Siesta Key Vacation Rentals, Condos, & More

51-73 of 73 Siesta Key Rentals

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Siesta Key Florida Vacation Rentals - Home
1 / 28

Siesta Key Home
4 Bedrooms / 2 Bathrooms / Sleeps 11

“ Excellent ”7 Reviews

from

$425

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:11
Type:Home
Per night:$425 - $495
Per week:$2,975 - $3,465
Pets allowed:No
Internet:Yes

Directly overlooking breathtaking views of privately owned beach on North end of Siesta Key. Just renovated everything brand new. Four bedrooms, 2 baths, sleeps 11, living room, dining room, full kitchen and game room. Flat screen TVs in living room, game room, and each bedroom...

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Wonderful location, units, & family!

“ Excellent ”
January 16, 2015
It doesn't get any better! We rented the property for a week of wedding adventures and it was lovely! Low key enough, beautifully maintained, clean, fresh and beach front! Easy to hang out on the property and cook your own meals, enjoy the hammock, or a short walk to all the restaurants and shopping your heart could desire The evenings around the fire-pit and the days at the beach were incredible. . People who own/rent the property were a delight! We will return!
Kay Miller, Memphis, TN

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Siesta Key Florida Vacation Rentals - Condo
1 / 7

Siesta Key Condo
2 Bedrooms / 3 Bathrooms / Sleeps 6

from

$295

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Condo
Per night:$295 - $445
Per month:$8,850 - $13,350
Pets allowed:Yes
Internet:Yes

Privacy, Luxury, 99 steps to the Beach. The Master Bedroom has a King size Bed and Glamorous Bath. Second Bedroom has a Queen Bed and Private Bath. The Den has a Pullout Sleeper Sofa plus a (newly installed) First Quality Murphy Bed. Fully equipped GOURMET style kitchen with...

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Siesta Key Florida Vacation Rentals - Home
1 / 11

Siesta Key Home
4 Bedrooms / 2 Bathrooms / Sleeps 9

“ Excellent ”2 Reviews

from

$158

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:9
Type:Home
Per night:$158 - $258
Per week:$1,100 - $1,800
Pets allowed:Yes
Internet:Yes

Your home away from home- - our beautiful four bedroom house is located in a quiet, upscale neighborhood only two blocks to Siesta Beach, the largest and most beautiful beach on the key. We are also an easy walk to the Village for restaurants, shopping and entertainment. Our...

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Dream place!

“ Excellent ”
August 28, 2014
Perfect place to spend vacations with the family. Perfectly clean, with a great kitchen equipment, very good matresses, and a lot of outdoor activities equipment. Great clean pool in a garden with privacy. Calm, sunny and close (10mn walking distance) to beautiful Siesta key!
Anne Closuit, New-York, USA

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Siesta Key Florida Vacation Rentals - Condo
1 / 14

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$160

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$160 - $250
Per week:$1,120 - $1,745
Pets allowed:No
Internet:Yes

Welcome to a bit of heaven! Newly udpdated throughout including large flat panel HDTV with PREMIUM CABLE including HBO, DVR and WIRELESS INTERNET FREE! A gorgeous gulf- front vacation awaits you as you come and enjoy this enchanting condo! Located directly on newly replenished...

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Siesta Key Florida Vacation Rentals - Condo
1 / 6

Siesta Key Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

from

$295

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$295 - $445
Per month:$8,850 - $13,350
Pets allowed:Yes
Internet:Yes

The Master Bedroom has a King size bed and Glamorous Bath. Second Bedroom has a Queen size bed and a second private bath. The Den has a Queen size Sleeper Sofa. Fully equipped Cottage Style Kitchen with Corian countertops. Washer and Dryer, WIFI, Tropical patio / Pool, plus lounge...

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From the beach
1 / 8

Siesta Key Home
3 Bedrooms / 3.5 Bathrooms / Sleeps 7

“ Excellent ”1 Review

from

$229

/ night

Email Owner
Bedrooms:3
Bathrooms:3.5
Sleeps:7
Type:Home
Per night:$229 - $286
Per week:$1,600 - $2,000
Pets allowed:Yes
Internet:Yes

Tiffany Sands is a group of 9 townhouses directly on Crescent Beach. Our beach house is a stand alone unit(unattached). We have full gulf views with 2 decks facing the Gulf of Mexico. It is a spacious 1, 800 sq. ft. and newly decorated with a fully appointed kitchen, plus 3 1/2 ...

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Absolutely Amazing

“ Excellent ”
November 20, 2014
When we pulled into Tiffany Sands, we knew it was going to be something special! We had a week of pure bliss. The amenities were unbelievable. Every morning we were greeted by warm sun and the sound of rolling waves. One of the many benefits of this rental was that you had your own beach that was off of the beaten path. The main beach is withinn walking distance but you would never know that you were even close. We leisurely walked outside and down the path to what we called "our spot" on the beach. We even made friends as we were the only ones in our small section of beach everyday. The property leaves no stone unturned in how nice it is. The master bedroom is amazing and the view from the balcony makes it even better! We travelled with 3 couples and had an amazing time. If I would have had a family and kids, this would be a prime location for all family vacations. Do not overlook this property as you will be absolutely amazed!
Scott Schenker, Orlando, FL

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Siesta Key Florida Vacation Rentals - Condo
1 / 24

Siesta Key Condo
2 Bedrooms / 1.5 Bathrooms / Sleeps 4

“ Excellent ”4 Reviews

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:4
Type:Condo
Per night:$97 - $204
Per week:$675 - $1,428
Pets allowed:No
Internet:No

Sun, Sand & SAVE 20% to 50% per Week at Midnight Cove #714, Direct- with- Owner "All- In Price" DISCOUNTED RENTAL RATES from $655 to $1, 262 /Wk & SAVINGS from $239 to $640 /Wk depending on the Number of Weeks Rented, and on the Season. Contact owner if you wish to make an...

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Convienent location

“ Excellent ”
July 11, 2014
This rental was awesome! Location, location, location! The nice shaded area off of the back porch was a welcoming place for morning coffee. Easy rental through owner. Midnight Cove providing beach chairs and umbrellas is a big PLUS! easy access to the beach. Condo had everything you need. Nice and clean gas grills near condo were perfect! We would definitely stay here again!
Jennifer Legendre, Louisiana

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Siesta Key Florida Vacation Rentals - Condo
1 / 8

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”1 Review

from

$200

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$200 - $217
Per week:$1,400 - $1,517
Pets allowed:No
Internet:No

Casarina is the most prestigious building on Siesta Key. With only 88 units Casarina is upscale, quiet and friendly. It sits on a private beach on the world famous Crescent Beach (rated one of the top 10 beaches by The Travel Channel). Our spacious 1, 500 sq. ft. condo, is on...

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Couldn't be more perfect!

“ Excellent ”
August 22, 2014
We've just returned from taking our son down to college in Sarasota and we stayed at this most perfect 2 bdrm condo right on the fabulous Crescent Beach with a beautiful swimming pool and wonderful views of the gulf. We plan to book this condo whenever we go to Sarasota!
Sherry Mandel, Hudson Valley, NY, USA

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Siesta Key Florida Vacation Rentals - Home
1 / 24

Siesta Key Home
7 Bedrooms / 5 Bathrooms / Sleeps 16

from

$999

/ night

Email Owner
Bedrooms:7
Bathrooms:5
Sleeps:16
Type:Home
Per night:$999 - $1,500
Per month:$29,970 - $45,000
Pets allowed:No
Internet:Yes

This stunning home features 10 foot ceilings, top of the line VIKING appliances including a wall mounted double oven, stove, and side by side refrigerator. The kitchen has a massive center island with lots of room for multiple chefs or families and friends to sit and chat after...

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Siesta Key Florida Vacation Rentals - Villa
1 / 8

Siesta Key Villa
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$258

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Villa
Per night:$258 - $486
Per week:$1,800 - $3,400
Pets allowed:No
Internet:Yes

Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and gaze across the expansive living area, then further...

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Siesta Key Florida Vacation Rentals - Condo
1 / 9

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$123

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$123 - $210
Per week:$860 - $1,464
Pets allowed:No
Internet:Yes

A warm welcome to our Gulf view condominium at wonderful Siesta Key! We have the best location - - across from the Siesta Public Beach, and walking distance to Siesta Village that offers great gourmet dining, shopping, and entertainment. The condo has beach décor with cheerful...

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Best Vacation Ever

“ Excellent ”
April 25, 2014
Great place, all the amenaties you could ask for. Amazing view of the beach! close to town.
Sandy Creagan, Tempe, Arizona USA

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Siesta Key Florida Vacation Rentals - Apartment
1 / 4

Siesta Key Apartment
1 Bedroom / 1 Bathroom / Sleeps 4

from

$295

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$295 - $360
Per month:$8,850 - $10,800
Pets allowed:Yes
Internet:Yes

This 1 bedroom Beach Suite is totally newly remodeled with a tiled Kitchen and Bath with new furnishings throughout. This property is right on the sandy beach, The Sandbox has the best of it all. It is like small town USA combined with one of the top beaches in the world. The...

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Siesta Key Florida Vacation Rentals - Condo
1 / 24

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”32 Reviews

from

$139

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$139 - $255
Per week:$973 - $1,781
Pets allowed:No
Internet:No

Sun, Sand & SAVE 20% to 50% per Week at Siesta Breakers #603, Direct- with- Owner "All- In Price" DISCOUNTED RENTAL RATES from $944 to $1, 728 /Wk & SAVINGS from $374 to $973 /Wk depending on the Number of Weeks Rented, and on the Season. Contact owner if you wish to make ...

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Beautiful Beach

“ Excellent ”
July 14, 2014
This was our first trip to Siesta Key, but not our last! We are already booking another stay at Siesta Breakers for next year. It is a great location on the Beach and great access to the mainland.
Helen Hussey, Vidalia, GA

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Siesta Key Florida Vacation Rentals - Condo
1 / 11

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”4 Reviews

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$107 - $114
Per week:$747 - $794
Pets allowed:No
Internet:Yes

Location, Location, Location! Siesta Key #1 Beach in USA Our condo is only a 3 minute walk to Crescent Beach on beautiful Siesta Key FL. Siesta Key Beach rated #1 beach in the USA. We rent by the month or for the season. Our two bedroom, two bath has a screened in lanai, large...

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Really Nice Condo!!

“ Excellent ”
August 30, 2013
We recently stayed at this condo for a few weeks. The condo is in very good shape and is charming. The management staff is amazing and always easy to reach. Very close to the beach and the pool. Overall, we had a pleasant experience.
tanya yudin, Washington

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Siesta Key Florida Vacation Rentals - Condo
1 / 22

Siesta Key Condo
1 Bedroom / 1 Bathroom / Sleeps 4

from

$125

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$125 - $255
Per month:$3,750 - $7,650
Pets allowed:Yes
Internet:Yes

Village West # 101 is the perfect place for your Siesta Key Vacation. With rentals by the day, by the week, or longer this location is sure to please. Our newly Remodeled Siesta Key Ground Floor Apartment is in the heart of the Village of Siesta Key. This apartment is well appointed...

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Siesta Key Florida Vacation Rentals - Home
1 / 21

Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 7

“ Excellent ”5 Reviews

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:7
Type:Home
Per night:$350 - $500
Per week:$2,400 - $3,400
Pets allowed:Yes
Internet:Yes

BEACH FRONT :Wander out 100 yards to the gorgeous white sand beaches of the Gulf of Mexico and only one block to SIESTA KEY VILLAGE! Our gorgeous three bedroom two bath beach- house is a one- of- a- kind private home with amazing water views from the private patio, (grilling on ...

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Wonderful Vacation

“ Excellent ”
December 11, 2014
Light, airy, attractive condo perfectly situated next to the beach and Siesta Key Village. Our days were filled with the beach, lunch (sometimes back at the condo, sometimes on the beach), beach, a coctail and "apps" in the village and back to the beach to look at the sunset. This was followed by dinner and bed. Wake up and do all over again. A wonderful time and we can't wait to do it again at Barb and Jay's!
Wendy Sinclair, Boston, MA

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Siesta Key Florida Vacation Rentals - Home
1 / 12

Siesta Key Home
4 Bedrooms / 3 Bathrooms / Sleeps 10

from

$258

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:10
Type:Home
Per night:$258 - $515
Per week:$1,800 - $3,600
Pets allowed:No
Internet:Yes

Welcome to “Casa De Suenos”, one of the most fabulous vacation homes in Siesta Key. Newly constructed in 2013! The magic begins as you enter the foyer of this beautiful casa and gaze across the expansive living area, and deck area. You know already you made the right choice...

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Siesta Key Florida Vacation Rentals - Condo
1 / 6

Siesta Key Condo
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”6 Reviews

from

$485

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$485 - $570
Per month:$14,550 - $17,100
Pets allowed:Yes
Internet:Yes

This 3 bedroom 2 Bath Beach Suite is totally newly remodeled with a tiled Kitchen and Bath with new furnishings throughout. This property is right on the sandy beach, The Sandbox has the best of it all. It is like small town USA combined with one of the top beaches in the world....

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Fabulous beachfront property

“ Excellent ”
January 22, 2014
We had a family gathering here (4 days) & it was wonderful in every way! None of us had ever been to Siesta Key & felt so fortunate to find such nice accommodations --& liked the location, as the north end of the island is much less crowded than the middle & southern end--yet only couple of blocks from the Village shops & restaurants. The condo was, as described, newly renovated & well furnished. There is a large patio facing the beach---perfect for eating outside & enjoying the sunsets. They even had a generous supply of beach chairs which we could take to the beach. The condo was also very clean. Nice touches like coffee, sugar, creamer, salt, pepper, kleenex , soap, shampoo, etc. The whole staff was very nice & helpful. Frank, the manager & Roger, the owner, gave us wonderful recommendations for restaurants. It was an added pleasure to have our dogs there with us---very dog friendly place. We plan to come back & stay longer!
Grace Gokturk, Naples, FL & Fairfield Bay, AR

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Siesta Key Florida Vacation Rentals - Apartment
1 / 3

Siesta Key Apartment
Studio / 1 Bathroom / Sleeps 2

from

$185

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$185
Per month:$5,550
Pets allowed:Yes
Internet:Yes

Beachfront charming Studio directly on Gulf of Mexico. Queen size comfortable Murphy bed plus a Futon. Galley kitchen with full size refrigerator. Propane BBQ plus umbrella table, four chairs. Beach chairs. WIFI, Cable TV, Air conditioned, of course. Ground floor. Walk to Siesta...

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Siesta Key Florida Vacation Rentals - Villa
1 / 16

Siesta Key Villa
2 Bedrooms / 1 Bathroom / Sleeps 6

“ Excellent ”6 Reviews

from

$118

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Villa
Per night:$118 - $160
Per week:$820 - $1,120
Pets allowed:No
Internet:No

Dr. Beach voted Siesta Key Beach the #1 Beach in USA 2011. If you are looking for a vacation condo rental in Siesta Key, Florida for your Florida holidays and family beach vacation please consider my villa rental in Siesta Key, FL. It is a tastefully furnished and fully equipped...

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Paradise Perfection

“ Excellent ”
May 2, 2013
Great location, well stocked and clean villa that suited our needs and wants perfectly! Will defiantly stay again! Staff at Casa Blanca are extremely friendly and very helpful. 5 stars for them!
Rachel Roberts, Central Minnesota

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Siesta Key Florida Vacation Rentals - Home
1 / 19

Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$229

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$229 - $358
Per week:$1,600 - $2,500
Pets allowed:No
Internet:Yes

NEW! HEATED POOL! READY FOR OCTOBER 2014! Sophie’s Cottage ( 2 week minimum Rental ) is a smart, sophisticated upscale waterfront retreat with an oversized hot tub, boat dock, and a short walk to Siesta Key Beach. Ideally, it accommodates 6 but can easily sleep up to 8 with...

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Siesta Key Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:No

This is a mediterranean style home with large, with 3 comfortable bedrooms, 2 full baths, beautiful- large kitchen with a family room, formal dining room- living room. The house has natural lights all over the house, and each room has a fan. The floors are natural travertine.,...

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Siesta Key Florida Vacation Rentals - Condo
1 / 21

Siesta Key Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”6 Reviews

Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

2Bed/2Bath Condo Just renovated/modernized with the latest & best kitchen appliances, furniture, pictures and other decorations, and freshly painted through- out with Full Bay Views ! ! ! Bay Tree Amenities include: - 2 Heated Pools (1- Bayside & 1- Oceanside) - Picnic/BBQ...

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Fabulous Month

“ Excellent ”
March 31, 2013
Thank you Jennifer and Andy for allowing us to stay in your lovely condo for the month of March. The condo couldn't have been more perfect. Beautifully decorated and so comfortable. The month could have been a bit warmer but with our lovely home away from home we were very comfortable. The well protected pool let us get all the sun that we wanted. Even on days that were a bit cool the pool was always a welcome sight to many. We hope we get the opportunity to stay in your lovely condo once again. Jennifer thank you for the great correspondence and being so helpful. Warm Regards, Rog & Lela
Lela Thurow, Scottville, MI. USA

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