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Siesta Key Vacation Rentals

(188 rentals)
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
78 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

"PERFECT BEACH CONDO"

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

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$300
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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$352
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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$296
avg per night
Siesta Key Townhome
Sleeps 6, 3 bedrooms, 3 bathrooms
14 reviews

Distance to beach: 0.3 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Featured review

"Great location!!!"

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

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$471
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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$308
avg per night

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Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 100 yards to Turtle Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Enjoy your home away from home in beautiful Siesta Key! This great 2-bedroom, 2-bath has everything you need for a wonderful, relaxing vacation. This prime location makes it convenient to get to the beach. Just walk a single flight of stairs (or elevator) and you're on the beach where you can enjoy...

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$300
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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$297
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
43 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 ocean front condo"

Condo was clean and well stocked. Loved being able to easily get to beach. My husband enjoyed fishing. Listened to the ocean from the screened in porch. Beautiful views.

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$263
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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$323
avg per night
Siesta Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

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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$405
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

Great house as is renovate december-2024 with new kitchen, toilets, furniture and everything is painted inside the house on Siesta key with pool and kanal. You can do fishing on the backside or have a jetski, boat there. Sometime you can see manates on the kanal. 3 bedroom with 3 bath and a nice heated...

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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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$371
avg per night
Siesta Key Apartment
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

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 new tile flooring, a gourmet kitchen...

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Featured review

"The best"

Before coming here The condo pictures showed remodeling close proximity to the ocean And the pictures were true It was equipped with everything we needed it was on the quiet side of the key We will be back

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$296
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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$300
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
11 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"

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

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

Key Amenities

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

About this property

MONTHLY RENTAL. Introducing our BEAUTIFUL NEWLY RENOVATED LISTING! Nestled within this premier condominium complex, our home offers direct access to the highly acclaimed Siesta Key Beach without the need to cross any streets.Our home away from home is perfect for those seeking a winter retreat or...

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Featured review

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

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

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$314
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

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

"An Unforgettable Beachfront Retreat"

We recently had the pleasure of staying in a beautiful beachfront condo at Fisherman's Cove, and everything about our experience was absolutely fabulous.From the very beginning, Frank was incredible...

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$307
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
44 reviews

Key Amenities

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

About this property

Stunning Oceanfront Condo on Siesta KeyStep into your private paradise! This condo offers breathtaking ocean views from the living room, master bedroom, kitchen, and lanai. Imagine waking up to the sound of waves and ending your day with the sun dipping into the Gulf—this is coastal living at...

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Featured review

"Fabulous Retreat on the water"

Our week at Kevin and Elaine’s place delivered everything we wanted. Waterfront access with the best sunsets around. We even had a pod of dolphins come by for a visit! The condo was super clean and well...

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$480
avg per night
Siesta Key House
Sleeps 16, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

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

About this property

Key Differentiators & Amenities•360 steps to 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, bowls, blankets, waste bags •4...

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$783
avg per night
Siesta Key Villa
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

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

"Highly Recommend!"

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

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$314
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
9 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

"Beyond Expectations"

Just finished our stay in Condo A306 and the entire experience was spectacular! The view of the Gulf and its amazing sunsets were the VERY BEST we have ever seen!! You are literally 20 yards from the ocean...

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$319
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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$181
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

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

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Featured review

"Great location!"

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

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$191
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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$531
avg per night
New
Siesta Key Apartment
Sleeps 2, 1 bedroom, 1 bathroom
3 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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$240
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Gorgeous unit and beautifully furnished with an incredible 2nd floor view of the Gulf of America. Sleeps six comfortably with a king master and a full-size bed along with a twin in the guest room, plus a queen sleeper sofa. beach chairs and toys for your enjoyment. You will not want to leave once you...

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Featured review

"Amazingly Fantastic."

The beach, Turtle Beach, not so great, but good to soak up the sun and be close by. Amenities were very good, staff exceptional, condo was awesome. Everything needed was there. Very clean, neat,

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$286
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
5 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

"1st Sojourn to Siesta Key"

Very much enjoyed our travel South to escape Northern Winter Vortex. Siesta Harbor newly decorated Unit was nicely located, walking distance to nearby restaurants, shops and market. Especially enjoyed safe...

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$156
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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$306
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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$323
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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$300
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 0.7 miles to Turtle Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Welcome to Bayside Haven at the Pointe, your perfect getaway nestled along the serene shores of Sarasota Bay. This charming vacation rental features two spacious bedrooms and two full bathrooms, ensuring ample comfort and privacy for you and your guests.The fully equipped kitchen is perfect for preparing...

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$144
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% Credit...

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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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$418
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 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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$452
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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$229
avg per night
Last Minute Deal
Siesta Key House
Sleeps 7, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 0.7 miles to Siesta Key Beach

Key Amenities

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

About this property

**Completely Renovated February 2025** Welcome to island life! Enjoy your own private resort in the heart of the #1 beach in America, Siesta Key!Indulge in the pinnacle of island living at this pristine waterfront home on Siesta Key—a haven where luxury meets natural beauty. In the heart of...

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Featured review

"Beautiful and comfy"

5 stars. Wish I could give 10. Beautiful and comfy cozy home, comfortable beds, gorgeous pool, so kid friendly and lovely views from the fire pit. The decor is top notch!! Danielle and Jeb were great-...

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$726
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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$299
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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$323
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
49 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

"Everything you could wish for!"

From the moment we walked in, we were impressed! The condo is beautifully decorated and thoughtfully equipped with everything you need. The view from the room is breathtaking. One step out of the lanai...

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$298
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

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

About this property

Crystal Sands, Siesta Key, SarasotaAmazing Views!! Our property is right on the beach. Take the elevator down and you're at the ocean. The views are amazing as you can see in the pics. Sit on the lanai for breakfast and watch the activities on the beach, or have a glass of wine and watch...

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Featured review

"AMAZING 2-Weeks!!!!!"

We loved every minute of our 2-week stay at Crystal Sands, the unit was beautiful and views breathtaking. We were a stones throw from the beach and it couldn't have been any better. I highly recommend!

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$443
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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$170
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 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

"Wonderfully Relaxing"

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

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$315
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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$314
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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$229
avg per night
Special Offer
Siesta Key Condo
Sleeps 4, 2 bedrooms, 1.5 bathrooms
37 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

"Happy place ."

The condo had all the little things that we so appreciate , fabulous linens and the towels were top notch. Also the shower had fantastic pressure some times rare in a rental. The landscaping and canal views...

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$216
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 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 beach view"

Place is awesome and Kathy is best host.Right on beach and restaurants within walking distance. Had a couple of questions and Kathy got back to us right away. If you like the beach, you will love this place.

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$386
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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$227
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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$314
avg per night
Siesta Key Villa
Sleeps 5, 2 bedrooms, 2 bathrooms
17 reviews

Distance to beach: 400 yards to Crescent Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

The Sand Dollar is a private villa located at the quiet, well run and exceedingly clean "beach to bay" community of Horizons West. A maximum of 50% of Horizons West properties are rented so the community has a more residential feel than many others on the island. The villa has been recently...

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Featured review

"Beautiful villa"

Villa E8 was attractively decorated and well equipped. Property was clean and well maintained. Property management company was very responsive. Weekly linen service was a nice surprise.

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$295
avg per night
Siesta Key Bungalow
Sleeps 4, 2 bedrooms, 2 bathrooms
6 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 and tax. November & December - $6900 per month plus utilities January, February, March, & April - $9800 per month plus utilities50% deposit upon booking, balance 90 days prior for monthly rentals. Check...

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Featured review

"A Great Home Away from Home"

I loved my two months at Blue Lagoon. It has a great location, near the beach and the village. Palm Island is a great neighborhood, a secluded enclave within Siesta Key. I got to know a lot of my neighbors...

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$148
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 $87 per night with an average price per night of $288.

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