Holiday rentals in Siesta Key

5 out of 5 average rating, 111 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

5 out of 5 average rating, 188 reviews

Flat in Sarasota

Modern Luxury Apartment in a House Near Siesta

Large modern construction 950 square foot 1 bedroom apartment. Beautifully furnished, efficient apartment attached to the side of the main house. This unit has a private entrance with bright, modern interior and high ceilings. The apartment offers 1 King bed. The full bathroom has a large shower. A Washer and dryer located inside the apartment. Nestled on a quiet street with easy access to Siesta key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key. Great location!

4.9 out of 5 average rating, 116 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!

4.99 out of 5 average rating, 178 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!

4.93 out of 5 average rating, 108 reviews

Flat in Siesta Key

Siesta Premier Location - The 'Calm of Siesta'

My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

5 out of 5 average rating, 6 reviews

Home in Siesta Key

Coastal Elegance Pool Home in Sarasota

Welcome to coastal elegance in Sarasota! - Stunning 4-bed, 4-bath pool home on Palm Island - Recently renovated with modern open-concept layout - Gourmet kitchen with Italian Fulgor cooktop and marble island - Ground-floor master suite for privacy and luxury - Sun-filled flex room for various uses - Spacious outdoor area with newly renovated pool - Private dock access for boating enthusiasts - Just 2 blocks from Siesta Key Beach and 10.5 blocks from Siesta Village

5 out of 5 average rating, 39 reviews

Townhouse in Siesta Key

100 Steps to beach access & 5-min Village walk

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.

4.97 out of 5 average rating, 317 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!

Apartment in Longboat Key

5 out of 5 average rating, 8 reviews

Condo with View 4!

This sublime oceanfront condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

4.91 out of 5 average rating, 54 reviews

Cozy Top-Floor Stay on Siesta Key + Bikes

NO HURRICANE DAMAGE. We've been incredibly lucky that there was no damage to our condo! Welcome to this peaceful and centrally-located Siesta Key condo located in the Bay Oaks neighborhood. Walking distance to the beach, this condo includes everything you will need for your Siesta Key vacation! Included in your stay are 2 bikes with front baskets for getting around the Key. Siesta Key Free Trolley stop is right outside the entrance.

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.

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Popular amenities for Siesta Key holiday rentals

Kitchen

Wifi

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 stars2 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.

4.7 out of 5 average rating, 191 reviews

Vacation Condo on Siesta Key, FL

KyleRating, 5 stars3 weeks ago

Rae’s place was spotless and exactly as pictured in the listing. While the condo has a slightly dated feel, it was fully equipped with everything we needed for a comfortable stay. The hot shower was perfect after a day at the beach, and we especially enjoyed the new pool—such a great addition! Overall, a wonderful experience, and we’d definitely stay here again. 😊

5 out of 5 average rating, 4 reviews

Spacious 2BR 2nd floor Siesta Key condo - GBB 1274

AminaRating, 5 stars4 months ago

If you are looking for place look no further. It is close to everything and the place is beautiful inside and out. The host were great at keeping me informed via text. I can’t wait to come back in the future.

5 out of 5 average rating, 8 reviews

Apartment in Sarasota

Oceanfront - Hyatt Residences on Siesta Key Beach

ChristinaRating, 5 stars2 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.

5 out of 5 average rating, 7 reviews

Siesta Key Beach - Crescent Royale

JanineRating, 5 stars1 month ago

Very cute and comfortable condo. Excellent location to beach. We loved that there was a pavillion right across the street by the beach with very yummy food and drink selections....verry convienient!! Had our coffee and lunch there every day!! Jerry was very responsive!! For some reason there was only one pool towel in the cabinet. We were a party of 4. I texted Jerry about this and he responded very quickly! Within 1-2 hours, there was a bag of towels left in our condo by the staff! So appreciated! Beach umbrella was perfect as it was the only orange and white striped umbrella on the whole beach which made it verrrry easy to spot! :) Trolley stop basically right outside of the condo! Pillows on the bed were not comfortable at all....really need an upgrade there. Otherwise, everything was perfect!

Home in Siesta Key

5 out of 5 average rating, 3 reviews

Tropical Oasis house

RobertRating, 5 stars1 month ago

First and foremost, from our family to yours, thank you for such a wonderful spot for our family vacation. We've been going down to the Key for 30 years so it's all about accommodations. This spot is absolutely perfect. The pool alone is worth the trip. If anyone is looking for a solid home to spend a week, I cannot recommend this enough.

4.9 out of 5 average rating, 70 reviews

Flat in Siesta Key

Siesta Sand Dollar Cottage 1 Block Siesta Beach

MelanieRating, 5 stars1 week ago

We stayed here last year and loved it so much that we decided to rebook this year. The house was spotless, beautiful, and included everything we could possibly need. The location was spectacular; it was a short one block walk to the beach. The house is located in a mostly residential area so the particular area of the beach was quiet and peaceful. Additionally, the downtown village is only a 10-15 minute walk. Cannot recommend enough!