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Siesta Key Vacation Rentals

(197 rentals)
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 just 100 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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$279
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 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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$280
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
51 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

"Fabulous seafront condo"

We had a wonderful vacation in this beautiful condo and will certainly look to return at some point in the future.The location is stunning with direct access to the beach and uninterrupted views of...

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$304
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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$239
avg per night

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Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 0.3 miles to Siesta

Key Amenities

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

About this property

Enjoy resort amenities at the Harbor Towers tennis and Yacht club in Siesta key. The building has completed a $13 million dollar structural and cosmetic renovation and is a beautiful building highlighting Siesta key and Midnight Pass. This condo offers the option to play tennis, swim at the pool exercise...

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$151
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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$171
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
17 reviews

Key Amenities

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

About this property

Complete remodel 2026! The Gulf of Mexico is only 100 ft. from your private sand beach and lanai entrance. Listen to the surf from your master bedroom. Enjoy dining on the lanai while watching the sunset. During the day you can see dolphins, kite boarding and sea birds. This unit has all the comforts...

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Featured review

"Absolutely perfect paradise!!!"

The condo was pristine and spotless! The furniture and appliances were all brand new and very comfortable especially the reclining sofa and the mattresses and pillows were also very nice. The washer and...

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$235
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 400 feet to Siesta Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Prime location, being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor...

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Featured review

"Fantastic place"

This home is absolutely beautiful and spotless! Has every amenity you could want and is so close to the beach! Working with the host was very easy and very accommodating. You would totally enjoy this stay,...

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$508
avg per night
New
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

Welcome to Beachfront Serenity at Fisherman’s Cove B204, a beautifully updated Gulf-front condo located at 9000 Blind Pass Road, Siesta Key, Florida. This rare coastal retreat offers one of the most unique locations on the island—Gulf views in the front and Sarasota Bay waters just steps from...

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$238
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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$278
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 House
Sleeps 6, 3 bedrooms, 2 bathrooms
18 reviews

Key Amenities

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

About this property

Welcome to our 3 Bedroom 2 Bathroom Siesta Key Beach House. Full kitchen. Walk to beach. We provide chairs & towels for the Beach Walk to Beach access #12 on Siesta key Lots of places to eat and drink, close by.Free WIFI Daily, Weekly rentals. Swimming Pool on site King Bed in Master...

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$408
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 I 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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$173
avg per night
Siesta Key House
Sleeps 10, 4 bedrooms, 3 bathrooms

Distance to beach: 0.6 miles to Siesta Key Beach

Key Amenities

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

About this property

Welcome to your slice of paradise on Siesta Key—where coastal charm meets everyday convenience. This beautifully maintained single-family pool home offers the perfect blend of privacy, comfort, and proximity to the island’s natural beauty. Step outside and enjoy the lush, landscaped backyard,...

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$244
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Featured review

"Truly a five star condo!"

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

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$231
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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$278
avg per night
Siesta Key Apartment
Sleeps 25, 9 bedrooms, 9 bathrooms
5 reviews

Key Amenities

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

About this property

Our seven apartment beach house is located 100 yards from the beach at Access #7 and one-block from the tropical Village of Siesta Key. Heated pool and spa along with our poolside surfboard bar and barbecue give our guests many choices to very their daily routine. Our 1st and 2nd floor above ground level...

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Featured review

"Spring Break at Midnight Cove II"

had a lot of great options that were not found on the typical rental sites. I sent multiple requests and received feedback from most of the requests that I submitted. The owner of the unit we ended up booking...

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$315
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
12 reviews

Key Amenities

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

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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Featured review

"Great view!"

Great family vacation spot with great views and nice condo. Crescent arms staff are all very friendly and helpful.

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$421
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, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront...

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$262
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
20 reviews

Key Amenities

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

About this property

This outstanding condo, A203, is on the second floor, accessible using the elevator or outside stairwell and is completely renovated with modern tile flooring throughout, updated kitchen and baths, and comfortable furniture! The kitchen has granite counter tops with tiled back splash, and modern appliances...

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Featured review

"Siesta Key Vaca"

We are lifetime residents in the area & haven't been to Turtle Beach/South Sieta Key for years. Fisherman's Cove was a great find for a week stay. Our unit was renovated in a fun beachy theme with nice...

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$278
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 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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$334
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

This 5th floor two bedroom, two bath condo is just a few steps for the private area of Siesta Key Beach!. Beach chairs and beach loungers are provided at the beach entrance. Shade in one of our Beach cabanas. Private parking under carport. Shower at the beach entrance. Wake up to amazing views on your...

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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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$300
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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$265
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Discover your own slice of paradise in this brand new 100% fully renovated 2-bedroom, 2-bathroom villa, with vaulted ceilings and an open floor plan. This villa is located in the vibrant heart of Siesta Key. This charming retreat blends modern amenities with a prime location, ensuring an unforgettable...

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$254
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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$132
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
10 reviews

Key Amenities

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

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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Featured review

"all that and a box of chocolates"

crescent royal condos was top notch condo 409 was as clean as a surgical room the view was better than I expected beach beyond perfect location perfect if your looking for a great place this is it

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$200
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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$305
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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$168
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

Key Amenities

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

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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Featured review

"Amazing vacation!!"

Carrie is amazing to work with, she has a beautiful rental and in an excellent location. You have the beach, paddle boarding and kayaking behind, this place is a bit of heaven on earth. We love it and keep...

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$258
avg per night
Siesta Key House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

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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Featured review

"Wonderful home"

We stayed here for the month of March this year. We absolutely loved the house. Everything is brand new. The lanai and spa were a bonus. One block from the village and all of the bars and shopping. Hope...

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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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$304
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This first floor colorful unit sleeps 6 and you will love the sandy beach just outside the lanai door with comfortable patio chairs. Walk past the dune to enjoy more beach and the Gulf of America. A lovely spot to watch sunsets. The unit is upgraded and comfortable for couples traveling together or with...

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Featured review

"Seista Key 2026"

Property was under reconstruction after storm last time I was there. It is now ready for rental. I intemt to travel there next week and will stay for the month.

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$238
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 30 yards to Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Bright and inviting, this popular unit has floor to ceiling sliding glass doors from the lanai, offering breathtaking third floor views. Beautiful white porcelain tile leads to new bamboo laminate flooring, which is just one of the many recent upgrades. The open kitchen has comfortable counter seating...

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Featured review

"Holmes Beach Rental"

We loved our visit and loved the condo. The views were amazing . The only compliant would be the living room furniture was not comfortable. And the kitchen could use more kitchen items. But we dealt with...

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$238
avg per night
Siesta Key Apartment
Sleeps 2, 1 bedroom, 1 bathroom
9 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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$94
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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$239
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Newly fully luxuriously decorated beach Townhouse is just a few steps from the private white sandy US #1 rated Siesta Key Beach. This 2 bedroom 2.5 bath is everything you want and more! It will exceed your expectations. Look no further Check-in time: 15:00 Check-out time: 11:00 Last Minute Discount:...

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Featured review

"BEST BEACH STAY EVER!"

We have had numerous beach stays in the area, and this one met every expectation we had! It's a bit farther from the downtown area than what we were used to, but the walk was totally doable and the free...

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$367
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

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

Key Amenities

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

About this property

This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with private beach access and overlooking its own private harbor is the perfect getaway to the #1 beach on Siesta Key in Sarasota, Florida. This unit is located near the community pool and hot tub along with guest grilling...

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Featured review

"Easy and FUN Vacation"

The booking and check in process was easy. In addition , we appreciated how fully stocked and clean the condo was. Getting around the island was simple (walking and riding the tram). Best of all, the beach...

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$139
avg per night
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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$277
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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$229
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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$238
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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$240
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 0.2 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"Mullins review"

The place was very clean. The location was perfect for beach trips and trolleys for visiting the village.

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$250
avg per night
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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$313
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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$262
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
17 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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$360
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Wake up to breathtaking views of the award-winning Siesta Key Beach from every room in this stunning, updated two-bedroom, two-bath condo. Designed for relaxation, this bright and airy retreat features an open floor plan, neutral tile, and an abundance of natural light. Step onto the screened-in lanai...

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$114
avg per night
Siesta Key House
Sleeps 12, 4 bedrooms, 3 bathrooms
6 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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$554
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 90 feet to In front of condo!

Key Amenities

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

About this property

The new owners have spared no expense in transforming this bright, inviting waterfront condo into a luxurious coastal retreat. Completely remodeled from top to bottom, the condo features new luxury flooring, solid-core six-panel doors, fresh paint, new light fixtures, ceiling fans, and beautifully rebuilt...

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$278
avg per night
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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 197 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 $68 per night with an average price per night of $239.

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 97 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 53 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!