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Siesta Key Vacation Rentals

(191 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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$268
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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$343
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 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

"Brand new beachfront condo"

Steps from the beach. Quiet location on Turtle Beach with easy access to the free trolley to Siesta Key. Upscale finishes and furniture make this place very desirable.

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$297
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 House
Sleeps 12, 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•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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$696
avg per night

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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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$288
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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$318
avg per night
Siesta Key Cottage
Sleeps 2, 1 bedroom, 1 bathroom
4 reviews

Distance to beach: 0.5 miles to Siesta Key Beach

Key Amenities

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

About this property

*Calendar month rentals only* 2026 May - November (seven-month lease) - $2000 per month plus utilities December - $3900 per month plus utilities January - $5900 per month plus utilities February & March - $6900 per month plus utilities April - $4900 per month plus utilities50% deposit upon...

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Featured review

"Excellent pet-friendly bungalow"

This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where...

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$214
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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$402
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

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

"Spring break"

We very much enjoyed our time at fisherman's Cove. We loved the closeness to the beach and the quieter location! The condo was well stocked and appreciated the beach chairs and towels. We look forward to...

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$294
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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$268
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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$292
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
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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$268
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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$289
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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$370
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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$314
avg per night
Last Minute Deal
Siesta Key House
Sleeps 8, 4 bedrooms, 2.5 bathrooms
10 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

"Fabulous vacation house"

My family, six adults and two young children, had an amazing week at this house on Siesta Key. We loved being able to walk out the door and be on the sand. We made sand castles and swam everyday. It doesn’t...

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$782
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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$163
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
79 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

"Sunsets from our lanai"

This place is great! It sits essentially just a few feet from the beach. The sunset views are stunning. The condo is fully equipped, which anything you need to use on the beach. The pool is great too.

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$291
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
16 reviews

Key Amenities

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

About this property

Complete remodel 2026! 7 DAY Minimum Stay. 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...

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Featured review

"Amazing Beach Condo"

This rental condo is amazing it’s been completely remodeled everything inside is new. It’s on the first so you walk out your door right onto the beach!! Best vacation spot we have ever been to by far!...

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$262
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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$292
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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$288
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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$204
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 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 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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$115
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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$290
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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$252
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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$290
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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$304
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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$107
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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$268
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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$143
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
4 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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$460
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
11 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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$446
avg per night
New
Siesta Key House
Sleeps 2, 1 bedroom, 1 bathroom

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.Immerse...

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$173
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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$234
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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$187
avg per night
Last Minute Deal
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
46 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

"A little piece of Paradise"

My husband and I were in much need of a peaceful relaxing vacation. This is exactly what we got at Kevin and Elaine’s condo on Siesta Key. A very clean and comfortable condo that gave us everything we...

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$418
avg per night
New
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

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

Key Amenities

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

About this property

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

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$291
avg per night
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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$267
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
15 reviews

Distance to beach: 1 miles to Crescent Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

AFTER 2 HURRICANES E91 IS READY FOR GUESTS!! We thank God that our condo was spared! E91 is a completely renovated, First floor Condo, steps to the pool. Master bedroom has a King bed with on-suite bathroom and walk-in closet. Second bedroom has a Queen bed and twin bunk beds. Fully equipped kitchen...

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Featured review

"Best Condo EVER !!"

The HOST of this unit (E91) was the most prepared HOST of all time. She had every box checked inside the condo to make our stay effortless. The grand-children loved the bunk beds in the second bedroom...

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$227
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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$258
avg per night
New
Siesta Key Apartment
Sleeps 2, 1 bedroom, 1 bathroom
10 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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$242
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

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

About this property

This 5th floor two bedroom, two bath condo is totally and completely renovated. Be one of the first guests to stay in this beautifully renovated condo. New tile throughout. There are two bedroom suites with private baths. Each bedroom has new slider doors that open to screened in lanai with beautiful...

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Featured review

"Relaxing getaway"

We had a really nice week in this condo just steps to the beach. The powdery white sand never gets hot.The condo has all of the essentials and more. Very comfortable. And there’s a nice pool if want to...

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$301
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

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

About this property

RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large...

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Featured review

"Beautiful Condo!"

This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen...

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$284
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
7 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

"perfect spot"

Fisherman's cove is the ultimate spot for a peaceful getaway. Your host Carrie is a wonderful, warm and thoughtful person. You won't find anyone better. Her condo Is perfectly located on the corner of the...

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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

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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$290
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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$227
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 191 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 $70 per night with an average price per night of $267.

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