Siesta Key Rentals by Owner

(82 rentals)
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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
2 reviews

$295

avg/night

$295
avg per night
View Details

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

Featured review

"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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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
7 reviews

$381

avg/night

$381
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"perfect spot"

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

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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
8 reviews

$431

avg/night

$431
avg per night
View Details

Key Amenities

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

About this property

Take it easy at this mid-century modern peaceful Siesta Key Beach family & pet friendly getaway. 3 BD, 2 BA’s & 2 outdoor showers to wash off the sand after beach fun. Don’t forget to bring Fido! Hang out by the fire pit in the evenings while you grill out taking in the ocean air with ...

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Property Type

Siesta Key House

Featured review

"Paradise"

The home on Siesta Key is totally amazing in every aspect. The completely updated modern architecture combined with the lush tropical landscape make this an excellent choice to relax and experience ...

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

$316

avg/night

$316
avg per night
View Details

Key Amenities

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

About this property

Condo, 2 Bedrooms, 2 Baths, Sleep Sofa (Sleeps 4-6) If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. This is the ‘Best Location’ on ‘Crescent Beach.’ Experience ...

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Property Type

Siesta Key Condo

Featured review

"Wonderfully Relaxing"

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

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
9 reviews

$307

avg/night

$307
avg per night
View Details

Key Amenities

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

About this property

If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the ...

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Property Type

Siesta Key Condo

Featured review

"Beware of Horrible Communication"

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

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
2 reviews

Distance to beach: 850 feet to Crescent Beach

$201

avg/night

$201
avg per 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

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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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
8 reviews

Distance to beach: 0.2 miles to Siesta Key

$278

avg/night

$278
avg per night
View Details

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

Featured review

"Great place!"

This was our first time back to Siesta Key in 20 years and we loved this condo! The location is right between the two villages, so super easy to grab a trolly to dine or shop. The beach is a pretty short ...

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
47 reviews

$347

avg/night

$347
avg per night
View Details

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

Featured review

"Little piece of heaven"

I can't say enough about this property absolutely heaven out your front door is a beautiful Bay with manatees playing in it pretty much every day we were able to be there!! out the back door you're about ...

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Siesta Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
3 reviews

Distance to beach: 0.4 miles to Siesta Key Beach

$550

avg/night

$550
avg per night
View Details

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

Featured review

"Excellent"

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

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
78 reviews

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

$333

avg/night

$333
avg per night
View Details

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

Featured review

"PERFECT BEACH CONDO"

This condo was amazing! The hosts were very polite and responsive. The condo was clean and well-equipped with everything we needed, including a beach wagon, chairs, sand toys, umbrellas, a boogie board, ...

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
2 reviews

Distance to beach: 950 feet to Crescent Beach

$201

avg/night

$201
avg per night
View Details

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

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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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
44 reviews

$347

avg/night

$347
avg per 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 ...

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Property Type

Siesta Key Condo

Featured review

"You WILL NOT be disappointed with this condo!!!"

I have nothing but rave reviews of this rental - the location, the condo itself and the owners. We had an amazing time and they had anything and everything that you could want in the condo. We will definitely ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

$340

avg/night

$340
avg per night
View Details

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

Featured review

"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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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
3 reviews

$293

avg/night

$293
avg per night
View Details

Key Amenities

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

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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Property Type

Siesta Key Condo

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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Siesta Key Condo | On the beach
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 Bedrooms, 2 Bathrooms
8 reviews

$750

avg/night

$750
avg per night
View Details

Key Amenities

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

About this property

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
3 reviews

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

$196

avg/night

$196
avg per night
View Details

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

Featured review

"Siesta Sand Dollar"

We had an amazing stay at Maria's place at Siesta Harbor. Everything had just been updated and was very modern and beautiful. We would highly recommend her unit and we are looking forward to going back ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
22 reviews

Distance to beach: 0.1 miles to Siesta Key Beach

$209

avg/night

$209
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Great location, great property, and a ton of fun activities nearby!!"

The property has two rooms with their own bathrooms and it was perfect for what we needed. Choosing whether to spend time at the pool, beach across the street or playing pickleball, also across the street ...

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
8 reviews

$350

avg/night

$350
avg per night
View Details

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

Featured review

"Excellent Condo A306"

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

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
5 reviews

$347

avg/night

$347
avg per night
View Details

Key Amenities

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

About this property

This vacation rental condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims. We are excited to announce that B108 has recently been ...

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Property Type

Siesta Key Condo

Featured review

"Outstanding"

This is our third year in a row staying at Fishermans Cove. Our first year we were in a second floor condo these last two years we had ground floor and wouldn’t have it any other way. Everything is spotless, ...

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Siesta Key Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
43 reviews

$303

avg/night

$303
avg per night
View Details

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

Featured review

"Just Perfect"

Location was amazing - views spectacular, nothing separating us from the beautiful gulf. Condo - was missing nothing and needed nothing additional. Clean. Stocked. Convenient. Comfortable. Owners - ...

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Siesta Key Townhome
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
8 reviews

Distance to beach: 0.3 miles to Crescent Beach

$395

avg/night

$395
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

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

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Property Type

Siesta Key Townhome

Featured review

"Paradise!"

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

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
11 reviews

$394

avg/night

$394
avg per night
View Details

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

Featured review

"Amazing"

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

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
6 reviews

$402

avg/night

$402
avg per night
View Details

Key Amenities

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

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai. *Decorated in a "beachy motif" with granite counter tips in the kitchen ...

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Property Type

Siesta Key Condo

Featured review

"Beauty at the Beach"

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

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
7 reviews

$323

avg/night

$323
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Siesta Key Serenity"

I absolutely loved my stay. The condo was impeccable and the sunsets were gorgeous. I highly recommend this unit. The master suite was so lovely. We really enjoyed the pool, spa, and trips to the Village.

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Siesta Key House | On the beach
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2.5 Bathrooms
10 reviews

$797

avg/night

$797
avg per night
View Details

Key Amenities

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

About this property

We lucked out! Hurricane Helene did not flood our beach house except for the carport. (But the Aloha Kai area is closed for the at least one month.) Hurricane Milton damaged some soffits. A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, ...

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Property Type

Siesta Key House

Featured review

"Perfect Getaway!"

We SO enjoyed our stay there! Our stay was to celebrate a milestone birthday of our sister and we couldn't have asked for a better spot! Our main goal was to relax, catch up and enjoy the beautiful beach ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
5 reviews

$274

avg/night

$274
avg per night
View Details

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

Featured review

"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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Siesta Key Townhome
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3.5 Bathrooms
5 reviews

Distance to beach: 0.3 miles to Crescent Beach

Inquire for rates

Inquire for rates

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

6828 Midnight Pass Road is a townhouse style condo three level unit with 3 main bedrooms plus a bonus bath and laundry and bedroom on the ground floor. Each bedroom has a queen bed, and all furniture and mattresses were purchased new in 2021. New AC and duct work in 2023. Brand new exterior paint and ...

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Property Type

Siesta Key Townhome

Featured review

"Best vacation ever!!"

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

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Siesta Key House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 2 Bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Your dream vacation awaits! Your spacious and private single-level house is a perfect getaway for a peaceful and relaxing vacation. Enjoy all the comforts of home while being just a short walk away from bars, restaurants, and Siesta Key's beautiful white sand beaches. Nestled on a quiet tree-lined ...

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Property Type

Siesta Key House

Featured review

"Incredible, Comfortable Stay in an Excellent Location"

I've enjoyed three years in a row at Jonathan's wonderful Siesta Key house and hope to continue doing so for years to come. I've stayed at multiple rentals all over the country and nobody's home or hospitality ...

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Siesta Key Condo | On the beach
4 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 4.5 Bathrooms

Distance to beach: 0.3 miles to Siesta Beach

$667

avg/night

$667
avg per night
View Details

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 with dining table and lounging area, living room, dining area, ...

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Property Type

Siesta Key Condo

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Siesta Key Apartment
3 BR | 2.5 BA | Sleeps 7 | Quick View
Sleeps 7, 3 Bedrooms, 2.5 Bathrooms

$387

avg/night

$387
avg per night
View Details

Key Amenities

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

About this property

This charming Siesta Key vacation rental home offers a beautiful kitchen, dining area, living room, and outdoor patio. The property includes access to a heated pool shared between the two units in the house. Located in the heart of Siesta Key Village, it's just a 3-minute walk to the #1 beach in ...

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Property Type

Siesta Key Apartment

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Siesta Key Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
9 reviews

$243

avg/night

$243
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Just what we wanted."

Just returned from a week in Karen’s condo. Her place is perfect. The balcony and view were wonderful. Sitting and looking at the beach was so relaxing. The condo was great. Gave you a beach feeling. ...

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
1 review

$373

avg/night

$373
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Beautiful Condo!"

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

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
31 reviews
owner special
Owner special: February dates available, we had no damage from the hurricane!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$241

avg/night

$241
avg per night
Owner special:
February dates available, we had no damage from the hurricane!

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Great place!"

Great place to stay! Has everything you need for a great beach stay. The condo was clean, decorated nicely, and offered beach supplies. It was only a short walk to the beach as well. The host was great ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
11 reviews

Distance to beach: 0.2 miles to Siesta Key Beach

$269

avg/night

$269
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Gulf and Bay Bayside Unit #1344 D"

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

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Siesta Key House
Studio | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 0 Bedrooms, 2 Bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

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

About this property

Comfortable and peaceful home with private saltwater pool and hot tub, 1.4 miles from the beach; 1 mile to the village. I have beach gear. Plenty of chairs, an umbrella, towels and coolers. Beautiful private back yard with grill and smoker in quiet neighborhood. Very comfortable and peaceful retreat. ...

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Property Type

Siesta Key House

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
13 reviews

Distance to beach: 0.0 miles to Siesta Key Public Beach

$361

avg/night

$361
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

Featured review

"Siesta Key get away"

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

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2.5 Bathrooms

$475

avg/night

$475
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Siesta Key Condo

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Siesta Key Villa | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
1 review

$308

avg/night

$308
avg per night
View Details

Key Amenities

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

About this property

This updated Villa is on the beach side of Siesta Key, with private beach!!! Newly renovated private villa! Beautiful brand new kitchen with quartz countertops and stainless steel appliances. All new flooring through out and newly decorated! Be one of the first guests in this newly renovated clean ...

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Property Type

Siesta Key Villa

Featured review

"Highly Recommend!"

I would highly recommend renting through Ruth. Her villa was in the perfect location, with great beach access and it was newly renovated! Ruth was easily accessible and answered every question I had. The ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$244

avg/night

$244
avg per night
View Details

Key Amenities

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

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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Property Type

Siesta Key Condo

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
6 reviews

$336

avg/night

$336
avg per night
View Details

Key Amenities

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

About this property

This 5th floor two bedroom, two bath condo is totally and completely renovated. Be one of the first guests to stay in this beautifully renovated condo. New tile throughout. There are two bedroom suites with private baths. Each bedroom has new slider doors that open to screened in lanai with beautiful ...

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Property Type

Siesta Key Condo

Featured review

"Relaxing getaway"

We had a really nice week in this condo just steps to the beach. The powdery white sand never gets hot.The condo has all of the essentials and more. Very comfortable. And there’s a nice pool if want to ...

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Siesta Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$429

avg/night

$429
avg per night
View Details

Key Amenities

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

About this property

Very private - empty lot across the canal and fenced in. Walk to the islands best restaurants, bars, shops and ice cream parlors. The beach is a short stroll (8 min), use free golf cart taxi or ride provided bikes with tow behind cart! Siesta is well known for its #1 beach in the USA!

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Property Type

Siesta Key House

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Siesta Key Condo | On the beach
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
5 reviews

Distance to beach: 0.1 miles to Siesta Key

Key Amenities

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

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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Property Type

Siesta Key Condo

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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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
6 reviews

Distance to beach: 100 yards to Crescent Beach

$260

avg/night

$260
avg per night
View Details

Key Amenities

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

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a Lazyboy queen memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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Property Type

Siesta Key Condo

Featured review

"Sea Crest #26"

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

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Siesta Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
3 reviews

$314

avg/night

$314
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

Featured review

"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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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$243

avg/night

$243
avg per night
View Details

Key Amenities

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

About this property

Our condominium is in the beautiful, gated complex of Gulf and Bay Club on Siesta key Beach, one of the top beaches in America! It has a very large kitchen, 2 King bedrooms and 2 bathrooms. It has been updated with a new King bed and gel mattress, updated bathrooms, new kitchen quartz counter tops and ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
8 reviews

Distance to beach: 1 miles to Crescent Beach

$276

avg/night

$276
avg per night
View Details

Key Amenities

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

About this property

NEW ON SIESTA KEY RENTAL!! Completely renovated First floor Condo. Two bedrooms 2 baths - very close to the pool. Master bedroom has a King bed with on-suite bathroom and walk-in closet. Second bedroom has a Queen bed and twin bunk beds. Fully equipped kitchen with state-of-the art appliances. ...

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Property Type

Siesta Key Condo

Featured review

"Can't say enough good things!!!"

This condo was phenomenal! It was beautiful, extremely clean, had everything you would need if you cooked a lot, plenty of beach equipment, even a collapsible wagon for the beach. It was great having the ...

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
7 reviews

$163

avg/night

$163
avg per night
View Details

Key Amenities

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

About this property

Our little piece of paradise is a one bedroom condominium ideal for couples or young families. We are located at 73 Avenida Messina in unit #7 on the ground floor of the Gulf Holiday Apartments. We are 300 ft. from the Gulf of Mexico and about a five minute walk from the village - known for its shops, ...

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Property Type

Siesta Key Condo

Featured review

"Condo #6"

We enjoyed staying in Condo #6 for two nights before Hurricane Helene arrived. We evacuated and weren’t able to return. We hope to stay here again in the future. We have stayed in these condos for ...

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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$365

avg/night

$365
avg per night
View Details

Key Amenities

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

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 sea shells and shark’s ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
7 reviews

Distance to beach: 200 feet to Siesta Key Public Beach

$330

avg/night

$330
avg per night
View Details

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

Featured review

"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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Siesta Key Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

$301

avg/night

$301
avg per night
View Details

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

Featured review

"CASARINA on Siesta Key Beach-#1 Beach, Place to Visit, Hosts"

To start off with Chris and Jeannie are the best hosts to deal with. Easy going, prompt if anything is needed! They share their lovely home with us vacation lovers visiting literally the #1 Beach-Siesta ...

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Siesta Key Vacation Rentals