Cheap Vacation Rentals in Siesta Key

(27 rentals)
booking message booking message
Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
10 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

$109

avg/night

$109
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo, ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Absolutely gorgeous property"

Absolutely gorgeous property. The grounds and the property were kept beautifully. All of the amenities that were promised, were there. Being so close to the beach was a plus. There was no need to rent a ...

See all reviews

Show less

Siesta Key Cottage
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
4 reviews

Distance to beach: 0.5 miles to Siesta Key Beach

$139

avg/night

$139
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*May - November (seven-month lease) - $2000 per month plus utilities May - October (three-month lease) - $2900 per month plus utilities December - $4900 per month plus utilities January, February, and March - $5900 per month plus utilities April - $4900 per month plus ...

View all property information

Property Type

Siesta Key Cottage

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 ...

See all reviews

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$144

avg/night

$144
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

You will love the grounds with 7 acres of lush tropical landscaping. Our unit is complete with coastal décor, newer appliances and washer/dryer. Walk to Siesta Key Beach or swim in the heated pool. We have several grills, a clubhouse with library, and a peaceful lagoon. Siesta Key Village is filled ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
2 reviews

$147

avg/night

$147
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Renovated 1/1 condo with everything you need to relax or work from home! Bedroom offers a king size bed, large closet, dresser, two nightstands with storage, desk equipped with keyboard, mouse, printer and laptop stand, and large TV with WiFi connection to watch all your favorite apps. There’s also ...

View all property information

Property Type

Siesta Key Condo

Featured review

"We enjoyed your wonderful condo!"

We really enjoyed your beautiful condo and we’re so comfortable there and had a great time. We loved the beach-themed decorating so much And the king sized bed was so cold for table that we want to buy ...

See all reviews

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 1 miles to Crescent Beach

$150

avg/night

$150
avg per night
View Details

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 ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Great Condo"

My husband and I were very happy with this condo, it has great colors and craftsmanship in the upgrades. The condo is clean, comfortable and spacious: it also has all the necessary amenities for living ...

See all reviews

Show less

Siesta Key Studio
Studio | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 0 bedrooms, 1 bathroom
3 reviews

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

We are proud of our Siesta Key Condo at Ebb Tide. This Florida Beach Rental is in the heart of Crescent Beach. Once you park your car there is no need to use a car for the rest of your stay. A short 1 1/2 block walk and your toes are enjoying the lush, white (quartz) sands of the crescent beach.The ...

View all property information

Property Type

Siesta Key Studio

Featured review

"A little piece of Paradise."

The condo was absolutely amazing, and very affordable. Perfect for a couple, so close to the bay and the beach. The condo had everything needed for our stay. Will definitely book again. I love going to ...

See all reviews

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

$155

avg/night

$155
avg per night
View Details

Key Amenities

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

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Very nice host and home. Home needs work."

The owner could not have been nicer. The home is beautiful but does need attention to details like, no ice from icemaker, hot water takes forever to get to kitchen and master bath. Carpet in bedroom needed ...

See all reviews

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$158

avg/night

$158
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Beautiful ground floor unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Unit sleeps 4, 2 Cable TV's , wireless internet ( Siesta 4 Rent is not responsible for tech support), community coin laundry right outside the door, covered parking, community pool ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
7 reviews

$159

avg/night

$159
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our little piece of paradise is a one bedroom condominium ideal for couples or young families. We are located at 73 Avenida Messina in unit #7 on the ground floor of the Gulf Holiday Apartments. We are 300 ft. from the Gulf of Mexico and about a five minute walk from the village - known for its shops, ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Condo #6"

We enjoyed staying in Condo #6 for two nights before Hurricane Helene arrived. We evacuated and weren’t able to return. We hope to stay here again in the future. We have stayed in these condos for ...

See all reviews

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$161

avg/night

$161
avg per night
View Details

Key Amenities

  • Pet friendly
  • WiFi

About this property

Quaint 1 bedroom bungalow with Murphy Bed that folds into the wall during the day providing additional living space. Living room w/leather furniture, french doors opening to a private brick patio. 2 Smart TV's. 43 inch in living room and 32 inch in bedroom. Kitchen offers a mini convection oven ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

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

$162

avg/night

$162
avg per night
View Details

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 ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Siesta Sand Dollar"

We had an amazing stay at Maria's place at Siesta Harbor. Everything had just been updated and was very modern and beautiful. We would highly recommend her unit and we are looking forward to going back ...

See all reviews

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.0 miles to Siesta Key Main Beach

$163

avg/night

$163
avg per night
View Details

Key Amenities

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

About this property

Water views everywhere from this Penthouse condo on Siesta Key! Come and enjoy beautiful weather at the best beach in Florida! Heated Pools, Lighted Tennis Courts, Fitness Gym, locker rooms, Marina, kayak launch, covered bike storage, and easy walk to SiestaKey Main Beach, and its new pickleball courts! ...

View all property information

Property Type

Siesta Key Condo

Featured review

"hurricane"

Unfortunatley we cancelled are vacation because of the back to back hurricanes Siesta Key suffered. We were very disappointed. The owner, Sue, was such a pleasure to work with. We would love to be able ...

See all reviews

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 800 feet to Siesta Key Beach

$165

avg/night

$165
avg per night
View Details

Key Amenities

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

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
10 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

$169

avg/night

$169
avg per night
View Details

Key Amenities

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

About this property

Sweet Siesta Key Condo, Spacious and Quiet One Bedroom with King Bed. Walk right over to Siesta Key Main Beach. Please note that RATES ALREADY INCLUDE 13% TAXES. Condo is walking distance to Siesta Key Main Beach, entrance crops the street from this complex. And you are also a nice 0.8 mile sidewalk ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Great place to stay"

Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my ...

See all reviews

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
26 reviews

Distance to beach: 0.1 miles to Siesta Key Beach

$170

avg/night

$170
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

NEWLY UPGRADED - BEAUTIFUL CONDO FOR THE PERFECT GETAWAY FROM THE COLD Right across from Siesta Key Beach, minutes from Siesta Key Village - or the South Village - shopping, top restaurants, live music, and entertainment. Walk , bike or take the free trolley.Sit on the balcony for a quiet and ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Spectacular Vacation"

My husband and I booked this perfect condo in a wonderful location. The condo was spacious, comfortable and beautifully decorated. The beautiful sandy beach was right across the road. We enjoyed hanging ...

See all reviews

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.3 miles to Siesta Key Beach

$172

avg/night

$172
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Renovated 2BR (one queen size & 2 single beds) 2 Bathrooms 2nd floor condo and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings & paved stones drive and covered parking, newly installed luxury wood-like flooring a comfortable ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Beautiful condo"

We spent a month at this beautiful condo. It was very well equipped with everything we needed. Lovely warm pool and such a short walk to Siesta Key Beach. Thank you Lynette (the owner) for making this ...

See all reviews

Show less

Siesta Key Condo
2 BR | 1.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1.5 bathrooms

Distance to beach: 250 feet to Siesta Key

$172

avg/night

$172
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

$176

avg/night

$176
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living. ...

View all property information

Property Type

Siesta Key Condo

Featured review

"March Getaway!"

Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.

See all reviews

Show less

Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$179

avg/night

$179
avg per night
View Details

Key Amenities

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

About this property

Beautiful house on Siesta Key with private pool and generous space. 15 min walk to the beach! This charming 3-bedroom, 2-bathroom private home is located in discreet residential neighborhood, on the beautiful Siesta Key island. It offers a large fenced outdoor area, with a private pool, plenty of parking ...

View all property information

Property Type

Siesta Key House

Featured review

"great location to the Village and beach"

A wonderful location on Siesta Key--we loved being able to walk to the Village and easily walk to the beach. The house has an open feeling with a large living/eating/kitchen area. I cooked a good bit ...

See all reviews

Show less

Siesta Key Condo
Studio | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 0 bedrooms, 1 bathroom

$180

avg/night

$180
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

GROUND FLOOR STUDIO LOCATED IN THE MIDDLE OF THE CASA MAR COMPLEX. SHORT DISTANCE FROM THE BEACH AND POOLS. UNIT OFFERS A BRAND NEW QUEEN MURPHY BED, 32" LCD FLAT SCREEN TV, DVD / VCR AND CD PLAYER. 1 COVERED PARKING SPACE. COMPLEX OFFERS 2 POOLS, TENNIS, SHUFFLE BOARD AND BEACH CHAIRS. COMPLEX ALSO ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
10 reviews
owner special
Owner special: With Easter late this year, our 2 BD is open from 4/19 - 4/26/25. Mention this ad and get 10% off.

Distance to beach: 0.3 miles to Crescent Beach on Siesta Key

$182

avg/night

$182
avg per night
Owner special:
With Easter late this year, our 2 BD is open from 4/19 - 4/26/25. Mention this ad and get 10% off.

View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal ...

View all property information

Property Type

Siesta Key Condo

Featured review

"Siesta key condo"

Absolutely loved our stay at Siesta Key. The condo is clean, well equipped with everything you need, easy access to food and the beach. Would definitely stay here again

See all reviews

Show less

Siesta Key Apartment
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
6 reviews

$182

avg/night

$182
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Vacation rental close to the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.*** It seems like a miracle that Midnight Cove II again was extremely ...

View all property information

Property Type

Siesta Key Apartment

Featured review

"Perfect"

We spent 18 days at the unit. The Unit is beautiful and clean. We enjoyed the location and hope to return next year.

See all reviews

Show less

Siesta Key Bungalow
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
6 reviews

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

$184

avg/night

$184
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*May-October (3-7 month lease) - $3900 per month plus utilities and tax. November & December - $6900 per month plus utilities January, February, & March - $9800 per month plus utilities April - $7900 per month plus utilities 50% deposit upon booking, balance ...

View all property information

Property Type

Siesta Key Bungalow

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 ...

See all reviews

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$191

avg/night

$191
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful 1 Bedroom w/ den in Bayside community of Bay Oaks. 3 TV's, 1st floor unit. Sleeps 4, King in the master bedoom. The den has a twin bed and the livingroom has a sleeper sofa. No cable, Streaming only. Highspeed internet. (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT).1 week min. CLEANING ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$191

avg/night

$191
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 4TH FLOOR AND IS A 1 BEDROOM / 1 BATH CORNER UNIT. WASHER/DRYER IN UNIT. COMPLEX OFFERS POOL, TENNIS, 1 ASSIGNED COVERED PARKING SPACE. UNIT HAS 2 TV'S, DVD. HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Bungalow
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

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

$193

avg/night

$193
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*May-October (six-month lease) - $3900 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $9800 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

View all property information

Property Type

Siesta Key Bungalow

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 ...

See all reviews

Show less

Siesta Key Studio
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
5 reviews

Distance to beach: 0.3 miles to Siesta Key Beach access 10

$200

avg/night

$200
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*******SPECIAL - February, March, and April 2024 - $200 per night plus utilities - 14 night minimum****May - November (seven-month lease) - $1750 per month plus utilities May - November (three-month lease) - $2500 per month plus utilities December - $3900 per month ...

View all property information

Property Type

Siesta Key Studio

Featured review

"Perfect peaceful pet friendly bungalow"

I recently had the pleasure of staying for three months in this cozy bungalow on Palm Island in the heart of Siesta Key. Nestled amidst lush vegetation and just a short walk from the beach and Siesta Key ...

See all reviews

Show less

Map
Expand map Close map
Siesta Key Vacation Rentals