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Siesta Key Vacation Rentals

(188 rentals)
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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$254
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
8 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"Rental review"

Great place, updated and clean with everything you need! Beach supplies came in handy for trips to the beach. The pool was a great place to go at the end of the day! The office personal were very pleasant...

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$150
avg per night
Siesta Key House
Sleeps 7, 3 bedrooms, 3.5 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Our 3 bedroom, 3 1/2 bath beach house is located on Siesta Key and is on the gulf side of Beach Road. Our home is a standalone unit on 3 levels with 2 decks, a ground level patio, with a on e car garage. We are directly on Crescent Beach with gulf views from inside and outside and have a private access...

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Featured review

"Siesta Key Rental"

Our family had the best vacation together at our rental home on Siesta Key. Carole is an awesome landlord providing many amenities and comforts that made our stay feel like home. Will definitely return.

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$366
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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$297
avg per night
New
Siesta Key Condo
Sleeps 5, 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

Experience true Gulf-front living at Fisherman’s Cove B103, a beautifully renovated beachfront condo located at 9000 Blind Pass Rd, Siesta Key, Florida.The virtual tour was taken in 2021. In 2024 we experienced the hurricanes which changed the beach beyond the rocks that you see in our current...

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$251
avg per night

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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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$270
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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$290
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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$262
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 1.5 bathrooms
6 reviews

Distance to beach: 200 yards to Siesta Key/ Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our vacation home is just steps away from the #1 rated beach in the USA - Siesta Key beach. It is unit B07 in the Casa Blanca resort located on the GULFSIDE (or Beach side) of the island.It is a comfortable villa with a master bedroom, guest bedroom, living room, kitchen with dining area, and a...

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Featured review

"Our Casa Blanca experience"

This was our second vacation in as many years at Casa Blanca. Both times we selected the same unit number and both times we were simply delighted with the experience. Everything exceeded our expectations....

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$284
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
10 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

"A very special place"

This is a magical spot on the beach! I have been coming for years and I just love it. It is a fully equipped unit that is missing nothing. Carrie is an exceptional host. If there is anything missing or...

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$251
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 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. (Updated pics coming soon) There is an amazing huge pool,,...

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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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$320
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

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 This gorgeous Siesta Key luxury beach view condo is directly on world famous Crescent Beach located mid-Key,...

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$290
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
30 reviews

Distance to beach: 0.1 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Skip the parking hassle — you’re just steps from Siesta Key Beach, consistently ranked #1 in the U.S.This newly upgraded 2-bedroom, 2-bath condo is perfectly located directly across from the beach and minutes from Siesta Key Village. Walk, bike, or hop on the free trolley to reach top...

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Featured review

"Condo at siesta key"

Rented our condo from Christina it was everything she said it was. Condo very nice beds super comfy had a great time there would rent again.

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$150
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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$131
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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$254
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

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

"Paradise"

Carrie: You are the only person I will write a review for. You are an awesome landlady, and I think you know how much I value your place. I have now been there five out of the last six years, and the...

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$280
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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$135
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: -100.0 feet to Crescent Beach -- we are located on the beach

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Sea Crest on Siesta Key is a small 40-unit condominium complex at 1129 Seaside Drive consisting primarily of one-bedroom units with separate bedroom, one efficiency, and one two-bedroom, two-bathroom unit. A true old style Floridan resort. Enjoy our one bedroom condo just a few steps to our private...

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Featured review

"Great family vacation"

I was supposed be there Oct 1 to 29th, but hurricane Ian had other plans for me, Jeffrey the manager was very acommodating in making all the necessary changes to make my stay wonderfull. I ended going the...

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$231
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
44 reviews

Key Amenities

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

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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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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$288
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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$405
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
14 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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$479
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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$297
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

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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$284
avg per night
New
Siesta Key Apartment
Sleeps 2, 1 bedroom, 1 bathroom
5 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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$115
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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$254
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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$349
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
13 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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$420
avg per night
Siesta Key Condo
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 0.1 miles to Siesta Key

Key Amenities

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

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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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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$1,000
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...

View all property information

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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$254
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
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

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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$308
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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$289
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 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 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 Administrative Fee: 3.00% Last...

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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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$329
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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$178
avg per night
Siesta Key Condo
Sleeps 8, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the gorgeous 2BR 3Bath beachfront townhouse nestled in the tranquil complex on Siesta Key, FL. Escape the big-city crowds and enjoy the lovely ambiance from the patio while being just a few steps from the pristine sandy beach, swimming pool, local restaurants, shops, and attractions. 2 Comfortable...

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$465
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 0.1 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This amazing condo offers a Gourmet Kitchen and island. Granite counter tops, high ceilings and stainless steel appliances (including super quiet Bosch dishwasher and French door refrigerator with two ice-makers).Removed and replaced all forty year old Duct-work with brand new Flex Duct-work for improved...

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$297
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
47 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

"Wonderful Location at the end of Siesta Key"

You cannot get any closer to the water! You have the gulf in front of you and an inlet behind you. Views were wonderful. Unit was very clean and well stocked with beach items. We loved the Trolley which...

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$260
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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$195
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

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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$220
avg per night
Siesta Key House
Sleeps 12, 4 bedrooms, 3 bathrooms
5 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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$656
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 I 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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$182
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 queen size bedrooms, 2 bathroom , second floor end unit, adjacent from the pool, available for rent. Laundry availalbe on the first floor of the building. short walk to the ocean. Quiet and private space to relax and enjoy.

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$171
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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$308
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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$719
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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$232
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

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. A306 is on the third floor and the views are stunning! Our community...

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Featured review

"AMAZING VIEW!!! :)"

Wow!!! Where do I start? I knew we had booked the right condo when we rounded the corner and could see the Gulf. This was a present for my daughter's senior trip / 18th birthday and it did not disappoint....

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$284
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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$349
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 188 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 $67 per night with an average price per night of $251.

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 88 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 54 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!