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Siesta Key vacation rentals

Vacation rentals in Siesta Key by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.

Siesta Key attracts sun-seekers to Crescent Beach, the snorkel-friendly waters of Point of Rocks, and Turtle Beach Park's quieter shores. Known for its uniquely powdery white sand, Siesta Key Beach draws visitors for swimming, sunbathing, and weekend drum circles. Houfy allows you to book Siesta Key properties directly from owners, maximizing your vacation budget. Explore options from beachfront condos to charming cottages near the Village's dining and nightlife. With its pleasant Gulf breezes, Siesta Key remains a popular retreat year-round, although summer offers notably lower accommodation rates.

Top-Rated Vacation Homes in Siesta Key

Browse the highest rated vacation properties in Siesta Key.

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bd·1 ba
5· 2

$2,384.30 USD total for 7 nights

Oct 24 – 31, 2026

Beautiful Home & Hospitality
It was our first time at Siesta Key and Mark and Pam were wonderful with providing us with information about the area and were always quick to respond whenever I had any questions. The house is beautiful, cozy, and bright! It's close to many beaches and delicious restaurants. The house has anything and everything you could ever want in a rental - especially as guests who fly in and try to limit what we bring with us, they provided us with all the essentials and more- beach towels, beach chairs, umbrella, beach bags, shampoo/conditioner/body wash, indoor/outdoor games, and anything you'd ever need in a kitchen. The beds and furniture are all so comfortable as well. We loved having a washer and dryer while on vacation too. They literally have thought of EVERYTHING to make your stay cozy, comfortable, and enjoyable. I cannot wait to go back and explore the Siesta Key area again - everything was perfect!
Kalee · Stay June 2026

Blanca Cottage| Private 2BR Pool Home Near Siesta

2 bd·2 ba
5· 2
A Beautiful, Comfortable Stay with a Wonderful Host
We had a wonderful stay at Humaira’s home. The house was beautiful, clean, comfortable, and had everything we needed to enjoy our vacation. Humaira was a very kind, helpful, and responsive host, always making sure we were comfortable and had everything we needed. We truly enjoyed our stay and would definitely recommend her home to anyone looking for a relaxing and enjoyable place to stay. We would be happy to come back again in the future!
Lisandra Dominguez · Stay August 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key

5 bd·4 ba
5· 2
Everything Was Perfect!
Hi Humaira. I'm so sorry I couldn’t leave a review of our stay at your place. I missed the airbnb dead line for leaving a review. We had a wonderful stay at your house. Everything was perfect. Your house is beautiful. I will recommend it to all my family and friends going to that area for sure.Thanks a million
Radouan R · Stay July 2026

Siesta Key Home | Heated Pool, Theater & Arcade

4 bd·3 ba
5· 36
What a beautiful home! Our two families came together for the trip and had an amazing stay. There was plenty of space for everyone to spread out and enjoy some privacy, and the kids had a blast with the pool, game room, and theater room. The kitchen was perfect, the beds were comfortable, and the entire house was exceptionally clean and well kept. We also really appreciated having a beach sand wagon- beach chairs, umbrellas, and sand toys available to borrow—it made our beach days so much easier. The outdoor shower was another great bonus! The driveway and surrounding property were spacious, and the nearby downtown areas were only a few minutes away by car. The host was extremely responsive and shared lots of helpful suggestions and advice throughout our stay. We would absolutely stay here again!
A. F. · Stay July 2026

Village Canal home short walk to Beach with pool

3 bd·2 ba
5· 26

$14,950.00 USD total for 28 nights

Apr 15 – May 13, 2027

I don’t feel like 5 stars is high enough. We had an AMAZING stay! The house was beautiful and loaded with anything and everything you can imagine. It was very clean and accommodating. Perfect location! Walking distance to the beach and Siesta Village with lots of shops and restaurants. The kids had a blast in the pool every day! The beach is fabulous of course but it’s a lot of work to load up all the beach stuff so when you are just wanting to cool off or play in the water, the pool is such a great feature. We enjoyed the spa every morning and evening as well. One of my favorite activities was kayaking all over the canal. So peaceful and fun and right out the back door. I also tried out the paddle board which was a tad more challenging but I’m happy to report I did not fall off! The guys had a great time fishing in the canal while the kids played in the pool. We brought poles but there are also some in the garage that were available to use. My son in law caught a catfish! The courtyard is spacious and beautiful, private and safe for little ones to run around while you relax, grill out and enjoy your favorite cocktails. The house itself was so comfortable. Plenty of seating, TVs in every room, and the kitchen is full of great cookware and utensils. Some I have never seen or even knew how to use 🤣. There is a lot of counter space as well. There is a beach cart, an umbrella and 8 chairs you may use at the beach so no need to buy and bring any. We are already looking at our schedules to see when we can come back. If you are going to siesta key, this is the place to stay! You won’t regret it. It was an expensive stay, but I feel like it was worth every cent with all the extras included. I could go on and on. We really loved it!
K. · Stay June 2021

Palm View at Siesta Dunes

2 bd·2 ba
5· 15

$2,580.08 USD total for 7 nights

Sep 23 – 30, 2026

Our stay at the Villa at Siesta Dunes exceeded our expectations.
The Villa was everything as shown in the listing. While it didn't have a direct ocean view, it was only a couple minutes walk to be down on the surf. All the amenities of the grounds and the Villa itself provided for a great vacation experience. Everything is updated and has a comfortable feel. Plus the Villa is nicely insulated from outside noise if you want to sleep in!
J. · Stay May 2026

Recommended Homes in Siesta Key

Handpicked properties we think you'll love in Siesta Key.

#1 Siesta Key Beach Glass House w/supplies

2 bd·2 ba
4.64· 58

$2,062.25 USD total for 7 nights

Sep 26 – Oct 3, 2026

Beach, Bay, Food, Fun - 2BD/2BA

2 bd·2 ba
4.67· 9

$1,488.48 USD total for 5 nights

Oct 7 – 12, 2026

The Sapphire Escape

1 bd·1 ba

$2,053.91 USD total for 14 nights

Oct 21 – Nov 4, 2026

The Indigo Escape

2 bd·2 ba

Sandy's Siesta Key Condo

2 bd· ba

Casa mar - Unit 74

1 bd·1 ba

$873.20 USD total for 3 nights

Sep 23 – 26, 2026

$941.60 USD total for 3 nights

Sep 23 – 26, 2026

Why visit Siesta Key

Discover what makes Siesta Key a perfect vacation rental destination.

World-Class Beaches

Home to Siesta Beach, ranked #1 in the U.S.

Siesta Beach's powdery quartz sand is a must-visit, located just 2 miles from the island's heart. Join the Sunday evening drum circle, a local tradition.

Water Sports Galore

Perfect for kayaking and paddleboarding.

Rent kayaks from Siesta Key Paddleboards, only 1.5 miles from Crescent Beach. Explore the mangrove tunnels and spot local wildlife.

Family-Friendly Fun

Enjoy activities for all ages.

Take the kids to Siesta Key Village for ice cream at Big Olaf Creamery, located just 3 miles from the south tip.

Vibrant Nightlife Scene

Bars and live music just steps away.

Visit Siesta Key Oyster Bar, 2.8 miles from City Center, for live music and fresh seafood daily.

Where to stay in Siesta Key

The best areas and neighborhoods for your vacation rental in Siesta Key.

Siesta Key Village

Central hub with shops, eateries, and nightlife. Walkable area with lots of beach access.

Best for: nightlife lovers,families,foodies

Crescent Beach

Known for its excellent snorkeling spots and quieter beaches. Perfect for families and sunbathers.

Best for: families,beachgoers,nature lovers

Turtle Beach

More secluded area with picnic grounds and boat launch. Great for camping and kayaking.

Best for: adventurers,nature enthusiasts

Sarasota Mainland

Just across the bridge, offering shopping malls and cultural attractions. Only 6 miles from Siesta Key.

Best for: shoppers,culture seekers

Find Siesta Key vacation rentals that suit your style

Condos, vacation homes, bungalows and more — pick the kind of Siesta Key vacation rental you want, then book it direct with the host.

Siesta Key vacation rentals with free WiFi, hot tub or air conditioning

Free WiFi, hot tub, air conditioning and more — every Siesta Key vacation rental here is listed by a verified host and bookable direct, with the price the host set.

Top attractions in Siesta Key

All within driving distance of Siesta Key vacation rentals.

Siesta Beach

Famed for its sugar-white sand and clear waters. · 2 miles

Crescent Beach

Popular for snorkeling and dolphin watching. · 3 miles

Point of Rocks

Offers a unique geological spot for diving. · 3.5 miles

Siesta Key Farmers Market

Open Sundays for fresh produce and local crafts. · 0 miles

Siesta Key Village

Buzzing nightlife with bars and restaurants. · 0 miles

Big Sarasota Pass

Ideal location for fishing and boating. · 4 miles

Getting to and around Siesta Key

Driving or biking are popular for getting around Siesta Key.

Airports
SOUTHWEST FLORIDA INTERNATIONAL AIRPORT
Located 75 miles away, with many domestic and international flights.
SARASOTA-BRADENTON INTERNATIONAL AIRPORT
Only 10 miles from Siesta Key, ideal for quick domestic flights.
Driving
RENTAL CARS
Available at nearby airports and throughout Sarasota.
LOCAL TAXIS
Taxis and rideshare services offer convenient island transport.
Biking
BIKE RENTALS
Available in Siesta Key Village for easy access to beaches.

Similar vacation rentals near Siesta Key

Homes within 60 miles of Siesta Key, from verified hosts.

Condo in Beachfront Resort with Heated Pool

1 bd·1 ba
5· 29

$607.94 USD total for 3 nights

Sep 26 – 29, 2026

Hart's Paradise @ Barefoot Beach

1 bd·1 ba
4.77· 82

$526.89 USD total for 3 nights

Sep 27 – 30, 2026

Panoramic Gulf View with Amazing Sunset.

1 bd·1 ba
4.87· 223

$1,227.18 USD total for 3 nights

Sep 29 – Oct 2, 2026

Gorgeous Beach Home with heated pool

3 bd·3 ba
5· 9

$14,029.39 USD total for 28 nights

Sep 23 – Oct 21, 2026

Turtle Crawl Inn 64

1 bd·1 ba
4.88· 73

Tampa Event Compound, Hot Tub Bar

10 bd·10 ba
5· 48

$21,590.00 USD $18,426.50 USD total for 7 nights

Sep 23 – 30, 2026

Turtle Crawl Inn 63

0 bd·1 ba
4.74· 88

$861.06 USD total for 3 nights

Sep 24 – 27, 2026

Funshine Sunset Beach - Steps from the beach!!

1 bd·1 ba
5· 142

$538.86 USD total for 3 nights

Oct 3 – 6, 2026

Southern Exposure, Gulf Access, Heated Pool/Spa

4 bd·2 ba
5· 73

$2,520.39 USD total for 7 nights

Oct 3 – 10, 2026

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

6 bd· ba
5· 55

$5,989.00 USD $5,546.04 USD total for 3 nights

Sep 23 – 26, 2026

Craig House with Heated Pool

3 bd·2 ba
4.8· 107

$1,150.60 USD $1,104.12 USD total for 5 nights

Oct 6 – 11, 2026

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