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Siesta Key Vacation Rentals

(193 rentals)
Siesta Key Apartment
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Second floor, 2 bedroom/2.5 bathroom townhome located in the quiet complex of Bay Oaks. Unit is nicely furnished with plenty of space. Tile flooring in kitchen, dining room and living room. 2 TVs with washer/dryer inside unit. 2 screened lanai's, small balcony and full kitchen. WIFI in unit. Complex...

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$158
avg per night
Siesta Key Villa
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come stay and relax on Siesta Key! Home of the #1 Beach in USA. Award winning white sand beaches await. Completely remodeled, 1 bedroom/1 bath, 1st floor condo with private screened lanai with new pergo floors and new kitchen. Washer/dryer in unit located just one block from the shops and restaurants...

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$224
avg per night
Siesta Key Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise on Siesta Key! This charming 2 bedroom/2 bath condo is just steps from the award-winning white sands of Siesta Key beach. Enclosed patio. Enjoy the refreshing pool and amenities like tennis and grilling. WIFI. No pets. Sleeps 4 (1 King, 2 Twins). 2-week minimum. Check in: 15:00 - 23:59 Check...

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$135
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
20 reviews

Key Amenities

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

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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Featured review

"Siesta Key Vaca"

We are lifetime residents in the area & haven't been to Turtle Beach/South Sieta Key for years. Fisherman's Cove was a great find for a week stay. Our unit was renovated in a fun beachy theme with nice...

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$285
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village...

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Featured review

"Great location!"

The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.

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$181
avg per night

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Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 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

"Great beach view"

Place is awesome and Kathy is best host.Right on beach and restaurants within walking distance. Had a couple of questions and Kathy got back to us right away. If you like the beach, you will love this place.

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$328
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

Key Amenities

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

About this property

Our gorgeous condo is surrounded by water with the Gulf of Mexico on one side and Blind Pass Lagoon on the other side and Sarasota Bay within kayak range! Such a unique setting, sitting at the southern and most private end of Siesta Key. A306 is on the third floor and the views are stunning! Our community...

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Featured review

"Spring break"

We very much enjoyed our time at fisherman's Cove. We loved the closeness to the beach and the quieter location! The condo was well stocked and appreciated the beach chairs and towels. We look forward to...

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$285
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to our vacation oasis. We love the peaceful, friendly vibe of the Bay Oaks community and hope you do as well. Our two bedroom, two bathroom second floor condo unit has been recently upgraded with new living and dining room furniture and new bedding in relaxed but upscale style. The complex sits...

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$158
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

Waterfront Pool Home – Walk to Siesta Key Village & BeachPrime Siesta Key LocationWelcome to your private island getaway in the heart of Siesta Key.Located on a quiet waterfront street just steps from Siesta Key Village and a short walk to the world-famous white sand beaches, this...

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Featured review

"Siesta Key home"

This home is in one of the best locations on Siesta Key. It’s a little bit older style of a beach house beds were comfortable outside furniture and inside furniture could use some updating. I think they’re...

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$295
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come relax in this quiet bayside complex that is surrounded by whispering oaks. 2nd floor unit is a 2 bedroom/2 bath remodeled unit. Complex offers tennis courts, community pool and pier for fishing. Unit has tile in main traffic areas with carpet in bedrooms. Leather sofa, open kitchen wit granite countertops....

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$158
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

Key Amenities

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

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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Featured review

"perfect spot"

Fisherman's cove is the ultimate spot for a peaceful getaway. Your host Carrie is a wonderful, warm and thoughtful person. You won't find anyone better. Her condo Is perfectly located on the corner of the...

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$256
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
10 reviews

Key Amenities

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

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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Featured review

"all that and a box of chocolates"

crescent royal condos was top notch condo 409 was as clean as a surgical room the view was better than I expected beach beyond perfect location perfect if your looking for a great place this is it

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$207
avg per night
Special Offer
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
30 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

"Condo at siesta key"

Rented our condo from Christina it was everything she said it was. Condo very nice beds super comfy had a great time there would rent again.

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$150
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 queen size bedrooms, 2 bathroom , second floor end unit, adjacent from the pool, available for rent. Laundry availalbe on the first floor of the building. short walk to the ocean. Quiet and private space to relax and enjoy.

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$171
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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$219
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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Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This first floor colorful unit sleeps 6 and you will love the sandy beach just outside the lanai door with comfortable patio chairs. Walk past the dune to enjoy more beach and the Gulf of America. A lovely spot to watch sunsets. The unit is upgraded and comfortable for couples traveling together or with...

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Featured review

"Seista Key 2026"

Property was under reconstruction after storm last time I was there. It is now ready for rental. I intemt to travel there next week and will stay for the month.

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$255
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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$233
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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$171
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 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

"Fantastic location"

Our family loved staying here and have already looked into coming back! The location can’t be beat as it is on the first floor of the tower which makes the beach just steps from your door. We enjoyed...

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$207
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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$279
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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$230
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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$181
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

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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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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$240
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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$177
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 0.3 miles to Siesta

Key Amenities

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

About this property

Enjoy resort amenities at the Harbor Towers tennis and Yacht club in Siesta key. The building has completed a $13 million dollar structural and cosmetic renovation and is a beautiful building highlighting Siesta key and Midnight Pass. This condo offers the option to play tennis, swim at the pool exercise...

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$138
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

AFTER 2 HURRICANES E91 IS READY FOR GUESTS!! We thank God that our condo was spared! 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...

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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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$174
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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$157
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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$231
avg per night
Special Offer
Siesta Key Villa
Sleeps 6, 2 bedrooms, 1 bathroom
10 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

"Enjoyable VacationVilla"

The Villa was perfect for my December trip to Siesta Key! Very clean, appreciated lots of towels (which I find a plus staying other places they skimp on them), kitchen well equipped. Access to the beach...

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$271
avg per night
Siesta Key Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 600 yards to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Our House on Siesta Key!There’s plenty of room for everyone here at Our House. The split-level living area features a large-screen HDTV, perfect for movie nights with popcorn and frosty drinks after a day of outdoor fun. Just steps away, the fully equipped kitchen has everything you...

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Featured review

"Great Stay"

We had a great stay at this condo. We would definitely stay here again. It was clean and spacious. It was also very close to siesta beach and near siesta village. Overall great experience!

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$208
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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$468
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This cozy beach house awaits your visit! Magnificent view of the Gulf of Mexico and evening sunset from lanai.... Peaceful Intercoastal inlet views and sunrise from front door...This little nest has been newly "stem to stern" furnished and equipped for your comfort. Coastal Living as its...

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Featured review

"Perfect sunsets, great lanai and best location"

Nice quiet location on Turtle Beach. Best sunset views, right on the beach and all the amenities one needs for a perfect beach holiday. Added bonus of docks for boats/kayaks, heated pool and gated entry....

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$255
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 400 feet to Siesta Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Prime location, being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor...

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Featured review

"Fantastic place"

This home is absolutely beautiful and spotless! Has every amenity you could want and is so close to the beach! Working with the host was very easy and very accommodating. You would totally enjoy this stay,...

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$530
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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$158
avg per night
Siesta Key Apartment
Sleeps 4, 2 bedrooms, 1.5 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Vacation rental close to the # 1 beach in the US - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.Whether you are looking for a perfect destination for your vacation, a romantic...

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Featured review

"Perfect"

We spent 18 days at the unit. The Unit is beautiful and clean. We enjoyed the location and hope to return next year.

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$148
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 100 feet to Siesta Key - Across the Street!

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Looking for the perfect beach getaway? Discover your dream vacation at this beautiful 2 bedroom, 2 bath condo only steps away from the world-famous white sands of Siesta Beach! Perfect for couples or families. Only 3/4 mile from Siesta Key Village which boasts great restaurants and shopping. View...

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$218
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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$709
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 20 feet to Turtle Beach, Siesta Key

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful beach inspired decor...Fresh, airy and calm...perfect relaxing unit with all the comforts of home and more to enjoy a fun filled time at the beach!!!!!

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$255
avg per night
Siesta Key House
Sleeps 13, 5 bedrooms, 4 bathrooms
16 reviews

Distance to beach: 400 feet to Siesta Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway....

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Featured review

"Perfect Home for a Relaxing Siesta Key Getaway"

This house was perfect for our group. With five bedrooms and four bathrooms, everyone had plenty of space and privacy, and the layout made it easy for a larger group to spread out without feeling crowded.The...

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$837
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 30 feet to Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

We have made tremendous progress recovering from Hurricane Helene and are ready to welcome guests back to Fisherman's Cove. The sunsets are beautiful and the Gulf is refreshing. We look forward to hosting you and your guests!Within just a few feet of the shore, our condominium home features...

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Featured review

"Heaven on Earth"

Wonderful unit it was so well stocked and all accommodations we very good. we had brought a boat and everything needed was there. great vacation spot . Will come back again.

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$255
avg per night
Siesta Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.4 miles to Siesta Key Beach

Key Amenities

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

About this property

Location, location, location!! New pool and spa just completed! Waterfall edge from spa to pool and deck jets. New landscaping with additional seating areas near pool and canal. Also, lots of green space to enjoy too!Canal home in heart of the Siesta Key Village, no need for a car! Steps away from...

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Featured review

"Excellent"

The house was extremely clean and nothing was missing. Loved my stay from beginning to end. Melissa checked in a few times to make sure I was happy. I would stay at this home again. It has raised my bar...

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$637
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 30 yards to Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Bright and inviting, this popular unit has floor to ceiling sliding glass doors from the lanai, offering breathtaking third floor views. Beautiful white porcelain tile leads to new bamboo laminate flooring, which is just one of the many recent upgrades. The open kitchen has comfortable counter seating...

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Featured review

"Holmes Beach Rental"

We loved our visit and loved the condo. The views were amazing . The only compliant would be the living room furniture was not comfortable. And the kitchen could use more kitchen items. But we dealt with...

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$255
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
13 reviews

Distance to beach: 200 feet to across street

Key Amenities

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

About this property

2 bedroom gorgeous condo overlooking Siesta Key Beach and Gulf of Mexico. Complex with large community pool, sauna, covered parking, secure gated area. Gas grills, party room, beautiful property. 2 full bathrooms with granite walk in showers and basin, etc. King bed in master with ensuite full bath,...

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Featured review

"Perfect winter escape"

The view onto the beach is spectacular and relaxing. Easy to get to all services and attractions by walking, biking, or free buses. We will be back.

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$209
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Totally remodeled ground floor unit. This unit is brand new to the rental market and is a rare find. Walk out the rear Lanai door directly to the becach. You can't get any closer to the Gulf of America on Siesta Key. The open floor plan allows Gulf views from the sunroom, master bedroom, living room,...

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$255
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Enjoy the unrestricted views (no sea oats or berm) of the ocean and sunsets from our beach front condo just steps away from the Gulf of America. It is located on Turtle Beach known for its quiet, relaxing, low-key vibe. We have the most unique location on the island, the Sarasota Bay intercoastal waters...

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$255
avg per night
Siesta Key House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.9 miles to Siesta key

Key Amenities

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

About this property

Comfortable private 3bedroom 2 bath home, open concept floor plan. The master suite is large and open with a sitting area and views of the tropical garden in the back of the house, a full walk in closet and step down shower bath with dual vanities. The next bedroom consist of 2 twin beds with additional...

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Featured review

"Definitely more than 5 stars for this property"

I’ve rented several Siesta Key properties, but this is definitely my favorite. The home is located very close to the public beach down a quiet cul de sac. The neighbors were all friendly and the area...

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$294
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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$172
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Discover your own slice of paradise in this brand new 100% fully renovated 2-bedroom, 2-bathroom villa, with vaulted ceilings and an open floor plan. This villa is located in the vibrant heart of Siesta Key. This charming retreat blends modern amenities with a prime location, ensuring an unforgettable...

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$288
avg per night
Siesta Key Condo
Sleeps 2, 1 bedroom, 1 bathroom
10 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

Key Amenities

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

About this property

Sweet Siesta Key Condo walking distance to #1 Beach in America! Spacious and Quiet One Bedroom with King Bed, Screened Lanai, Wireless Internet, 2 Flat screen TV’s, covered parking space, full kitchen with amazing water filtration system. Easy Walk right over to Siesta Key Main Beach, and their...

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Featured review

"Great place to stay"

Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my...

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$134
avg per night
Full map
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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°

FAQ

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

There are 193 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to apartment 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 $67 per night with an average price per night of $255.

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 93 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 54 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!