Siesta Key Rentals by Owner

(85 rentals)
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2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.4 miles to Siesta Key Beach

$462

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

"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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Key Amenities

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

About this property

The lifestyleLive the Siesta Key lifestyle: • Short walk to the beautiful white sand beaches • Linger in the vibrant cafes and shops of The Village • Kayak along the key’s Grand Canal • Spend afternoons relaxing in the pool • Enjoy Siesta’s famous sunsets ...

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Property Type

Siesta Key House

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Key Amenities

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

About this property

For more info, quotes, and instant booking visit us atWelcome to Palm View at Siesta Dunes! Kick off your shoes, grab a drink and enjoy the palm view (our condo's namesake!) of this beautiful and updated garden view unit. Our unit is not beachfront, but our complex is gulf side with 500ft of ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

11

Distance to beach: 200 feet to across street

$209

avg/night

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Key Amenities

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

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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Property Type

Siesta Key Condo

"Beautiful Property with Perfect View"

This property and the entire complex was perfect for our stay on Siesta Key. It was clean and well stocked with everything we needed. We would definitely stay again.

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Key Amenities

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

About this property

MONTHLY RENTAL. Introducing our BEAUTIFUL NEW 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 anyone seeking ...

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Property Type

Siesta Key Condo

"Casarina on Siesta Key: The perfect location for your perfect getaway!"

A short walk or Trolly ride from the heart of Siesta Key Village, this condo rental offers an unparalleled experience of home away from home and relaxation. From the moment you step into the beautifully ...

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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

"A perfect Vacatipon"

Our first time in Siesta Key and the excellent accommodations at the Palm Bay Club exceeded our expectations. The condo is exactly as shown in the pictures and provided all the amenities we needed with ...

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3 BR | 3 BA | Sleeps 6 | Quick View

7

Distance to beach: 200 feet to Siesta Key Public Beach

$292

avg/night

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Key Amenities

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

About this property

Single family home with private heated caged pool. Large open floor plan in living area to kitchen and enclosed pool and deck. 3 bedrooms, 2 of which are master suites with ensuite full baths, flat screen TV's, king beds, and sliding glass doors to either caged pool deck or open air sundeck. 3rd ...

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Property Type

Siesta Key House

"Siesta Beach"

Absolutely the best location! House was clean and has everything you need. Especially liked pulling wagon with all the beach items the short distance to the beach. Owners very helpful and quickly replaced ...

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$207

avg/night

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Key Amenities

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

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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Property Type

Siesta Key Condo

"Great location, great condo"

We really enjoyed our stay. the location was perfect, even though the weather wasn't as cooperative. Roy was very responsive both before and during the stay. We would definitely stay here again.

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Studio | 1 BA | Sleeps 4 | Quick View

3

$147

avg/night

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Key Amenities

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

About this property

We are proud of our Siesta Key Condo at Ebb Tide. This Florida Beach Rental is in the heart of Crescent Beach. Once you park your car there is no need to use a car for the rest of your stay. A short 1 1/2 block walk and your toes are enjoying the lush, white (quartz) sands of the crescent beach.The ...

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Property Type

Siesta Key Studio

"A little piece of Paradise."

The condo was absolutely amazing, and very affordable. Perfect for a couple, so close to the bay and the beach. The condo had everything needed for our stay. Will definitely book again. I love going to ...

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2 BR | 2 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$130

avg/night

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Key Amenities

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

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

"We Keep Coming Back"

It's all about The Lily Patch on Palm Island in the village of Siesta Key!!! We've love it so much that we've signed up again for 2021 (Winter #3) and sent in a donation to the neighborhood HOA this time. Bring ...

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3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 0.5 miles to Siesta Beach access 7

$226

avg/night

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Key Amenities

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

About this property

*Calendar month rentals only**********SPECIAL****** April 2024 - $6900 per month plus utilitiesMay-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 ...

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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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Key Amenities

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

About this property

Enjoy resort amenities at the Harbor and Yacht club in Siesta key. This condo offers the option to play tennis, swim at the pool exercise in the work out room or play pool in the social club. You can walk to the beautiful white sand of siesta key beach or catch a trolley to the village and shop or enjoy ...

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Property Type

Siesta Key Condo

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2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 950 feet to Crescent Beach

$202

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" 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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Property Type

Siesta Key Condo

"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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2 BR | 1.5 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.3 miles to Siesta Key Beach

$150

avg/night

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Key Amenities

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

About this property

*Calendar month rentals only*July- December (six-month lease) - $3900 per month plus utilities July- October (four-month lease) - $3500 per month plus utilities December - $6900 per month plus utilities January, February, and March- $8900 per month plus utilities April- $7900 per month plus utilities May ...

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Property Type

Siesta Key Bungalow

"Perfect location to enjoy Siesta Key – wonderful hosts – stay here!"

Choose this home for its fantastic location, hosts and amenities - easy walk to the beach or downtown Siesta Key, but feels miles away from the crowds in its tropical setting.The home was perfect for ...

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$750

avg/night

View Details

Key Amenities

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

About this property

Create memories with friends and family at this unique, and spacious property only 10 minutes from Siesta Key Beach.. It is perfect for large groups or reunions as this house includes 3 separate living spaces and has a total of 13 beds. Right behind the main house, not only will you find a fun area to ...

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Property Type

Siesta Key Estate

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2 BR | 2 BA | Sleeps 6 | Quick View

$123

avg/night

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Key Amenities

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

About this property

Two bedroom, two bath condo available for minimum monthly rental. Beautiful, quiet location, beach front property and pool available.

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Property Type

Siesta Key Condo

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2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 850 feet to Crescent Beach

$202

avg/night

View Details

Key Amenities

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

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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Property Type

Siesta Key Condo

"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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Key Amenities

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

About this property

Relax and unwind in our spacious, sun-filled villa that is situated in an idyllic private neighborhood. Enjoy quiet surroundings, perfectly situated within steps to all that Siesta Key has to offer. The open-concept villa boasts an incredible recently renovated chef’s kitchen equipped with high-end ...

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Property Type

Siesta Key Villa

"Fantastic"

We had a wonderful week staying at this place. Definitely as advertised. Spacious, well-equipped and very clean. You can certainly travel light when you stay here. The neighborhood is quiet with a secluded ...

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1 BR | 1 BA | Sleeps 3 | Quick View

10

Distance to beach: 0.5 miles to Siesta Key Main Beach

$202

avg/night

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Key Amenities

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

About this property

Sweet Siesta Key Condo, Spacious and Quiet One Bedroom with 2 Queen beds. Please note that RATES ALREADY INCLUDE 13% TAXES. Condo is walking distance to Siesta Key Main Beach, and a nice 0.9 mile sidewalk walk (or bike or free trolley) to Siesta Key Village. Six new Pickleball courts and 2 Tennis Courts ...

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Property Type

Siesta Key Condo

"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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Key Amenities

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

About this property

Beautiful house on Siesta Key with private pool and generous space. 15 min walk to the beach! This charming 3-bedroom, 2-bathroom private home is located in discreet residential neighborhood, on the beautiful Siesta Key island. It offers a large fenced outdoor area, with a private pool, plenty of parking ...

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Property Type

Siesta Key House

"great location to the Village and beach"

A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit ...

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Key Amenities

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

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! This unit can be combined with the adjoining unit for 8 bedrooms total. There is a wonderful outdoor living space, living room, dining area, kitchen, office as well as laundry ...

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Property Type

Siesta Key Condo

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Studio | 1 BA | Sleeps 2 | Quick View

4

Distance to beach: 0.3 miles to Siesta Key Beach access 10

$200

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only*******SPECIAL - March and April 2024 - $200 per night plus utilities - 14 night minimum****May - November (seven-month lease) - $1750 per month plus utilities May - November (three-month lease) - $2500 per month plus utilities December - $3900 per month plus utilities January, ...

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Property Type

Siesta Key Studio

"Garden Terrace"

Fantastic location and great (very responsive) hosts! We will be back at some point for sure- thanks!

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2 BR | 2 BA | Sleeps 6 | Quick View

3

$143

avg/night

View Details

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

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

Distance to beach: 1 miles to Turtle Beach

$385

avg/night

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Key Amenities

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

About this property

New Listing Siesta Key, Florida !!100% 5 Star reviews on AirBnB and VRBO, save fees by booking direct through owner on this site. Discounts for multiple monthly stays.Available June, August, September and October and December 15, 2024 - January 18, 2025 Not available January 18 - May 16, 2025Hibiscus ...

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Property Type

Siesta Key House

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Key Amenities

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

About this property

SIESTA KEY.GETAWAY Experience a luxury condo with a view. Located on the world renowned Crescent Beach at Siesta Key. Gulf and Bay Club is a 32 acre resort community with exceptional beach access, top notch amenities and amazing sunsets. 6 pickle ball courts. 5 hard court, 1 clay tennis courts. Gym. ...

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Property Type

Siesta Key Condo

"Perfect Stay for Relaxation and Fun!"

Our family had the pleasure of staying at this Gulf and Bay rental on more than one occasion. The condo is a hidden gem with a spectacular view, and just steps away from the beach. We could not have asked ...

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2 BR | 2 BA | Sleeps 6 | Quick View

6

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$130

avg/night

View Details

Key Amenities

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

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities 50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

"A Great Home Away from Home"

I loved my two months at Blue Lagoon. It has a great location, near the beach and the village. Palm Island is a great neighborhood, a secluded enclave within Siesta Key. I got to know a lot of my neighbors ...

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3 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.7 miles to Siesta Key Beach

Key Amenities

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

About this property

Hard to find home near #1 Siesta Key Beach and Village with all the amenities. The space Welcome to island life!Luxurious 3 bed/2 bath with spectacular water view and walking distance to the village restaurants, shopping, and #1 beach in America!Enjoy your heated pool, hot tub, fire pit, and ...

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Property Type

Siesta Key House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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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Property Type

Siesta Key Condo

"Wonderful!"

This condo is perfect. Comfortable lanai with an excellent view of the intercoastal. Well appointed home (Best one we have ever stayed in). Everything in the condo was organzied and easy to find. Walk ...

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2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 250 feet to Crescent Beach

$346

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Direct-with-Owner Rentals: Siesta Breakers #603 offers "All-In Price" 15% to 30% Discounted Rental Rates from $1,958 to $3,708 /Wk Depending on the Season ($150 departure cleaning extra - $400.00 refundable security deposit required) & SAVINGS from $420 to $913 /Wk from the listed Siesta ...

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Property Type

Siesta Key Condo

"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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Key Amenities

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

About this property

This condo is a corner unit with one screened lanai--and two outdoor patios. One patio with 3 steps down to the grass. New porcelain tile throughout, new kitchen with Kraft Maid wood cabinets, granite counters, new stainless steel appliances, new sink and new tile back splash. Besides the 2 bedrooms, ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 3 | Quick View

11

Distance to beach: 0.5 miles to Siesta Key Main Beach

$90

avg/night

View Details

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

"Absolutely gorgeous property"

Absolutely gorgeous property. The grounds and the property were kept beautifully. All of the amenities that were promised, were there. Being so close to the beach was a plus. There was no need to rent a ...

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3 BR | 3 BA | Sleeps 7 | Quick View

6

Distance to beach: 300 feet to Siesta Beach

$718

avg/night

View Details

Key Amenities

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

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes ...

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Property Type

Siesta Key House

"Beautiful home"

Just as pictured. Clean and comfortable. Beds were great. Nice patio and easy access to beach.owner easy to work with.

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2 BR | 2 BA | Sleeps 4 | Quick View

$195

avg/night

View Details

Key Amenities

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

About this property

Home away from home.... I enjoy my coffee and cocktails at waterfront lanai and when I travel, I would love someone to enjoy it as well. I live in this condo, therefore, this unit has everything you may need and more. Boating, fishing, paddle boarding, kayaking, biking to Siesta Key Beach or free trolley ...

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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

Vacation rental close to the # 1 beach in the USA - 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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Property Type

Siesta Key Apartment

"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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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Welcome to Siesta Key Paradise!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 on Blind Pass Lagoon. From the ...

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Property Type

Siesta Key Condo

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