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Siesta Key Condo Rentals

(101 rentals)
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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$198
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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$138
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

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

About this property

Fisherman's Cove Condominiums have the best Location on Siesta Key! It is surrounded by water with the Gulf of Mexico on the west side and a private lagoon that leads to the inter-coastal waterway (ICW) on the east side. Swim, surf, boat, kayak, paddle board, fish, gather seashells and shark’s...

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Featured review

"Gorgeous oasis!"

First floor walk out directly on the beach. I had seen photos of the brand new overhaul, however I was not prepared to be over whelmed by the beauty when we walked in. It literally took my breath away!...

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$281
avg per night
Siesta Key Condo
Sleeps 8, 2 bedrooms, 2 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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$457
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private 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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Featured review

"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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$264
avg per night

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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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$239
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beautifully renovated one bedroom King size super comfy mattress. Full bathroom with shower/tub. Fully remodeled kitchen with dishwasher. Living room has queen size memory foam sleeper sofa. Comfortably sleeps 4. Free parking, wi-fi, smart TVs in bed and living room. Heated pool, tiki hut on the bay,...

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Featured review

"Truly a five star condo!"

We just returned from our getaway at Varinia’s home. It was perfect in every way. Short walk to the pool, short walk to the beach and all needs were met. The beach wagon, chairs and umbrellas were excellent...

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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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$211
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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$191
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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$267
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 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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$312
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 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
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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$173
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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$404
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
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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$158
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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$239
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

A211 is gorgeous, newly renovated with brand new kitchen, appliances and cabinets, living room, dining room and bathrooms (all with new walls, ceilings, doors and tiled floors). Also available is a new in-unit large capacity washer and dryer. The kitchen is fully equipped with many of the comforts of...

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$239
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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$156
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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$202
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool

About this property

The Condo Bay side water views; 2nd floorPrimary: King BedPrimary bath: tub/shower comboGuest: 2 twins/convert to KingGuest bath: tub/shower comboLiving Room: Sleeper Sofa

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$178
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

Are you ready to stay directly on the water? The sunsets are beautiful and the Gulf is so refreshing. We look forward to hosting you and your guests!Within just a few feet of the shore, our condominium home features a well equipped kitchen with granite counter tops, luxury vinyl flooring, a leather...

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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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$240
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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$239
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 your beachfront escape at Fisherman's Cove on beautiful Turtle Beach, Siesta Key.This colorful and inviting first-floor condo comfortably accommodates up to six guests and offers the convenience of direct beach access just steps from your private lanai. Relax in the comfortable patio...

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$239
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

MONTHLY RENTAL. Introducing our BEAUTIFUL NEWLY RENOVATED LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need to cross any streets.Our home away from home is perfect for those seeking a winter retreat or...

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Featured review

"Wonderful hosts Beautiful Unit"

Chris and Jeannie could not have been more accomodating hosts . The unit was beautiful and well appointed. Residents of the Casarina were extremely friendly. Looking very much forward to returning next...

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$313
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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$147
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

Key Amenities

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

About this property

Roomy 2 bedroom, 2 full bath condo in prime Siesta Key location. Comfortably furnished living room, dining area, all linens and fully equipped kitchen included, ceiling fans in all rooms, Flat screen tv in living room with DVD player and a flat screen in the master bedroom. Master bedroom has queen-size...

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Featured review

"Comfortable unit"

The property was nice and comfortable. The children enjoyed the pool that was close to the unit. Owner promptly responds if we had questions.

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$258
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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$239
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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$210
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

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 to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on the...

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$202
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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$239
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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$174
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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$239
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Beautiful 4th floor condo with gulf views, a private beach, and a private fishing pier. This space was completely renovated in 2020 with all new features (including central AC) and furniture throughout. The fully-stocked kitchen is equipped with everything you need for a home-cooked meal. With a king...

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Featured review

"Great Location"

Half a mile walk to Siesta Key Village. We had a wonderfully updated condo. Maria and her husband were great landlords. We had a beautiful view every morning of the sunrise and every night on the private...

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$250
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Be prepared to relax as soon as you walk into our completely remodeled, bright open concept, 2BR, 2BA ground floor condo. Just a five minute walk to the beach. In addition to a king and two twin beds, there is a very comfortable pull out queen bed that doubles as a luxurious leather couch. The living...

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$231
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to Siesta Key Paradise! * available for winter/spring 2026* Your home away from home. Located in a prime spot on the quiet end of Siesta Key, this recently updated two-bedroom, two-bathroom is a great getaway.The condo is located at Mariners Inlet, which is an 8-unit complex located directly...

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$295
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1 bathroom
12 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo,...

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Featured review

"Another wonderful holiday on Siesta Key!"

Thank you again, Barbara and Angelo, for providing your vacation home for our annual trip to Siesta Key. November is our favorite month there, with perfect temperatures and a tranquil setting. The property...

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$108
avg per night
Siesta Key Condo
Sleeps 2, 1 bedroom, 1 bathroom
10 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

You have access to a deeded walkway from your condo to the beach while living directly on the intercoastal waterway with a great view. The intercoastal waterway, with its parade of all types of boats and dolphins swimming by, is visible from practically every room. This 2nd floor, 1 Bedroom/1 Bath...

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Featured review

"Great!"

Wonderful location for boat watching and easy access to the beach. Owners are lovely and super easy to work with.

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$239
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 250 feet to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Direct-with-Owner Rentals: Siesta Breakers #603 offers "All-In Price" 10% to 25% Discounted Rental Rates from $2,095 to $3,921 /Wk Depending on the Season and payment method ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $366 to $855 /Wk from...

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Featured review

"Lovely"

The condo was very clean and comfortable. Beautiful view from the lanai. Great location, walking distance to many restaurants and ice cream parlors!

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$317
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 0.1 miles to Siesta Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Our new unit are truly a site to see. 2 BR / 2 BATH completely remodeled, newly furnished unit with fully equipped kitchen, cable TV, WiFi, and washer/dryer. Enjoy a Resort Style pool area beautifully landscaped with 2 Tiki Bars and plenty of space to work on your tan! Not to mention a grassed area for...

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Featured review

"perfection!"

Roomy, very clean, very accommodating staff. Pool was super clean and warm. Walk to everything., don't need a rental car!

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$250
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry...

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Featured review

"Very nice host and home. Home needs work."

The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed...

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$140
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 1.5 bathrooms
2 reviews

Distance to beach: 850 feet to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Direct-with-Owner Rental Discounts: Midnight Cove #532 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

"Great stay in siesta keys"

This 2 bedroom ground floor condo was comfortable, clean, stylish and centrally located. It was fully stocked eith cleaning and cooking supplies as well as hairdryer and iron. We had a great time and...

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$144
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 200 yards to Siesta Key Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

SIESTA SUMMER SAVINGS! RECEIVE 10% OFF YOUR SUMMER STAY BETWEEN 5/30/26 AND 8/29/26 WHEN BOOKING DIRECTLY ONLINE AT THE ANCHORAGE YACHT & TENNIS CLUB IN-HOUSE RENTAL PROGRAM WEBSITEWe invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal...

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Featured review

"Siesta Central - The Anchorage!!"

We stayed at the Anchorage in unit 305. It faces the city and the inner coastal lagoon. We were treated to a dolphin show one evening when they entered the lagoon searching for food!! This location...

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$192
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.3 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Renovated 2BR (one queen size & 2 single beds) 2 Bathrooms 2nd floor condo and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paved stones drive and covered parking, newly installed luxury wood-like flooring a comfortable...

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Featured review

"Beautiful condo"

We spent a month at this beautiful condo. It was very well equipped with everything we needed. Lovely warm pool and such a short walk to Siesta Key Beach. Thank you Lynette (the owner) for making this...

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$155
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

Your home away from home on Siesta Key with 2 bedrooms 100 steps to the beach. This fabulous condo features a comfortable king bed, a full bed, and a twin bed, perfect for families or friends traveling together. Guests enjoy two bathrooms, each equipped with a refreshing shower and a hair dryer for convenience....

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Featured review

"A Siesta Key - Gem!"

A truly perfect condo on the beach with fantastic views of Crescent Beach and Siesta Key Beach. This ocean view unit, also overlooks the largest pool of three available on this well landscaped, large gated...

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$200
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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$144
avg per night
New
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Available October 15, 2026 through March 15, 2027. The ideal rental is the full seasonal period, although other stays of two months or longer may be considered.Spend the winter where everything is within walking distance.Welcome to your home away from home in Villa Navarra, an intimate 16-unit...

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$162
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.MESSAGE ME FOR LINK TO THE BOOKING WEBSITE AND...

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Featured review

"Awesome stay!"

Had a great time at White Sands #308. Close to the beach and a very nice pool with grills! Super easy to get around with the trolly and “frog hop” so you don’t have to drive. Highly recommend.

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$180
avg per night
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