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Siesta Key Vacation Rentals

(206 rentals)
Siesta Key Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 20 yards to Crescent Beach, Siesta Key

Key Amenities

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

About this property

Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean...

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Featured review

"Vacation"

Nice to deal with the rent of the property , I will book again .Very easy and simple self explanation

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$325
avg per night
Siesta Key Estate
Sleeps 20, 6 bedrooms, 5 bathrooms
1 review

Distance to beach: 4 miles to Siesta Key Beach

Key Amenities

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

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 separate living spaces and has a total of 13 beds. Right behind the main house, you will find a fun area to relax, play...

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Featured review

"A perfect vacation!"

This is a wonderful 5 plus star accommodation! The location is perfect, so convenient to the beach and so many things to do. The house is stocked with everything you need and more. Michael is an excellent...

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$757
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
53 reviews

Key Amenities

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

About this property

Welcome to your little piece of paradise on Siesta Key—an oceanfront condo where the view is the experience.This fully renovated 2-bedroom, 2-bath unit offers direct, unobstructed Gulf views from the living room, kitchen, master bedroom, and lanai. There are no angled views or buildings in the...

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Featured review

"Paradise!"

Great condo, great location, so much to do. Kevin was great to work with as well. We will be back… paradise!

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$453
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - UpscaleLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos...

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Featured review

"GREAT!!"

These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.

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$258
avg per night
Siesta Key Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

***Pool will be out of service October 26th through November 20th. 20% discount will apply*** Escape to paradise in this updated 2 bedroom/2 bath villa at Polynesian Gardens on Siesta Key! Featuring an updated kitchen, tile floors and washer/dryer in unit. Enjoy three TVs and a private patio accessible...

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$154
avg per night

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Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
85 reviews

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

Key Amenities

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

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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Featured review

"Test"

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$300
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 100 feet to Crescent Beach

Key Amenities

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

About this property

Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date...

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Featured review

"Siesta Key"

The area: The general area of the condo was a fun place to visit. Plenty of stores within walking distance (just across the street). More than ample restaurants from which to choose. If you are heading...

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$392
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 100 feet to On-site Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

One of the best locations at Fisherman's Cove, condo B-101 has a sandy beach area out our back lanai door and the community swimming pool six steps from our front door!As a result of the hurricane that impacted Siesta Key in 2024, our condo was entirely rebuilt from the stud walls in! Everything...

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$322
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - UpscaleLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLFisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos...

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Featured review

"Wonderful"

Clean update lite filled condo close to everything All appliances work baths were clean and beds comfortable Would definitely return.

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$258
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"Beautiful Bayside Condo"

This is a beautiful condo in Bayside Club resort. A gated community. Well cared for. This condo is just 30 feet from one of the pools, tennis courts and pickle ball courts. It’s a short walk to...

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

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FLCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront...

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$277
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Featured review

"Great location!"

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

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$172
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLFisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos...

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Featured review

"Beautifully renovated beach condo"

The condo contained anything and everything need to have a wonderful vacation. The view of the ocean was spectacular.

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$258
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This stunning, fully remodeled 2-bedroom, 2-bathroom Siesta Key condo offers the ultimate beachfront escape. Located on the serene south end of Siesta Key in Fisherman’s Cove, the condo faces the Gulf of Mexico and is less than100 feet from the water. Enjoy beautiful tile flooring, a gourmet kitchen...

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Featured review

"Relaxing vacation Stay for a Family of 4"

The view was amazing! If you have a fisherman in your family, this is the perfect location. The place was spotless and stocked with just about every beach toy and amenity you could need. It was such a relaxing...

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$306
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 250 feet to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Featured review

"Lovely"

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

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$323
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the world...

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Featured review

"good place"

Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate

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$294
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat DocksLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLFisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the...

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Featured review

"First visit to Siesta Key"

Great location on Turtle Beach, quieter and less busy than Siesta Key Beach. Great accommodations direct access to beach with boat slip out back to get out onto Sarasota bay. Nicely equipped condo, although...

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$258
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 3 bathrooms
4 reviews

Key Amenities

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

About this property

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

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Featured review

"Siesta Key home"

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

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$295
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

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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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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$311
avg per night
Siesta Key Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLFisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is...

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$296
avg per night
New
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is the perfect location on Siesta Keywhere by day you can walk to, and enjoy, the sun and beach, as well as children’s playground, volleyball, tennis and pickle ball courts. Walk or drive one mile to shopping and dining in nearby Siesta Village. Then, retreat and relax with great evening views...

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$149
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1 bathroom
9 reviews

Distance to beach: 150 yards to Crescent Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. New hurricane windows and door installed in 2024. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and a great...

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Featured review

"Cancelled"

Due to Helena, our condo was cancelled. Would have loved to be there but understand why we couldn't. Best to the owners as they recover. I am giving 5 stars because this was not the fault of the owner.

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$274
avg per night
Siesta Key Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building...

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$296
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Siesta Key

Key Amenities

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

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

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living....

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Featured review

"March Getaway!"

Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.

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$145
avg per night
Special Offer
Siesta Key Condo
Sleeps 4, 2 bedrooms, 1.5 bathrooms
38 reviews

Distance to beach: 200 yards to Crescent Siesta Key Beach

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Paradise at Midnight Cove 1 Siesta Key, FloridaLocated on consistently top-ranked Siesta Key Beach, our beautifully remodeled bayside condo at Midnight Cove 1 offers the perfect blend of luxury, comfort, and island charm for your next tropical getaway.Nestled within a lush, gated community...

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Featured review

"BEAUTIFUL CONDO!"

Sandy's condo is AMAZING! Clean, well furnished with very comfortable beds. Location is awesome and Sandy was very nice, and easy to work with! I rate it 6 out of 5 stars!

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$196
avg per night
New
Siesta Key Villa
Sleeps 5, 2 bedrooms, 2 bathrooms

Distance to beach: 200 yards to Crescent Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to your ultimate Florida getaway! Nestled on the exclusive, world-renowned shores of Siesta Key, this beautiful two bedroom, two bathroom villa offers a rare and coveted vacation experience.Designed with the quintessential coastal lifestyle in mind, this fully furnished villa pairs the comforts...

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$273
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

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

About this property

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

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Featured review

"Gorgeous oasis!"

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

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$300
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 100 yards to Siesta Key private area of beach

Key Amenities

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

About this property

This updated Villa is on the beach side of Siesta Key, with private beach!!! It does not get better than this!! Fully renovated private villa on beachside. In 1 to 2 mins you can have your feet in the sand. Parking directly in front of villa.There is an amazing huge heated pool,, one of the biggest...

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Featured review

"Fantastic vacation, great rental!!"

Highly recommend!! Property was very clean, interior is updated; we had a very comfortable stay. Fully stocked with towels and essential kitchen cookware. Ruth was great to work with, very responsive and...

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$307
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
12 reviews

Key Amenities

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

About this property

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

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Featured review

"Vacation 2026"

Carrie was very informative the condo was so nice and cozy. Loved that it is right on the beach and close to restaurants and attractions. Already booked for 2027 before I left from vacation this year. I...

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$256
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 0.1 miles to Siesta Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

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

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Featured review

"perfection!"

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

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$263
avg per night
Siesta Key Apartment
Sleeps 2, 1 bedroom, 1 bathroom
27 reviews

Key Amenities

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

About this property

We are a small family owned resort on Siesta Key offering daily rentals Villa 4 is newly renovated Featuring 1 King bedroom, Large shower in bathroom, Large Smart TV in the Living Room, Sofa and Table and Chairs. A/C, Kitchenette with Fridge Freezer, Pop Up Toaster. Coffee Maker, K Cup, Single...

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$192
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 5 feet to Crescent Beach

Key Amenities

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

About this property

FULL GULF FRONT- Cathy's Crescent Condo-Beautiful turnkey 2nd floor condominium located on the pristine beaches of Siesta Key, FL. Voted the finest sand in the world. It doesn't get any better than this! This condominium is Full Gulf Front. You can view the water/beach while lying in bed from...

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Featured review

"Wonderful Views and Condo"

Absolutely beautiful view from every room. Wonderful sunsets every night and a few steps from the beach. Kathy is a great hostess and was very responsive to all of our questions. We are already planning...

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$323
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
52 reviews

Key Amenities

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

About this property

If you are looking for elegance, A108 is for you. If you are a sophisticated traveler and can appreciate how lovely this condominium is (as the owner spared no expense in remodeling this Gulf-front first floor vacation rental) then make your reservation now! You will walk out the lanai door directly onto...

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Featured review

"Outstanding!"

I wish there were more stars we could give! There aren’t enough adjectives in the dictionary to describe 108A. Immaculate beauty. Dina, Russ, and Rhonda, THANK YOU for your hospitality!

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$322
avg per night
Siesta Key Townhome
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 600 yards to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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Featured review

"Great Stay"

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

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$232
avg per night
Siesta Key House
Sleeps 8, 4 bedrooms, 2.5 bathrooms
11 reviews

Key Amenities

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

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened...

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Featured review

"Amazing!"

Our stay at Aloha Kai was amazing! The unit was spacious, clean and beautifully decorated. Plenty of space for our family of six, all adults. The outside space exceeding my expectations. Plenty of seating...

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$701
avg per night
Siesta Key Townhome
Sleeps 6, 3 bedrooms, 3 bathrooms
14 reviews

Distance to beach: 0.3 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Discover the ultimate Siesta Key getaway with this beautifully appointed, smoke free, 3-bedroom Townhouse, perfectly situated just 300 steps from the world-famous Crescent Beach. Enjoy the best of both worlds with Turtle Beach only 2.4 miles away, offering endless opportunities for seaside relaxation...

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Featured review

"Great location!!!"

The condo was great for our stay in Crescent beach for the month. It has everything you need to enjoy your stay at the beach. From beach chairs,bikes,umbrella's, towels and so much more. The pool was very...

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$375
avg per night
Siesta Key House
Sleeps 12, 4 bedrooms, 3 bathrooms
7 reviews

Key Amenities

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

About this property

Key Differentiators & Amenities•7 properties away to step onto the access of Siesta Key Beach (#1 beach in the US) •Ample parking for RV, boat, and multiple vehicles •EV charging station onsite •Private saltwater pool (fenced backyard) •Pet-friendly: beds, crates,...

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$624
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront...

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Featured review

"Beach and ocean waves"

The condo was super nice. The master bedroom mattress was amazing for a rental. So often I feel like they are hard as rocks but this one wasn’t. The second bedroom had similar mattress but they were not...

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$277
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 20 yards to Crescent Beach, Siesta Key

Key Amenities

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

About this property

Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean...

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$246
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
21 reviews

Key Amenities

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

About this property

Your private Siesta Beach escape! Walk or bike to sand, unwind in the heated saltwater pool or Sauna and bring your furry friends along!Key Differentiators & AmenitiesSought-after Siesta Key Family & Pet friendly location—easy access to the beach, village, shops, restaurants, coffee...

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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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$436
avg per night
Siesta Key Villa
Sleeps 8, 4 bedrooms, 2 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

NEWLY RENOVATED IN 2023!!VERY SPACIOUS 4 BEDROOM 2 BATHROOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS,VILLA SLEEPS 8, 1 KING, 1 QUEEN,...

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Featured review

"Polynesian Gardens Villa"

This 4 bed 2 bath villa was perfect for our family vacation! It's spacious with towels, chairs and wagon for the beach! Ali and her team are great!

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$212
avg per night
Siesta Key Apartment
Sleeps 2, 1 bedroom, 1 bathroom
14 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Experience the delightful simplicity of a tranquil beach getaway at Paisley's Casita. Nestled just a 7-property walk away from the serene vibes of Siesta Key Beach, this enchanting Studio Casita exudes similar charm to a hotel room whilst offering all the essential amenities for an undisturbed sojourn....

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Featured review

"Extra room needed for family"

We rented this property for 5 nights for 2 people. The property was private via surrounded by a fence,provided bikes for transportation, and had an inviting back yard area with 2 chairs and grill. We were...

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$115
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

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

Key Amenities

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

About this property

Our gorgeous condo is surrounded by water with the Gulf of Mexico on one side and Blind Pass Lagoon on the other side and Sarasota Bay within kayak range! Such a unique setting, sitting at the southern and most private end of Siesta Key. B203 is on the second floor and the views are stunning! Our community...

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Featured review

"Wonderful just like home!"

This condo is beautiful! You will not need to bring anything but your swimsuit! Very well equipped n very clean! Best beach home ever! Plenty of space and so up to date on kitchen n bathroom! I could not...

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$302
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

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

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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Featured review

"Amazing Stay"

My family and I had the most amazing stay in Don & Elaine’s condo! We have been coming to Siesta Key for 6 years and this was our favorite room- best location and best view ever! We look forward to returning....

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$353
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

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

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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Featured review

"Spring Break 2026"

My daughter and I went down and enjoyed the place. The convenience to get to the beach was great and it was such a big area!! Loved walking around the key!! Love Siesta Key and this was a fabulous place...

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$421
avg per night
Siesta Key House
Sleeps 14, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Casa De Mayo — your private waterfront retreat in the Village of Siesta Key within walking distance to the beach. Perfectly situated just a stroll from Siesta Village and the world-famous powder-soft sands of Siesta Beach, this stunning home offers the best of both worlds: vibrant island...

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$782
avg per night
Siesta Key Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building...

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$296
avg per night
New
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key - Ground Floor Gulf-Front Retreat - 2 BR – Free Boat Docks Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest...

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$258
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
52 reviews

Key Amenities

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

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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Featured review

"Absolutely perfect!"

The owners make your arrival amazing. You have to experience it to know. The view is breathtaking. Both the back of the property and the front have spectacular views. The property is perfectly equipped...

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$270
avg per night
Full map
Map

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

FAQ

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

There are 206 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to apartment rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Siesta Key?

There are vacation rentals available in Siesta Key for as low as $100 per night with an average price per night of $260.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 99 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 51 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!