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Siesta Key Vacation Rentals

(196 rentals)
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 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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$282
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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$265
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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$237
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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$241
avg per night

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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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$268
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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$201
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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$230
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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$507
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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$241
avg per night
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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$148
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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$279
avg per night
Siesta Key House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to paradise! Your tropical oasis awaits you in this spacious two-story home. This stunning 4 bedroom, 4.5 bath luxury home with a private heated pool is just blocks from Siesta key beach! Five star amenities include; expansive gourmet kitchen with granite counter tops, handsome wood cabinetry,...

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$241
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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$236
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1 bathroom
4 reviews

Distance to beach: 0.0 miles to Siesta Key Main Beach

Key Amenities

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

About this property

Water views everywhere from this Penthouse condo on Siesta Key! Taxes (13%) already included in my rates. Walk to beach. King bed in bedroom (and a Queen bed in living room if needed). Come and enjoy beautiful weather at the best beach in Florida! Heated Pools, Lighted Har-Tru Tennis Courts, Fitness...

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Featured review

"Penthouse Paradise"

what a great find! A bright and lovely penthouse condo in a resort on Siesta Key. Easy walk to the beach, and the new Pickleball courts at the Main beach. Harbor Towers itself had a great pool, marina,...

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$195
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 2, 1 bedroom, 1 bathroom
20 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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$212
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
83 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

"Would highly recommend"

First time visiting Siesta Key and staying in this Condo. Everything was already furnished and was just how described and exact pictures as when I booked. Awesome view of the ocean. Saw dolphins a couple...

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$279
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 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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$173
avg per night
Last Minute Deal
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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$279
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
49 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

"Great Location - Amazing"

Views of ocean from Condo were like being on a cruise ship. Area is very quiet and private. Condo has everything you need for your stay. Bed is very comfy, just sits up a little high. Many, many restaurants...

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$255
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...

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$464
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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$265
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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$282
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 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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$308
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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$274
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
17 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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$428
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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$240
avg per night
Siesta Key House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.9 miles to Siesta key

Key Amenities

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

About this property

Comfortable private 3bedroom 2 bath home, open concept floor plan. The master suite is large and open with a sitting area and views of the tropical garden in the back of the house, a full walk in closet and step down shower bath with dual vanities. The next bedroom consist of 2 twin beds with additional...

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Featured review

"Definitely more than 5 stars for this property"

I’ve rented several Siesta Key properties, but this is definitely my favorite. The home is located very close to the public beach down a quiet cul de sac. The neighbors were all friendly and the area...

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$267
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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$274
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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$256
avg per night
Siesta Key Apartment
Sleeps 2, 1 bedroom, 1 bathroom
8 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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$95
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 cozy beach house awaits your visit! Magnificent view of the Gulf of Mexico and evening sunset from lanai.... Peaceful Intercoastal inlet views and sunrise from front door...This little nest has been newly "stem to stern" furnished and equipped for your comfort. Coastal Living as its...

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Featured review

"Perfect sunsets, great lanai and best location"

Nice quiet location on Turtle Beach. Best sunset views, right on the beach and all the amenities one needs for a perfect beach holiday. Added bonus of docks for boats/kayaks, heated pool and gated entry....

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$240
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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$115
avg per night
Siesta Key Bungalow
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

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

Key Amenities

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

About this property

*Calendar month rentals only*May-November (7-month lease) - $3000 per month plus utilities December - $6900 per month plus utilities January, February, March, & April - $9800 per month plus utilities50% deposit upon booking, balance 90 prior for monthly rentals. Check the calendar for...

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Featured review

"We Keep Coming Back"

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

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$100
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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$241
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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$265
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 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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$228
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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$317
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 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

"Great place!"

Everything was as expected, great place to stay! Can’t think of anything else I would have asked for!

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$313
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
52 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

"Beach Bliss"

We thoroughly enjoyed our week vacation in A208 at fisherman cove. The condo was in excellent condition and when we needed help the owner was available give us answers. My wife and I couldn’t have been...

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$418
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

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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$233
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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$240
avg per night
Siesta Key Apartment
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Indulge in a luxurious stay at this completely renovated home in the center of the island, offering a private pool and a tranquil atmosphere. , you can immerse yourself in the beauty of this home. This home is ideal for families with children and infants, providing a perfect blend of comfort and convenience....

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$262
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to paradise at this beautifully remodeled 2-bedroom, 2-bath condo in a tranquil bayside complex on Siesta Key! This third-floor unit boasts a stylish open kitchen with granite countertops and stainless steel appliances, perfect for preparing meals. Enjoy comfortable living with tile flooring in...

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$120
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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$336
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 196 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 $57 per night with an average price per night of $240.

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 93 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!