 queen sized bed, bathroom & kitchenette. Wifi & Netflix available.

4.9 out of 5 average rating, 117 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

4.93 out of 5 average rating, 111 reviews

NO Stairs, beachfront & short walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

4.99 out of 5 average rating, 179 reviews

Guest suite in Sarasota

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

4.97 out of 5 average rating, 32 reviews

Bungalow in Siesta Key

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard & a dock on Heron Lagoon. A resort with something for everyone. The Mermaid Bungalow's airy one bedroom space; has an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed, bathroom and a veranda, you'll feel at home. The Coquina is fully stocked with linens, care essentials, plus eating & cooking utensils. An additional single-roll-away-bed allows accommodations for three guests.

Guest suite in Siesta Key

4.92 out of 5 average rating, 173 reviews

Cozy Studio - 5 min walk to #1 Siesta Key Beach!

Recently renovated and updated! Adorable studio just steps from Siesta Key Village, and a 5 minute walk to the beach. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**

Superhost

Home in Siesta Key

5 out of 5 average rating, 4 reviews

Designer Home| Sleeps 10| Walk to Beach & Village|

Steps from Siesta Key Beach, this beautifully renovated 3-bedroom, 3.5-bath home offers sophisticated coastal-inspired decor. The master suite has a private screened balcony overlooking the pool with an egg chair swing. A screened patio includes bar seating, a dining area, and a cozy lounge. The first-floor mudroom has a shower for easy beach cleanup. With its classic beach cottage feel and modern amenities, this home is the perfect coastal retreat. Book now!

4.97 out of 5 average rating, 318 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

5 out of 5 average rating, 335 reviews

Home in Sarasota

Stunning Luxe Casita- Gateway to Siesta Beach

Newly built and completed in 2019; this guest house is just a few minutes walk to one of the world's best beaches, Siesta Key. Your own private drive to this elegant secluded enclave is close to shopping, restaurants and all the fun Sarasota and Siesta Key offer. Tall ceilings, double pane windows, extraordinary insulation, beautiful finishes and furnishing details make this an unusually quiet and comfortable refuge.

4.94 out of 5 average rating, 106 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

4.89 out of 5 average rating, 283 reviews

Apartment in Sarasota

VILLA 3 · Pool view. Walk to beach. Daily rentals

Villa 3 is newly renovated Everything has been remolded and upgraded Featuring 1 bedroom, 1 bathroom,With 2 person shower with beach pebble floor Separate living room, With Large SMART TV A/C, stainless steel fridge, freezer, toaster, free wifi 2 minutes walk from your door to the beach access #13 Shared swimming pool at your door Perfect for couples No smoking No pets Great Location Good Value

Holiday rentals for every style

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Quaint homes, peaceful surroundings

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Popular amenities for Siesta Key holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Siesta Key

5 out of 5 average rating, 17 reviews

Home in Sarasota

Ground floor home 2BD2BA garage Pool Private beach

NoraRating, 5 stars3 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.

4.92 out of 5 average rating, 12 reviews

Home in Sarasota

Coastal Calm - 3BD/2BA Heated Pool Near Beaches

TeairaRating, 5 stars2 weeks ago

Beautiful home and location. Felt like home, spacious living, lovely neighbors and close to the beach.

Superhost

4.91 out of 5 average rating, 44 reviews

Dreamview Beachfront Romantic/Pet Friendly Getaway

RobinRating, 5 stars3 months ago

Fantastic location on quieter area of beach but still walkable to the Village restaurants. Comfortable bed, huge shower. Loved our stay!

5 out of 5 average rating, 5 reviews

Townhouse in Siesta Key

Villa Marina (1 Block from beach with heated pool)

DonRating, 5 stars3 weeks ago

Great place with a great host to match. Very nice place and close to everything. Private shared pool was great. Gabriel was a great host and helpful as always.

4.99 out of 5 average rating, 78 reviews

Home in Siesta Key

Relax in a Private Tropical Retreat on Siesta Key!

SteveRating, 5 stars6 days ago

myself with my Partner Paula, daughter Sammy and her boyfriend Tom stayed at Jonathan's wonderful house for 2 weeks, starting May 25th 2025. We were all delighted with the house and fully equipped with all our needs. We made use of the communal pool and found those that lived in the community very helpful and friendly. We made use of the Breeze bus that was great for going to the village. I made contact with Jonathan a few times regarding minor things and he responded very quickly.

5 out of 5 average rating, 20 reviews

Home in Siesta Key

Newly Remodeled Beach House on Siesta

ShannonRating, 5 stars1 month ago

My family and I loved our stay at Danielle’s. The house is in a truly beautiful setting right on the canal — we spent lots of time fishing! We easily walked to the beach and into town every day, about 15 min. Danielle provided us with all the beach/kid/baby supplies we needed for our family, which was so thoughtful. All supplies like soap, shampoo, detergent, toilet paper, etc were also provided, which was much appreciated for weary travelers. Highly recommend!

5 out of 5 average rating, 8 reviews

Condo in Sarasota

Oceanfront - Hyatt Residences on Siesta Key Beach

ChristinaRating, 5 stars3 weeks ago

Fabulous condo! Absolutely beautiful, exactly as pictured if not better! Stunning views of the gulf from the balcony, we loved eating breakfast out there. Amazing amenities, including the beach chairs and umbrellas. The rental owner was very helpful, was great about checking in with us. Check in and check out process was very easy. We would absolutely love to stay here again.