Siesta Key Vacation Rentals

(239 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located 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 is one of the closest condos ...

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Property Type

Siesta Key Condo

"Beautiful Condo in a nice quiet area a stone's throw from the beach."

We loved this condo. It was beautiful, newly refurbished and so comfortable. More like a nice family home than just a rental. We loved sitting in the sun on the lanai watching the birds and the beach. ...

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1 BR | 1 BA | Sleeps 3 | Quick View

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

$296

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

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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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

"Wonderfully Relaxing"

Staff, wonderful, front desk also wonderful. Snythyou need is a call away. Condo comfortable and clean

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2 BR | 2 BA | Sleeps 6 | Quick View

6

Distance to beach: 1 miles to Crescent Beach

$206

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

NEW ON SIESTA KEY RENTAL!! Completely renovated First floor Condo. Two bedrooms 2 baths - very close 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 with state-of-the art appliances. ...

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Property Type

Siesta Key Condo

"Wonderful condo"

This unit at Bay Oaks was very clean and in a great location. It’s within walking distance to the south village of Siesta Key and the trolley stop to the north village is right out front. The beautiful ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This magnificent unit has been completely remodeled and is on the ground floor with beautiful water views and spectacular sunsets. Walk out the rear lanai door directly onto the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf of Mexico within 100 ...

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Property Type

Siesta Key Condo

"Paradise"

Our family spent the first week of April basking in the sun on Turtle Beach. We thoroughly enjoyed our week’s stay at this beautiful spacious 2 bedroom 2bath condo on the Gulf of Mexico. The condo was ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Enjoy easy living and carefree days on Siesta Key! This modern bungalow is steps away from the private, deep, white sand beach of Aloha Kai and the only solar-heated, Olympic-sized pool on the Key. Have your morning coffee or afternoon cocktails on the airy lanai or relax in the bright mid-century modern ...

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Property Type

Siesta Key Bungalow

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$292

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large ...

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Property Type

Siesta Key Condo

"Beautiful Condo!"

This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen ...

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 100 yards to Turtle Beach

$269

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Enjoy your home away from home in beautiful Siesta Key! This great 2-bedroom, 2-bath has everything you need for a wonderful, relaxing vacation. This prime location makes it convenient to get to the beach. Just walk a single flight of stairs (or elevator) and you're on the beach where you can enjoy ...

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Property Type

Siesta Key Condo

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Key Amenities

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

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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Property Type

Siesta Key Condo

"Beauty at the Beach"

I highly recommend condo 601 South/ Beauty at the Beach! Elaine was very accommodating and her condo was the most coziest, beautiful, and relaxing place that I have stayed in a very long time. It had everything ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

The Gulf of Mexico is only 100 ft. from your private sand beach and lanai entrance. Listen to the surf from your master bedroom. Enjoy dining on the lanai while watching the sunset. During the day you can see dolphins, kite boarding and sea birds. This unit has all the comforts of home plus a full size ...

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Property Type

Siesta Key Condo

"Clean & Well Stocked"

Three very important things to make your vacation complete; cleanliness is number one of course, location and is the rental property well stocked so you have everything that is needed for a vacation of ...

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2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 400 yards to Siesta Beach

$215

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Spectacular long Siesta beach and Gulf of Mexico views from this gorgeous 2 BD, 2 bath unit. It has was fully remodel in a high quality fashion. The unit is furnished first class and with all the features you could want for a fun vacation! The resort style condominium has three pools, large ponds, lighted ...

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Property Type

Siesta Key Condo

"Great property !"

Beautiful home with all the amenities. Very private location on Azure Way in great neighborhood, but still close to beach & restaurants. Excellent communication with David & owners. Highly recommend.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within ...

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Property Type

Siesta Key Condo

"Better than ever"

Our second stay in 106B was fabulous, again! The unit is impeccable, fully appointed, and no amenity is overlooked. Being able to step out our door onto the sand is paradise for us. Thank you Dina for ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...

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Property Type

Siesta Key Condo

"What a Fantastic Little Gem!"

Siesta Key have become our favorite vacation spot and #409 at Crescent Royale was where my wife and I got to experience the very best thanks to Karen who accepted us in her beautiful and awesomely appointed ...

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2 BR | 2 BA | Sleeps 4 | Quick View

11

Distance to beach: 0.2 miles to Siesta Key Beach

$255

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. It is a lovely 2 bdr/2 bath unit with a spacious living room and sunny lanai. The master bedroom has full bathroom ...

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Property Type

Siesta Key Condo

"Gulf and Bay Bayside Unit #1344 D"

Lovely 2B/2B ground floor condo with fabulous sunroom getting morning sunshine. Sunroom faces a shell path that winds throughout the development and views lush landscape with blooming hibiscus bushes. Quiet ...

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2 BR | 2 BA | Sleeps 6 | Quick View

13

Distance to beach: 0.0 miles to Siesta Key Public Beach

$329

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

This 2-bedroom, 2 bath Siesta Key condo can sleep 6 comfortably with a pull-out queen sofa bed and total square feet of 1,773! The beautifully decorated updated condo, with newly tiled bathrooms offers a comfortable, home-away-from-home feel. Sit on your private 20 ft deck and enjoy the view of a lake ...

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Property Type

Siesta Key Condo

"Siesta Key get away"

We loved the beautiful condo. It was our first trip to Siesta Key and we enjoyed it thoroughly. The condo was well kept, fully furnished for the most part and the Mgmt team was there to help us when we ...

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2 BR | 2 BA | Sleeps 5 | Quick View

15

Distance to beach: 400 yards to Crescent Beach

$280

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The Sand Dollar is a private villa located at the quiet, well run and exceedingly clean "beach to bay" community of Horizons West. A maximum of 50% of Horizons West properties are rented so the community has a more residential feel than many others on the island. The villa has been recently ...

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Property Type

Siesta Key Villa

"Cozy and comfortable!"

This is the second year that we have stayed at the Sand Dollar House. From the moment we arrived, we were greeted with warmth and hospitality. The attention to detail in the decor and amenities made us ...

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2 BR | 2 BA | Sleeps 6 | Quick View

72

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

$291

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

"Beautiful Beachfront Condo"

Fisherman Cove is great beachfront location on Turtle Beach. Dina and Russ have A309 beautifully decorated with beach accents. The view of the gulf is amazing and you are literally steps away from the beach ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

"Cold escape"

We always enjoy our stay at Gulf and Bay Bayside!!! Condos are perfect! We always meet new people who have become friends and can’t wait to see them again next year!!!

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1 BR | 1 BA | Sleeps 2 | Quick View

4

Distance to beach: 0.5 miles to Siesta Key Beach

$150

avg/night

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Key Amenities

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

About this property

*Calendar month rentals only*******SPECIAL***** April 2024 - $150/night plus utilities - 7 nights min**********May - November (seven-month lease) - $2000 per month plus utilities May - October (three-month lease) - $2900 per month plus utilities December - $4900 per month plus utilities January, ...

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Property Type

Siesta Key Cottage

"Excellent pet-friendly bungalow"

This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where ...

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2 BR | 2 BA | Sleeps 6 | Quick View

6

$284

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This colorful custom2rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! unit, perfect for people who can take excellent care of things and appreciate the fine nature of this unit.From the modern kitchen, you will enjoy Siesta ...

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Property Type

Siesta Key Condo

"Wonderful Vacation"

This was a terrific place to stay with wonderful views of the gulf. It was a very pleasant and peaceful trip. Carrie was great to work with. Once she found out about a beach project date changing, she came ...

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3 BR | 2 BA | Sleeps 6 | Quick View

1

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

$415

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover 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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Property Type

Siesta Key Condo

"Stunning Condo"

My family stayed in this stunning condo and absolutely loved it. Beautiful views, fabulous modern furniture, high tech TVs and sound system, awesome high end kitchen and baths.

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2 BR | 2 BA | Sleeps 5 | Quick View

5

Distance to beach: 100 feet to Crescent Beach

$333

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date ...

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Property Type

Siesta Key Condo

"Perfect"

Siesta Breakers is the perfect place to get away. This condo was wonderful and had everything we needed! You couldn’t ask for more beauty, comfort, and relaxation! This is the perfect place.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

"Fisherman's cove at turtle Beach"

This is I think my fifth year in this unit. It is always clean and very well equipped. Since it's right on the beach and has a wonderful view of the Gulf I think it's a fantastic plac e to stay. The people ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

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. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the ...

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Property Type

Siesta Key Condo

"Beware of Horrible Communication"

My husband and I intended to stay here in early February. On several occasions we reached out to customer service regarding damage from the hurricane. A letter was sent that only said “some amenities ...

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 800 feet to Siesta Key Beach

$160

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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Property Type

Siesta Key Condo

"Beach and ocean waves"

The condo was super nice. The master bedroom mattress was amazing for a rental. So often I feel like they are hard as rocks but this one wasn’t. The second bedroom had similar mattress but they were not ...

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Key Amenities

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

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

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Property Type

Siesta Key Condo

"Excellent Condo A306"

We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. Everything ...

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Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.0 miles to Siesta Key Main Beach

$149

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

PENTHOUSE WATER VIEWS! Available for Guest Rentals June through December, occupied January-May. Rates already include taxes. Sweet Penthouse Studio Condo on Siesta Key with Spectacular Water Views everywhere. Truly, my photos do not do these views justice....This is resort living on beautiful Siesta ...

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Property Type

Siesta Key Condo

"Great Visit! We will be back!"

Everything thing about this experience was great. Location, apartment, pool, walk to beach and the host’s responsiveness was exactly what we needed. Will definitely book with Sue again.

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1 BR | 1 BA | Sleeps 4 | Quick View

6

Distance to beach: 100 yards to Crescent Beach

$224

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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 Lazyboy queen memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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Property Type

Siesta Key Condo

"Sea Crest #26"

Great people. Great weather. Great beach access, loved the sunsets. TV had no directions on how to navigate. Loved being close to Captain Curt’s restaurant. Loved the Old Florida charm.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located 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 is one of the closest condos ...

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Property Type

Siesta Key Condo

"GREAT!!"

These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.

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2 BR | 1.5 BA | Sleeps 4 | Quick View

29
owner special
Owner special: Fall 2024 dates available!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$177

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

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Property Type

Siesta Key Condo

"Great Siesta Key Condo"

We stayed for two weeks with our family. The condo has everything you need. It is close to the pool, tennis and pickle ball. Complimentary trolly stops in front of property. Nicely decorated. Highly ...

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2 BR | 1.5 BA | Sleeps 5 | Quick View

Distance to beach: 250 feet to Siesta Key

$192

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 6 | Quick View

3

$314

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Great house on Siesta key with pool and kanal. You can do fishing on the backside or have a jetski, boat there. Sometime you can see seacows on the kanal. 3 bedroom with 3 bath and a nice heated pool tp play in. Nice and quiet place it is, and so close to the Village and beach. Enjoy the place.

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Property Type

Siesta Key House

"Perfect Location"

Located close to the village and within walking distance of the beach. Plenty of room for families and amenities which included bikes for all ages. The pool is heated and such a great perk!

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4 BR | 2.5 BA | Sleeps 8 | Quick View

8
last minute deal
LAST MINUTE DEAL 5/4 - 5/11: One week beach vacations on Siesta Key starting May 4 & June 1 - One night free = 14% discount

$761

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened ...

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Property Type

Siesta Key House

"Beautiful View Great Location"

Perfect oceanfront stay! Group of 8 (4 adults and 4 children under 10). Fit our 2 families perfectly and is only steps from the beach making it easy to run back and forth. Close to all shops/ice cream/restaurants. ...

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DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the ...

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Property Type

Siesta Key Condo

"good place"

Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate

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3 BR | 3.5 BA | Sleeps 5 | Quick View

5

Distance to beach: 0.3 miles to Crescent Beach

$344

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

6828 Midnight Pass Road is a townhouse style condo three level unit with 3 main bedrooms plus a bonus bath and laundry on the ground floor. Each bedroom has a queen bed, and all furniture and mattresses were purchased new in 2020. Brand new exterior paint and roof in 2024.Convenient and Easy: 3-minute ...

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Property Type

Siesta Key Townhome

"Best vacation ever!!"

We cant say enough about how beautiful this townhouse was, fully stocked with everything, (the blender was great to have because we love our mudslides out by the private pool) The location was unbelievable, ...

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2 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 0.0 miles to Siesta Key

$305

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Escape to your private oasis on Siesta Key! This spacious villa offers the best of both worlds: direct access to the #1-rated Siesta Key Beach through your own private beach area, and stunning views of the Intracoastal Waterway where you can watch boats go by or launch your own kayak.Unwind in comfort ...

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Property Type

Siesta Key Villa

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Updated 2 bedroom unit in charming Casarina complex is located directly on the crystal white sands of Siesta Key Beach. Amenities galore! Magnificent gulf views. Enjoy the serenity of this casual, comfortable and tastefully decorated home away from home. You will enjoy having the In unit laundry, ...

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Property Type

Siesta Key Condo

"Lovely condo!"

This condo is lovely! It is spacious, with great sunset/beach views, beautifully and comfortably furnished, and very well equipped and supplied. Excellent location on Siesta Key - half way between both ...

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Key Amenities

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

About this property

My ground floor rental is directly on the beach on the Gulf of Mexico, with incredible views and sunsets!The lanai has a back door directly out to the Beach. The front of my unit faces the Lagoon where we have a FREE DOCK for your boat or other water craft. (So you have water views in both directions)! ...

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Property Type

Siesta Key Condo

"Amazing"

This unit offers an amazing view of the ocean and sunsets. Perfect get away spot, great location, clean and has everything you need to enjoy your stay. We will be back in 2014!

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Gorgeous unit and beautifully furnished with an incredible 2nd floor view of the Gulf of Mexico. Sleeps six comfortably with a king master and a full size bed along with a twin in the guest room, plus a queen sleeper sofa. Two DVD players with movie collection; a CD player and CD collection; & beach ...

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Property Type

Siesta Key Condo

"Almost perfect"

I say this because, the weather was unbearably hot, (heat index some days 110) Everyday was 95 or higher. However the condo was comfortable, cute and the most beautiful veiw of the ocean. The lanai doors ...

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$315

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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 is one of ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

March 2024 availability, won't last long, please contact us! This condo has not been a rental in the past, so you will not see reviews yet - but you can see our property management reviews on Florida Rentals #1258, #11647, #11646 & #11645! This vacation rental condo is directly on the beach ...

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Property Type

Siesta Key Condo

"Siesta Key gem"

Excellent location right on the beach. Condo was very clean, spacious and well-appointed. Everything we needed for our stay was there for us. Hosts couldn’t have been more accommodating. Looking forward ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

NEWLY RENOVATED IN 2023!!VERY SPACIOUS 4 BEDROOM 2 BATHROOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS,VILLA SLEEPS 8, 1 KING, 1 QUEEN, ...

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Property Type

Siesta Key Villa

"AMAZING"

This villa was very spacious, clean, homey and comfortable. It was well stocked in all areas. The garage was filled with anything you would need to go to the beach. The beds were the most comfortable beds ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 1 miles to Turtle Beach

$153

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

This waterfront 3 bedroom Bungalow is nestled in an upscale area on Siesta Key between Turtle Beach (1 mi.), Crescent Beach (.5 mi.) and Siesta Key Beach (3 mi.) Free trolley can transport you to the beaches and restaurant in The Village. Enjoy your private dock on beautiful Heron Lagoon watching the ...

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Property Type

Siesta Key House

"Interior Designer"

The Bungalow is well designed as a beachy vibe...great location right on Midnight Pass. It is located at the quieter end of the key which we found more relaxing...great walking. The owners of the Bungalow ...

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2 BR | 2 BA | Sleeps 4 | Quick View

17

Distance to beach: 0.1 miles to Siesta Key Beach

$225

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

NEWLY UPGRADED - BEAUTIFUL CONDO FOR THE PERFECT GETAWAY FROM THE COLD Right across from Siesta Key Beach, minutes from Siesta Key Village - or the South Village - shopping, top restaurants, live music, and entertainment. Walk , bike or take the free trolley.Sit on the balcony for a quiet and ...

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Property Type

Siesta Key Condo

"Amazing"

This rental property was perfect for our family!! It’s located directly across from the beach access and there are plenty of beach chairs, toys and umbrellas that are supplied. You can easily walk downtown ...

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1 BR | 1 BA | Sleeps 3 | Quick View

8

Distance to beach: 150 yards to Crescent Beach

$295

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

1 Week Minimum Stay Required except during Feb 1 to the first Saturday after Easter when 2 weeks are required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great ...

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Property Type

Siesta Key Condo

"Georgious Siesta Key Condo"

This condo is perfectly located in the middle of Siesta Key, on the beach. It is a short distance to Siesta Key Village, that has shopping and restaurants. The condo is very comfortable, with up to date ...

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3 BR | 3 BA | Sleeps 6 | Quick View

8

Distance to beach: 0.3 miles to Crescent Beach

$402

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome to your perfect vacation home on Siesta Key! Our turnkey townhouse is located just a few minutes' walk from the #1 ranked Crescent Beach, where you can enjoy the crystal-clear waters and powdery white sand that have made Siesta Key world famous.Our townhouse features a spacious courtyard ...

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Property Type

Siesta Key Townhome

"Paradise!"

The place was immaculate and had everything we needed. It was so nice to have beach towels, chairs, and sand toys provided. The location is perfect. It's a very short walk to the beach. Some restaurants ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

This outstanding condo, A203, is on the second floor, accessible using the elevator or outside stairwell and is completely renovated with modern tile flooring throughout, updated kitchen and baths, and new furniture! The kitchen has granite counter tops with tiled back splash, and modern appliances including ...

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Property Type

Siesta Key Condo

"Seventh year in A203"

We loved our month stay on Turtle Beach. Fisherman’s Cove is definitely a golden nugget. A203 rented thru Endless Summer is a beautiful condo with everything you need. Thank you Dina & crew for treating ...

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2 BR | 2 BA | Sleeps 5 | Quick View

36
last minute deal
LAST MINUTE DEAL 5/11 - 5/18: Save $1000 May 11-18th or May 25th - June 2nd!

$538

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

The condo benefits from its own private pool. The living room, master bedroom, kitchen, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a beautiful couch to curl ...

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Property Type

Siesta Key Condo

"Fabulous Beachfront Siesta Key Condo"

We had a glorious week at Kevin and Elaine’s condo at Fisherman’s Cove. The location was perfectly private, steps to the beach. Condo was well appointed with everything we needed. Sunsets were to die ...

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DEAL

2 BR | 1.5 BA | Sleeps 6 | Quick View

6

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

$294

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Villa

"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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Siesta Key Vacation Rentals

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

Find the Beach Vacation of a Lifetime with Siesta Key Vacation Rentals


Interested in a beach vacation for your next spring break or a long weekend away? Though the great state of Florida is known for its many scenic beach towns, there are some that cater more to those looking for a quiet, relaxing trip and some that are perfect for an exciting vacation full of non-stop fun in the sun. What if you could find a beach city that offers the best of both worlds for a truly well-rounded vacation? Enter Siesta Key vacation rentals. 

Nestled just south of Sarasota, Siesta Key, FL, is a spirited city along the Gulf Coast that offers just as many opportunities for R&R as it does for nightlife, watersports, and unforgettable adventures in the great outdoors. Though the island of Siesta Key itself is only about eight miles long, it’s jam-packed with enticing restaurants, unique shops, and glittering white sand beaches as far as the eye can see. 

As a major vacation destination along Florida’s Gulf Coast, there are many hotel options to choose from during your stay, with varying proximities to the beach. However, if you’re looking for a truly immersive experience during your trip to Siesta Key, you won’t get it at a crowded commercial hotel! 

Browse Siesta Key vacation rentals from FloridaRentals to find the perfect rental home for your beach vacation. Whether you’re looking for a sunny, romantic getaway for you and a loved one, or you’re bringing the whole family along, you’re sure to find an incredible property. Look for one that offers authentic local architecture, plenty of space to spread out during your downtime, and close proximity to all of the best features the city has to offer.

Siesta Key, Florida Travel Tips


There’s a reason why oceanside Florida cities like Siesta Key tend to be popular destinations during springtime. While temperatures may be warmest on average in the summer months, this time of year also has the highest levels of precipitation and humidity. Unfortunately, this makes it more difficult to enjoy outdoor activities. 

In mid to late spring, temperatures in the air and water are warm and comfortable without too much rain or humidity expected. This makes it easy to take part in all of your favorite pastimes, including surfing, boating, wakeboarding, or simply catching some rays on the sand. 

The closest airport to Siesta Key is the Sarasota/Bradenton International Airport, which lies around 11 miles north of the city center. Most visitors will fly into this airport for its easy access, though the area can also be reached relatively quickly by way of the Tampa International Airport.

How to Spend Your Vacation to Siesta Key House Rentals


It’s no surprise that most Siesta Key vacationers spend more time at the beach than anywhere else during their visits. The most popular beach destination is Siesta Key Beach, which was ranked the #1 Beach in the U.S. by TripAdvisor’s Traveler’s Choice Awards in 2020. The gentle waves, powdery white sand, ample parking, and plentiful concession stands are just some of the reasons why many visitors choose to lounge their day away at Siesta Key Beach. 
Those who are interested in an unforgettable outdoor experience shouldn’t miss out on a trip out on the water with Adventure Kayak Outfitters. You’ll have the choice of a guided kayak tour of the nearby Exotic Mangrove Tunnels or a kayak rental to make your own adventure. You’re sure to spot some incredible wildlife like dolphins, exotic birds, and manatees along the way.

Yearly Events in Siesta Key


Siesta Key is closely linked with the nearby city of Sarasota. The two cities share many of their annual events, creating even bigger and better celebrations for locals and tourists alike to enjoy. 

One annual event that’s already become a mainstay in the local culture is the Annual Downtown Sarasota Craft Festival. This unique arts and crafts show features a wide variety of media, including pottery, paintings, jewelry, photography, and much more, alongside the scenic white-sand beaches. Visitors can peruse and purchase unique wares from local artisans, including soaps, spices, plants, and even kettle corn. 
Runners visiting Siesta Key can get in a great workout while supporting a great cause at the Annual Andrew Monroe Memorial Scholarship 5K Run/Walk. All funds raised during this event are donated to the Sarasota Community Foundation Scholarship, which helps local athletes train to their full potential and achieve their goals.  

Best Eats Near Siesta Key Rentals


Whether you’re in need of some casual seaside grub for the family after a long day at the beach or looking forward to a romantic date night with your significant other, Siesta Key has a huge variety of delicious and eclectic eateries fit for every taste and occasion. 

For a hearty steak, you can’t do much better than Summer House Steak & Seafood. This stylish eatery offers sustainably sourced steaks alongside a variety of unique sides, salads, beverages, and desserts that are sure to satisfy. Additionally, Summer House offers a full menu of seafood dishes. It takes full advantage of the city’s close proximity to fresh seafood and offers plenty of surf and turf options for hungry visitors. 

Island House Tap and Grill is a local favorite for casual yet memorable eats in Siesta Key. With a varied menu that includes everything from tacos to burgers to ceviche, as well as plenty of refreshing cocktails, you’re sure to enjoy a delicious and satisfying dinner with your family.


FAQ

How many vacation rentals are there in/around Siesta Key?

There are 239 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Siesta Key?

There are vacation rentals available in Siesta Key for as low as $90 per night with an average price per night of $269.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 57 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 53 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!