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Siesta Key Vacation Rentals

(205 rentals)
Siesta Key is the eight-mile barrier island off Sarasota, with quartz sand so fine and white that U.S. News ranked Siesta Beach the best in the country. Its walkable Village lines a half-mile of Ocean Blvd with shops and dining Condos run a median of $306 a night; homes and villas sit at $392.
Siesta Key Condo
Sleeps 8, 2 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the gorgeous 2BR 3Bath beachfront townhouse nestled in the tranquil complex on Siesta Key, FL. Escape the big-city crowds and enjoy the lovely ambiance from the patio while being just a few steps from the pristine sandy beach, swimming pool, local restaurants, shops, and attractions. 2...

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$471
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 20 yards to Crescent Beach, Siesta Key

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean...

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$287
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
55 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your little piece of paradise on Siesta Key—an oceanfront condo where the view is the experience.This fully renovated 2-bedroom, 2-bath unit offers direct, unobstructed Gulf views from the living room, kitchen, master bedroom, and lanai. There are no angled views or buildings in the...

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Featured review

"Great Stay"

We had a great stay despite the weather. Amazing view!! The owners were great at communicating and really responsive. We’d love to return in the future.

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$505
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 1.5 bathrooms
2 reviews

Distance to beach: 950 feet to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Direct-with-Owner Rental Discounts: Midnight Cove #714 offers "All-In Price" 10% to 25% Discounted Rental Rates from $946 to $2,488 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $163 to $621 /Wk from the listed...

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Featured review

"Siesta Key Midnight Cove 714, Convienient, 1st Floor Condo, Great Complex"

Midnight Cove has all the amenities for a great getaway on Siesta Key. The complex has great beach access, beach chairs with attendant on the beach, nice pool ,fitness center and two BBQ grill areas. The...

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$207
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent) Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront...

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$320
avg per night

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Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
32 reviews

Distance to beach: 0.1 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Skip the parking hassle — you’re just steps from Siesta Key Beach, consistently ranked #1 in the U.S.This newly upgraded 2-bedroom, 2-bath condo is perfectly located directly across from the beach and minutes from Siesta Key Village. Walk, bike, or hop on the free trolley to reach top...

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Featured review

"No worries relaxation"

Responsive, informative credible host. Exact match to published stay info. Accommodations were exceptionally clean and comfortable. I felt as if I were home. The home has everything that you could ask for...

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$145
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 100 feet to On-site Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

One of the best locations at Fisherman's Cove, condo B-101 has a sandy beach area out our back lanai door and the community swimming pool six steps from our front door!As a result of the hurricane that impacted Siesta Key in 2024, our condo was entirely rebuilt from the stud walls in! Everything...

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$353
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 90 feet to In front of condo!

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The new owners have spared no expense in transforming this bright, inviting waterfront condo into a luxurious coastal retreat. Completely remodeled from top to bottom, the condo features new luxury flooring, solid-core six-panel doors, fresh paint, new light fixtures, ceiling fans, and beautifully rebuilt...

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$344
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FLCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront...

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$320
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 5 feet to Crescent Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

FULL GULF FRONT- Cathy's Crescent Condo-Beautiful turnkey 2nd floor condominium located on the pristine beaches of Siesta Key, FL. Voted the finest sand in the world. It doesn't get any better than this! This condominium is Full Gulf Front. You can view the water/beach while lying in bed from...

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Featured review

"Wonderful Views and Condo"

Absolutely beautiful view from every room. Wonderful sunsets every night and a few steps from the beach. Kathy is a great hostess and was very responsive to all of our questions. We are already planning...

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$392
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 0.1 miles to Crescent Beach on Siesta Key

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with private beach access and overlooking its own private harbor is the perfect getaway to the #1 beach on Siesta Key in Sarasota, Florida. This unit is located near the community pool and hot tub along with guest grilling...

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Featured review

"Easy and FUN Vacation"

The booking and check in process was easy. In addition , we appreciated how fully stocked and clean the condo was. Getting around the island was simple (walking and riding the tram). Best of all, the beach...

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$197
avg per night
Siesta Key Townhome
Sleeps 6, 3 bedrooms, 3 bathrooms
14 reviews

Distance to beach: 0.3 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Discover the ultimate Siesta Key getaway with this beautifully appointed, smoke free, 3-bedroom Townhouse, perfectly situated just 300 steps from the world-famous Crescent Beach. Enjoy the best of both worlds with Turtle Beach only 2.4 miles away, offering endless opportunities for seaside relaxation...

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Featured review

"Great location!!!"

The condo was great for our stay in Crescent beach for the month. It has everything you need to enjoy your stay at the beach. From beach chairs,bikes,umbrella's, towels and so much more. The pool was very...

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$421
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This stunning, fully remodeled 2-bedroom, 2-bathroom Siesta Key condo offers the ultimate beachfront escape. Located on the serene south end of Siesta Key in Fisherman’s Cove, the condo faces the Gulf of Mexico and is less than100 feet from the water. Enjoy beautiful tile flooring, a gourmet kitchen...

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Featured review

"Fall break vacation"

We brought our grandchildren down for fall break. We made lots of memories and had a great time. Perfect place to stay!

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$347
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Condo, 2 Bedrooms, 2 Baths, Sleep Sofa (Sleeps 4-6)If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. This is the ‘Best Location’ on ‘Crescent Beach.’ Experience...

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Featured review

"Spring Break 2026"

My daughter and I went down and enjoyed the place. The convenience to get to the beach was great and it was such a big area!! Loved walking around the key!! Love Siesta Key and this was a fabulous place...

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$426
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This tropical island get-away offers everything you desire for a magical, effortless vacation. Sunny, spacious second floor condo with easy indoor-outdoor living space including two queen bedrooms, each with an ensuite bathroom. Just steps to private, quiet powder-sand gulf beach and private fishing...

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Featured review

"Just perfect - a beautiful condo in a natural setting"

This is a lovely immaculate condo in a lush green setting. From my window i watched birds, ducks, and turtles on the lake . On the sweet private beach i saw pelicans, dolphins and egrets. It's tempting...

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$305
avg per night
Siesta Key Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building...

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$345
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and...

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Featured review

"Beautiful Bayside Condo"

This is a beautiful condo in Bayside Club resort. A gated community. Well cared for. This condo is just 30 feet from one of the pools, tennis courts and pickle ball courts. It’s a short walk to...

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$331
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
86 reviews

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation...

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Featured review

"Relaxation at the Beach with an Awesome View"

As we a stepped into the condo I was totally amazed by the view. It was the first thing i noticed and it drew me to the sunroom just to gaze at the ocean. Walking away from that view was hard but when i...

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$344
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat DocksLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLFisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the...

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Featured review

"First visit to Siesta Key"

Great location on Turtle Beach, quieter and less busy than Siesta Key Beach. Great accommodations direct access to beach with boat slip out back to get out onto Sarasota bay. Nicely equipped condo, although...

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$305
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen...

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Featured review

"Amazing Stay"

My family and I had the most amazing stay in Don & Elaine’s condo! We have been coming to Siesta Key for 6 years and this was our favorite room- best location and best view ever! We look forward to returning....

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$405
avg per night
Siesta Key Condo
Sleeps 10, 4 bedrooms, 4.5 bathrooms
3 reviews

Distance to beach: 0.3 miles to Siesta Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This 4 bedroom 4.5 bathroom condo with elevator, pool and private beach access. No need to look any further as luxury awaits! There is a wonderful outdoor living space with dining table and lounging area, living room, dining area, kitchen, office as well as laundry room. All of the bedrooms have an ensuite...

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Featured review

"Great condo and location"

Thanks to Stephanie for excellent communication and special thanks to MJ who was very helpful and quickly available during our stay. This condo is beautiful and has an excellent location. It's a 3 minute...

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$778
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 0.1 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This amazing condo offers a Gourmet Kitchen and island. Granite counter tops, high ceilings and stainless steel appliances (including super quiet Bosch dishwasher and French door refrigerator with two ice-makers).Removed and replaced all forty year old Duct-work with brand new Flex Duct-work for improved...

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$355
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
52 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This magnificent unit is on the third floor with spectacular unobstructed views of the Gulf! This unit has been completely renovated with beautiful natural stone tile throughout, updated kitchen and bathroom and brand new furniture, coastal pictures, decorative accessories, bedding, new paint throughout....

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Featured review

"Absolutely perfect!"

The owners make your arrival amazing. You have to experience it to know. The view is breathtaking. Both the back of the property and the front have spectacular views. The property is perfectly equipped...

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$299
avg per night
Siesta Key Condo
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living....

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Featured review

"March Getaway!"

Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.

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$186
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1 bathroom
4 reviews

Distance to beach: 0.0 miles to Siesta Key Main Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Water views everywhere from this Penthouse condo on Siesta Key! Taxes (13%) already included in my rates. Walk to beach. King bed in bedroom (and a Queen bed in living room if needed). Come and enjoy beautiful weather at the best beach in Florida! Heated Pools, Lighted Har-Tru Tennis Courts, Fitness...

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Featured review

"Penthouse Paradise"

what a great find! A bright and lovely penthouse condo in a resort on Siesta Key. Easy walk to the beach, and the new Pickleball courts at the Main beach. Harbor Towers itself had a great pool, marina,...

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$279
avg per night
Siesta Key Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This spacious, beautifully decorated and updated 2 BR/2.5 bath townhome overlooks the canal and boat basins and is located directly across the street from the gorgeous Siesta Beach. The kitchen and all baths have been renovated and the newly furnished living room features a sofa bed and 55” smart...

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Featured review

"Paradise Found"

My family absolutely loved this home. We’ve been traveling to Florida for almost 10 years and have stayed in many different rentals. This was our second year in Siesta Key, we loved it so much we came...

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$243
avg per night
Siesta Key House
Sleeps 10, 4 bedrooms, 3 bathrooms

Distance to beach: 0.6 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your slice of paradise on Siesta Key—where coastal charm meets everyday convenience. This beautifully maintained single-family pool home offers the perfect blend of privacy, comfort, and proximity to the island’s natural beauty. Step outside and enjoy the lush, landscaped backyard,...

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$392
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Crystal Sands, Siesta Key, SarasotaReduced summer rates.Amazing Views!! Our property is right on the beach. Take the elevator down and you're at the ocean. The views are amazing as you can see in the pics. Sit on the lanai for breakfast and watch the activities on the beach, or have a glass...

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Featured review

"AMAZING 2-Weeks!!!!!"

We loved every minute of our 2-week stay at Crystal Sands, the unit was beautiful and views breathtaking. We were a stones throw from the beach and it couldn't have been any better. I highly recommend!

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$434
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Summer Cove on Siesta Key is life at its finest. This gated community on Little Sarasota Bay offers a spacious 2 bedroom, 2 1/2 bath unit of luxury with the sophistication and conveniences of the finest resort located on the Key within minutes to the #1 beach in the US - Siesta Key Beach. The unit is...

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$405
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Located in beautiful Siesta Key, Fl. this bayside condo is full of amenities needed for a relaxing beach vacation. Two tennis courts with Pickleball available, two heated pools, covered private parking, outdoor gas grills, boat docks, outdoor bathrooms within this private, gated community.Walk to...

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Featured review

"Fantastic"

Very family friendly, had beach toys and beach towels available, along with a beach tote. Host provided us a pack and play on request. Beautiful bay facing condo and easy walk to gulf side.

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$338
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.

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Featured review

"A lovely styled and very well presented unit"

Beautifully refurbished and meticulously maintained, this property offers the perfect beachside getaway. Inside, you’ll find plenty of space, excellent storage, and a fully equipped, sparkling clean kitchen.The...

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$276
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

Distance to beach: 1 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

E91 is a completely renovated, First floor Condo, steps to the pool. Master bedroom has a King bed with on-suite bathroom and walk-in closet. Second bedroom has a Queen bed and twin bunk beds. Fully equipped kitchen provides state-of-the art appliances. There is washer and dryer conveniently by the kitchen. Ammenities...

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Featured review

"Best Condo EVER !!"

The HOST of this unit (E91) was the most prepared HOST of all time. She had every box checked inside the condo to make our stay effortless. The grand-children loved the bunk beds in the second bedroom...

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$226
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Completely remodeled private villa is steps to the famous white sand of Siesta Key Beach.Bedroom 1- King bed, en suite bathroom, TV Bedroom 2- 2 Queen beds, en suite bathroom, TVOpen-concept Living, Dining, Kitchen with counter seating. Large TV for everyone to watch movies & games. Fully...

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$331
avg per night
Siesta Key Villa
Sleeps 5, 2 bedrooms, 2 bathrooms
17 reviews

Distance to beach: 400 yards to Crescent Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to The Sand Dollar, a beautifully maintained beach-to-bay villa in the sought-after Horizons West community on Siesta Key. All the amenities of a resort, with the privacy and charm of a standalone beach villa.Start your morning with coffee overlooking the Intracoastal Waterway, spend the day...

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Featured review

"Beautiful villa"

Villa E8 was attractively decorated and well equipped. Property was clean and well maintained. Property management company was very responsive. Weekly linen service was a nice surprise.

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$260
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 1 bathroom
11 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your slice of paradise in Siesta Key! Our updated 2-bedroom, 1-bath villa is just two villas away from the private, powdery white sands of Crescent Beach, ranked the #1 beach in the U.S. by both Dr. Beach and TripAdvisor. Enjoy complimentary cabanas and lounge chairs while soaking up the Florida...

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Featured review

"Like paradise"

Looking forward to returning in the fall. So beautiful and so much to do. Great vacation spot. Villa is the perfect size for us and the grandkids enjoy it too!! Our favorite place to vacation!

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$258
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
7 reviews

Distance to beach: 100 yards to Crescent Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a queen memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for your...

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Featured review

"Great Beach Condo"

Great Location. Walk to beach and pool. Walking distance to Capt. Kirks seafood restaurant. Very quiet. Plenty of stores, restaurants, and bars would definitely go back anytime.

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$280
avg per night
New
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Escape to your private coastal retreat on world-famous Siesta Key. This beautifully remodeled 5th-floor condo pairs luxury living with unmatched tranquility, offering sweeping views and resort-style amenities in a quiet, exclusive community. (3 month minimum lease required)Premium Amenities•...

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$217
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
17 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Located on siesta Key in Sarasota, FL. The Palm Bay Club has two heated pools both Bayside and Gulfside. A private marina, dock, spa, tennis courts, fitness rooms and is located on Crescent Beach voted number one beach USA 2014Sarasota is located approximately 40 minutes South of Tampa. 1 1/2 hour...

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Featured review

"Palm Bay"

Very convenient to ICW and about 1/2 mile to the beach. Very comfortable condo and the owner was very responsive and proactive with the information we needed.

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$182
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
12 reviews

Distance to beach: 0.3 miles to Crescent Beach on Siesta Key

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal...

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Featured review

"Paradise on the Bay with Easy Beach Access"

We absolutely loved our stay in Siesta Key! The location was beautiful, with an incredible view of the bay right outside our door. Staying on the ground floor made the experience even more special… every...

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$211
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 1.5 bathrooms
6 reviews

Distance to beach: 200 yards to Siesta Key/ Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our vacation home is just steps away from the #1 rated beach in the USA - Siesta Key beach. It is unit B07 in the Casa Blanca resort located on the GULFSIDE (or Beach side) of the island.It is a comfortable villa with a master bedroom, guest bedroom, living room, kitchen with dining area, and a...

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Featured review

"Our Casa Blanca experience"

This was our second vacation in as many years at Casa Blanca. Both times we selected the same unit number and both times we were simply delighted with the experience. Everything exceeded our expectations....

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$266
avg per night
Siesta Key Condo
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.1 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Fully renovated penthouse unit! This property seamlessly melds state of the art amenities with casual beachfront living with privacy. Step off of the sugary sands of Siesta Key Beach and right in to this beautifully renovated beachfront condominium with surprisingly expansive gulf views. Sea and sky...

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Featured review

"Heaven"

I think this is what Heaven must be like.. Our stay here was wonderful! This is a beautifully renovated, clean, and comfortable unit. It is the whole top floor of a two unit building (no elevator; 27 steps...

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$1,000
avg per night
New
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Villa 412 at Siesta Sands offers a comfortable coastal escape where relaxation comes naturally. Bright and airy, this inviting villa features an open floor plan with a light, beach-inspired atmosphere that creates an easygoing setting from the moment you arrive. The well-equipped kitchen and welcoming...

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$426
avg per night
New
Siesta Key Villa
Sleeps 6, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Enjoy a relaxing stay at this simple yet cozy 2-bedroom, 1.5-bathroom villa located just minutes from the beach. Perfect for families, couples, or small groups, this comfortable space offers everything you need for a stress-free getaway. The primary bedroom features a comfortable king-size bed, while...

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$221
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 800 feet to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master...

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$177
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.7 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

**Completely Renovated February 2025** Welcome to island life! Enjoy your own private resort in the heart of the #1 beach in America, Siesta Key!Indulge in the pinnacle of island living at this pristine waterfront home on Siesta Key—a haven where luxury meets natural beauty. In the heart of...

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Featured review

"Beautiful and comfy"

5 stars. Wish I could give 10. Beautiful and comfy cozy home, comfortable beds, gorgeous pool, so kid friendly and lovely views from the fire pit. The decor is top notch!! Danielle and Jeb were great-...

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$599
avg per night
New
Siesta Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Enjoy comfort and convenience in this well-appointed 2-bedroom, 2-bathroom villa located in Casa Blanca, just minutes from the beach, dining, and island attractions. The primary bedroom features a king-size bed with an en-suite bathroom and shower, offering privacy and relaxation. The guest bedroom includes...

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$249
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Newly remodeled kitchen with stainless appliances. Freshly painted throughout and casual furnishings for your family to enjoy. First floor for quick access to the beach from your lanai door. New drapes at the sliding doors separating the living room and lanai. Renovated master bath and guest bath. The...

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$306
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 1.5 bathrooms
2 reviews

Distance to beach: 250 feet to Siesta Key

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis...

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Featured review

"Perfect"

This was our third stay in this apartment, and everything was perfect as always! Great location, fully equipped with everything you need, and the rental process was easy and hassle-free. Thank you! We would...

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$205
avg per night
New
Siesta Key Villa
Sleeps 6, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Escape to the perfect beachside retreat at our charming and spacious two-bedroom condo on beautiful Siesta Key. Just steps from the world-renowned white sands of Siesta Beach, this inviting getaway is ideal for families, couples, or friends looking to relax in comfort and style. The condo features two...

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$182
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to a bit of heaven!A gorgeous gulf-front vacation awaits you as you come and enjoy this enchanting condo! Located directly on beautiful Turtle Beach in Siesta Key and just steps away outside your door. There is no other resort complex like this that is so close to the beach!As you travel...

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$306
avg per night
Full map
Map

What staying in Siesta Key actually costs

Owners list their cleaning fees, taxes, and any extra charges up front, and because you book with the owner directly, you skip the booking fee the large travel sites add. Sarasota County adds a 13% tax on stays under six months.

SHORT STAY
3 nights

$1,283

all in
$428/night

$310 × 3 nights$930
Cleaning + damage waiver$205
Tax (13%)$148
Booking fee$0
Total$1,283

WEEKLY STAY
7 nights

$2,597

all in
$371/night

$299 × 7 nights$2,093
Cleaning + damage waiver$205
Tax (13%)$299
Booking fee$0
Total$2,597

MONTHLY STAY
30 nights

$9,113

all in
$304/night

$262 × 30 nights$7,860
Cleaning + damage waiver$205
Tax (13%)$1,048
Booking fee$0
Total$9,113

When to visit Siesta Key

The Gulf here has two busy stretches: Snowbirds fill the cool, dry winter, and families crowd the warm summer months. For swimming weather without the peak-summer heat or the June-through-November hurricane season, aim for April and May or October, when the Gulf sits in the mid-70s to low 80s and the days stay warm and dry. September, at the height of hurricane season, is the quietest and cheapest month.

Peak rates Best value Shoulder Gulf water temperature
MonthMedian nightlyDifference from annualHigh / low air tempAvg. gulf tempWhat’s going on
January$310+9%71° / 51°64°Peak snowbird season; Sunday farmers market in the Village (year-round)
February$393+38%74° / 54°65°Cortez Fishing Festival, 35 minutes north
March$407+43%77° / 58°67°Sarasota Jazz Festival, mainland
April$330+16%81° / 62°73°Run/Walk for the Turtles; Sarasota Film Festival
May$259-9%86° / 68°78°Sea-turtle nesting begins, lights-out rule
June$2850%89° / 73°82°Summer family crowds arrive
July$2850%91° / 74°85°Fourth of July fireworks on Siesta Beach
August$250-12%91° / 75°87°Red tide possible along the coast
September$233-18%89° / 73°85°Peak hurricane season, lowest rates
October$233-18%85° / 67°82°Sea-turtle nesting season ends
November$235-18%79° / 60°75°Crystal Classic sand-sculpting on Siesta Beach
December$275-4%74° / 54°69°Christmas Boat Parade of Lights

Based on the median Siesta Key nightly rate on FloridaRentals.com.


Where to stay in Siesta Key

Siesta Key runs about eight miles, and its three beaches each anchor a different part of the island. Public beach accesses are numbered 1 through 13, but for a beach with a lifeguard, head to the main Siesta Public Beach.

Map of Siesta Key, Florida vacation rental areas
SIESTA KEY
Lido Key
Sarasota
Palmer Point
Gulf of Mexico
Roberts Bay
Little Sarasota Bay
Big Sarasota Pass
Midnight Pass Rd.
Stickney Point Rd.
Beach Rd.
Siesta Beach
Crescent Beach
Point of Rocks
Turtle Beach
Gulf Coast
2 km / 1.2 mi
Siesta Key in three areas: Siesta Beach and Siesta Key Village at the north end; Crescent Beach and Point of Rocks in the middle; and Turtle Beach at the south end. Coastline, roads and beaches © OpenStreetMap contributors; Florida outline: US Census TIGERweb.
Siesta Beach & the Village
The island's north end, where Siesta Key Village packs restaurants, bars and a late-night scene into four walkable blocks around Ocean Boulevard and Canal Road. Siesta Beach, named the No. 1 beach in the country by U.S. News & World Report in 2026, is a short walk away, and White Sands Village is five minutes from the sand.
Crescent Beach & Point of Rocks
South of Siesta Beach, Crescent Beach curves down to the rocky headland at Point of Rocks. This is resort country, about 1.5 to 2.5 miles south of the Village: beachfront communities like Crescent Arms sit directly on the sand, and gated resorts such as Gulf and Bay Club keep a private strip of the beach.
Turtle Beach
The quieter south end of the island along Midnight Pass Road, between the Gulf and Little Sarasota Bay, running down toward Palmer Point. Stays here are mostly low-key homes and smaller complexes, farther from the Village's restaurants and nightlife, and a good fit if you want quiet nights.

Popular Siesta Key resorts

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Things worth doing in Siesta Key

Sunday drum circle
Sunday drum circle
A free, drop-in drum circle forms every Sunday about an hour before sunset, just south of the main pavilion between lifeguard stands 3 and 4.
Siesta Beach
Point of Rocks
Point of Rocks
Snorkel the shallow water over the limestone ledges at the south end of Crescent Beach, reached from Beach Access 12. Bring your own gear.
Crescent Beach
Kayak and paddleboard
Kayak and paddleboard
Launch from the Turtle Beach boat ramp into Blind Pass and the calm bay water. Rentals are available on the bay side of the island.
Turtle Beach
Siesta Beach day
Siesta Beach day
The wide, powder-fine quartz sand stays cool underfoot, and the Gulf stays calm and shallow a long way out, which makes it great for kids.
Siesta Beach
Village dining
Village dining
Eat at the Siesta Key Oyster Bar or The Old Salty Dog, two long-running spots on the Village's walkable half-mile of Ocean Blvd.
Siesta Key Village

Know before you book

Fly into Sarasota-Bradenton, about 20 minutes out.

Sarasota-Bradenton International (SRQ) is the close commercial gateway, about 20 minutes from the island. Tampa International (TPA) is about an hour and 15 minutes north with far more flights, worth it only if it fits your route better.

The free 77 Siesta Islander trolley covers the island.

It runs on-island between Siesta Key Village and Turtle Beach, daily from about 8 a.m. to 10 p.m., and everyone rides free. For off-strip stays and quick trips to Turtle Beach, a car helps. Siesta Beach's main lot is free but fills fast.

Dogs aren't allowed on Siesta Key's beaches.

Sarasota County's ordinance bars dogs from the sand, with an exception for service dogs. The nearest off-leash dog beach is Brohard Paw Park in Venice, about 35 minutes south.

Houses may have longer minimum stays.

Sarasota County bars rentals under 30 days except on Residential Multi-Family barrier-island parcels, which is why island condos can host short stays while many single-family homes carry a 30-day minimum.


Siesta Key vacation rental FAQs

Straight answers to what people ask us most.

How much does a vacation rental on Siesta Key cost?

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The median vacation rental on Siesta Key runs about $310/night, or roughly $2,093 for a week and $7,860 for a month. Condos run a median of $306 a night, while homes and villas sit at $392.

What's the cheapest month to visit Siesta Key?

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September is the cheapest month, because it falls at the height of hurricane season, when demand is lowest. For warm Gulf water and drier weather without paying peak rates, April, May, and October are the better value.

Is Siesta Key the same as Siesta Key Village?

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No. Siesta Key is the whole barrier island and the destination. Siesta Key Village is one walkable district at the north end, a half-mile of Ocean Blvd lined with shops, bars, and restaurants. If the Village is where you want to be, book there.

Can I bring my dog, and are dogs allowed on Siesta Key beach?

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You can bring a dog to a pet-friendly rental, but Sarasota County bars dogs from Siesta Key's beaches, service dogs aside. So plan on a dog-free beach day or a drive off the key when the dog needs sand of its own.

Do I need a car on Siesta Key?

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You don't need a car to navigate the island. The free trolley links the Village and Turtle Beach, and the Village is walkable. However, a car is helpful for day trips off the key, like to Sarasota or the Ringling.

Is Siesta Key good for families with young kids?

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Yes. Siesta Beach has a shaded playground, picnic pavilions, and lifeguards, all a short walk from the main free lot. For a quieter day, Turtle Beach at the south end is calmer and good for shelling.

Nearby cities and how they compare

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