Siesta Key Vacation Rentals with Boat Dock

(43 rentals)
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Key Amenities

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

About this property

Nicely decorated and spacious two bed/two bath 4th floor unit in sought after Midnight Cove condominium community. Located directly on Crescent Beach on Siesta Key. Unit has 1500 sq. ft. under air with a large screened lanai that spans across front overlooking the beach. Porcelain tile throughout, ...

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Property Type

Siesta Key Condo

"Beautiful Condo in Midnight Cove - Siesta Key"

Always a great visit to Siesta Key. Midnight Cove is always as nice as it gets. Holly is tremendous to work with on our rental. Can't wait to get back!

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2 BR | 2 BA | Sleeps 6 | Quick View

14
Owner special: Winter is coming but the cold doesn't have too! VISIT NOVEMEBER 12-19 Email us about this great deal

$287

avg/night

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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

"Location!!!Location!!!!Location!!!Outstanding!!!"

A108 is one of the nicest condos we have ever rented. The recent renovations are above & beyond expectations. Everything is first class. The condo is literally 15-20 steps to the beach. Can’t get any ...

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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.4 miles to Siesta Key Beach

$450

avg/night

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Key Amenities

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

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 ...

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Property Type

Siesta Key House

"Home Away from Home/Great Location"

We loved the location of this home. Not only because it’s located on a canal and very private, but it’s only a two-minute walk to Siesta Key Village. The beach is also a short walk of only 6-7 minutes. ...

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Key Amenities

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

About this property

There is no way you can get closer to the water than this! Sitting outside and having your morning coffee listening to the waves is so relaxing. Having a glass of wine and watching the sun set is the perfect way to end the day. This amazing unit has it all! The Primary bedroom has a king bed and its ...

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Property Type

Siesta Key Condo

"Wonderful condo"

We stayed at this condo and loved our stay. The ocean was so close beautiful sunsets and everything one would need for a wonderful stay. There are many fishermen hence why it’s called fisherman’s dove ...

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1 BR | 1 BA | Sleeps 4 | Quick View

13
LAST MINUTE DEAL 9/16 - 10/28: THE BEACH IS CALLING YOU! DECEMBER-PERFECT WEATHER! EMAIL US ABOUT THIS GREAT DEAL!!!!

$240

avg/night

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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

"Fun in the Sun"

Our rental unit B309 was wonderful, as was our stay on Turtle Beach! We have stayed in many beachfront properties, but this was ideal! The beach was literally outside our door! Walk down the steps and ...

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DEAL

2 BR | 2 BA | Sleeps 6 | Quick View

2

$270

avg/night

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Key Amenities

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

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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Property Type

Siesta Key Condo

"Wonderful Place!"

The entire condo appeared to be newly remodeled. It was beautiful! For any beach goer the location can't be beat. Siesta Key is across the street. This was truly a home away from home. Exceptionally clean ...

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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

"Paradise Found!!"

We were excited to spend a week in Florida. The condo made our vacation the ultimate paradise getaway!! This condo was very clean and beautifully decorated! Eating our meals in the lanai with that view ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Vacation rental with private beach on the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)*** STAY SAFE *** In response to COVID-19, additional safety and sanitation measures are taken ***Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is ...

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Property Type

Siesta Key Apartment

"Beautiful view"

Siesta Key is a favorite. The convenience of walking a short and healthy walk to the white sand is a plus. The property management was quick to take care of a few concerns we had upon arrival to make ...

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2 BR | 2 BA | Sleeps 6 | Quick View

15
LAST MINUTE DEAL 9/16 - 10/28: Winter is coming but the cold doesn't have too! VISIT NOVEMEBER 12-19 Email us about this great deal

$287

avg/night

View Details

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 100 ...

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Property Type

Siesta Key Condo

"Beachfront Escape"

This location was absolutely perfect. Exceptionally clean, well stocked. Family-friendly condo. Will definitely return. Ms. Dina was a pleasure to worked with.

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DEAL

2 BR | 1.5 BA | Sleeps 4 | Quick View

25

Distance to beach: 200 yards to Crescent Siesta Key Beach

$174

avg/night

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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

"Amazing"

The condo was fabulous. The location was great, the gated community was real nice. Private pool, tennis courts and a private beach with the free chair and umbrellas for the day. Sunsets we did see were ...

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2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.2 miles to Siesta Key

$340

avg/night

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Key Amenities

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

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach . ...

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Property Type

Siesta Key Condo

"Awesome condo!"

Loved everything about the condo and the grounds! Great pool area and views everywhere! Condo has all you need and owner was great to work with! Can't wait to be back!

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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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2 BR | 2 BA | Sleeps 6 | Quick View

4

$286

avg/night

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Key Amenities

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

About this property

This colorful custom 3rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! This is an adults only unit, perfect for a mature couple who can take excellent care of things and appreciate the fine nature of this unit.From the modern ...

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Property Type

Siesta Key Condo

"AMAZING view!"

This condo has it all! This is the first condo I have ever stayed at that had ALL the kitchen utinsels you could ever need (minus and Instant Pot, but it does have a crockpot)! The view makes it seem ...

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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

"Peaceful"

Really enjoyed staying at this quieter end of the island. It was a much needed break. Carrie is very sweet and easy to deal with. Will definitely be returning again.

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2 BR | 2 BA | Sleeps 4 | Quick View

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

$155

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 5 | Quick View

4

Distance to beach: 0.0 miles to Siesta Key beach also known as "Crescent Beach"

$253

avg/night

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Key Amenities

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

About this property

Spectacular remodel with open concept design maximizing beach views and sounds. The million dollar view you always wanted and can now enjoy.Fully equipped modern, clean kitchen with beach view, stainless steel appliances, ice maker, dish washer, granite counters and back splashes and custom cabinets.Secure ...

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Property Type

Siesta Key Condo

"Absolutely beautiful condo"

This condo is absolutely incredible. It is beautifully decorated and well kept. The views from the lanai are simply breathtaking. We enjoyed every second of our stay and cannot wait to go back!!

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4 BR | 3 BA | Sleeps 8 | Quick View

$332

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

Very nice 4 Bedroom home on a canal just about 5 blocks to Siesta Village. offering: 1 car garage, Duet washer/ dryer, Private pool, decorated with a Island flare. Tile throughout and nice granite and stainless kitchen. Beautiful setting pool and patio overlooking Canal with boat dock. 3 TV's, 1 DVD, ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

43

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

$268

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 condo with a beautiful view and sound"

The week I spent at Condo-309A was a true dream vacation for my daughter and I. It's beautifully furnished and has everything you need to cook or to enjoy the beach. The owners are very gracious. You can ...

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Key Amenities

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

About this property

This colorful and well cared for unit has a new owner! The view from your lanai will include sunset and will be magnificent! No other property on Siesta Key is built this close to the Gulf of Mexico where you can hear the waves from your lanai and master bedroom windows. The furnishings are very comfortable ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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Property Type

Siesta Key Townhome

"Midnight Cove"

We stayed at Midnight Cove for spring break. Our condo was very nice! It overlooked the pool and the bay. The whole complex is beautiful and it was actually very quiet at night considering it was spring ...

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2 BR | 2 BA | Sleeps 5 | Quick View

12

Distance to beach: 400 yards to Crescent Beach

$208

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

"Loved EVERYTHING about this place!!!"

This was our first time vacationing in Siesta. I inquired on the Siesta Key community FB group. Chris, the owner of Villa E8 at Horizons West responded immediately to my inquiry. He made himself available ...

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3 BR | 3 BA | Sleeps 6 | Quick View

3

$314

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.1 miles to Crescent Beach Siesta Key

$185

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to The Anchorage Yacht and Tennis Club across from the beautiful sands of Crescent Beach on Siesta Key. Sitting directly on the intercoastal waterway where you can park your boat, jet ski, kayak, and paddleboard. This complex has an Olympic size pool, three lighted tennis courts, pickleball nets. ...

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Property Type

Siesta Key Condo

"June Trip"

Check in was easy. Clean unit. Management staff were friendly and helpful. Beach area use could be more clear. The beach accessories were good.

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2 BR | 2 BA | Sleeps 5 | Quick View

2

Distance to beach: 0.0 miles to Siesta Key beach also know as "Crescent Beach"

$275

avg/night

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Key Amenities

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

About this property

Best beachfront view on Siesta Key from remodeled two bedroom and two bathroom beachfront condo. Stay for the unbelievably beautiful beachfront balcony views. Enjoy the modern open floor plan with beach views from most rooms. Beautifully furnished apartment you will be proud of.Upgraded, secure WiFi.Spectacular ...

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Property Type

Siesta Key Condo

"Any last minute availability for February"

Hello I was looking to see if you had any last minute availability for February ? Sorry to contact through the review I could not find an email address to send a request. Thank you for your time best Joann

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1 BR | 1 BA | Sleeps 2 | Quick View

1

$229

avg/night

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Key Amenities

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

About this property

Perfect location to relax and enjoy your Siesta Key tropical vacation or get away. Enjoy breath-taking sunsets from the your own screened lanai with beautiful water views.Comfortable 1 bedroom (king size bed), ground floor condo located directly on Turtle Beach Inlet where you can fish, swim, paddle ...

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Property Type

Siesta Key Apartment

"Wonderful!"

Nothing short of spectacular! The condo was nicely decorated, well stocked and the bed was extremely comfortable! Walk out of the lanai and your at the pool just beyound the pool is the intercoastal where ...

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 800 feet to Siesta Key Beach

$167

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
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

"Jamaica Royal"

We loved our stay here. Right on the beach and great pool close to our condo. Clean and spacious. Maybe could use a few updates but we were mainly here at night for sleeping so it worked well for us.

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5 BR | 4 BA | Sleeps 13 | Quick View

10

Distance to beach: 400 feet to Siesta Beach

$698

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

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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Property Type

Siesta Key House

"Best vacation"

Perfect house! The beach is right there! The house is gorgeous and had everything we needed for the beach! 18 years of vacationing with friends and family and this was just perfect! David is fantastic ...

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2 BR | 1.5 BA | Sleeps 5 | Quick View

Distance to beach: 250 feet to Siesta Key

$174

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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Key Amenities

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

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 Mexico. A lovely spot to watch sunsets. The unit is upgraded and comfortable for couples traveling together or with ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

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

$260

avg/night

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Key Amenities

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

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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Property Type

Siesta Key Condo

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Key Amenities

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

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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Property Type

Siesta Key Condo

"happy vacation"

great bay pool just liked watching boats go by and a lovely atmosphere family friendly air went out and owner had contact maintenance was repaired quick

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Key Amenities

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

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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Property Type

Siesta Key Condo

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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

"Florida"

Great place to be for Christmas break and New Year love Florida weather and definitely will be back for another vacation

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2 BR | 2 BA | Sleeps 6 | Quick View

1
LAST MINUTE DEAL 9/24 - 10/1: Last week in September is open for reservations at a 20% discount. Upscale 5 star rated property.

Distance to beach: 30 feet to Turtle Beach

$250

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront

About this property

Within just a few feet of the beach, our condominium home features a well equipped kitchen with granite counter tops, luxury vinyl flooring, a leather sectional couch, recliner chairs, teak furnishings, ceiling fans in all rooms, a 55 inch smart TV in the living room and a flat screen TV in each bedroom ...

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Property Type

Siesta Key Condo

"Beautiful Condo right on top of the beach."

Condo is perfect for my family. Clean, well equipped and so close to the water. We like this quiet part of Siesta Key, but only 10 minutes to the village. People that live here are very nice and helpful ...

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DEAL

Key Amenities

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

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

"Perfect Condo for Family"

This was our first visit to Turtle Beach and the location of this condo is perfect! Bay in the front and beach in the back. The condo was clean and had everything we could possibly need. The beds were comfortable ...

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2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 30 yards to Turtle Beach

$260

avg/night

View Details

Key Amenities

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

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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Property Type

Siesta Key Condo

"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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3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 0.5 miles to Siesta Beach access 7

$250

avg/night

View Details

Key Amenities

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

About this property

*Calendar month rentals only*June - November (six-month lease) - $3500 per month plus utilities June - November (three-month lease) - $4500 per month plus utilities December - $6500 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month ...

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Property Type

Siesta Key Bungalow

"My stay at the Canal Place in Siesta Bungalows"

I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta ...

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1 BR | 1 BA | Sleeps 2 | Quick View

4

Distance to beach: 0.5 miles to Siesta Key Beach

$132

avg/night

View Details

Key Amenities

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

About this property

*Calendar month rentals only*May - November (seven-month lease) - $1995 per month plus utilities May - October (three-month lease) - $2900 per month plus utilities December - $3500 per month plus utilities January, February, and March - $5500 per month plus utilities April - $4500 per month plus ...

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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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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

You have access to a private deeded walkway from your condo to the white sand and turquoise waters of Siesta Beach/Crescent 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 ...

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Property Type

Siesta Key Condo

"Paul and Sue from Lancaster New York"

The condo exceeded all expectations! The owners have provided a beautiful home away from home. Starting the day with breakfast on the lanai overlooking the intercoastal followed by a short walk to Florida's ...

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2 BR | 1.5 BA | Sleeps 4 | Quick View

Distance to beach: 950 feet to Crescent Beach

$150

avg/night

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Key Amenities

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

About this property

Direct-with-Owner Rental Discounts: Midnight Cove #714 offers "All-In Price" 15% to 30% Discounted Rental Rates from $871 to $2,126 /Wk Depending on the Season ($130 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $214 to $675 /Wk from the listed ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 3 | Quick View

6

Distance to beach: 0.5 miles to Siesta Key Main Beach

$128

avg/night

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Key Amenities

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

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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Property Type

Siesta Key Condo

"Love them"

We are staying here all summer and it's amazing. Barbara is so nice and renting her unit was easy. Its an amazing place with everything you need. The place exceeds standards. She was very accommodating. ...

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2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 200 yards to Siesta Key Crescent Beach

$185

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

We invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal sands of Crescent Beach on Siesta Key. Siesta Chillin has been recently updated and has all the conveniences of home in an amazing vacation spot at The Anchorage Yacht and Tennis Club.When ...

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Property Type

Siesta Key Condo

"Beach condo"

Condo was in a great location with easy beach and bay access. Plenty of room for a family of 5. Grocery stores and dining within driving distance. Older unit, but in adequate repair and clean.

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Siesta Key Vacation Rentals