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From $154 per night (USD)
VRBO
Beach apartment…Sun ,air , water -best friends
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
11:02 1 Beach life in this renovated seaside condo overlooking the Gulf of Mexico from your veranda. there is a heated ...
From $154 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Expansive Renovated Condo, Heated Pools, Tennis, Fishing on Intracoastal | Siesta Key Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Harbor Towers 4th Fl Modern 3BR with Den! This newly remodeled 3-bedroom (plus den with sleeper sofa), 3 ...
From $193 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Walk to Beach, Siesta Key Villa 2, Pool View. Daily Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Villa 2 is overlooking the swimming pool Private entrance with self check in key pad entry All Ground Floor, King size b ...
From $267 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Upscale Vacation House in South Venice
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Upscale modern luxury South Venice house 3 bedrooms, 2 baths, 2000 sf, high ceiling, modern Italian furniture. 10 min sh ...
From $230 per night (USD)
Expedia
From $164 per night (USD)
VRBO
Beach Front Condo, Venice, Florida. 2 bedroom, 2 bath, heated pool.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Totally renovated 2 bed and 2 bath condo on private beach, 1/2 mile to down town Venice and short walk to the Venice j ...
From $164 per night (USD)
VRBO
From $305 per night (USD)
Expedia
Crescent Beach Escape – 2BR Beachfront Condo on Siesta Key Steps to the sand!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
**Welcome to your slice of paradise — a beautifully remodeled 2-bedroom, 2-bath condo right on Crescent Beach in Siesta ...
From $305 per night (USD)
Expedia
From $305 per night (USD)
VRBO
Location, Location! Sarasota Rambler Downtown MidMod Stay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our recently updated 1200 square foot mid-century rambler home is located in the charming downtown Sarasota neighborhood ...
From $305 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Condo# 404 Beautiful Gulf View on Siesta Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This Two Bedroom, One Bath condo is just steps to the white, powdered sugar sand of Siesta Key. Here at La Siesta Condom ...
From $280 per night (USD)
Expedia
From $763 per night (USD)
VRBO
3 BR Siesta Key Mid-Century Oasis w/Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home with a pool. This tropical retrea ...
From $763 per night (USD)
VRBO
From $259 per night (USD)
Expedia
UPDATED & VERY CLEAN 2 BDRM/2 BTHRM just Minutes to Siesta Key!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 2 bedroom, 2 bathroom, ground-floor condo has been completely redone with your comfort in mind. All new furnishings ...
From $259 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Crystal Sands Tower Unit 508 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $486 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Crystal Sands Tower Unit 605 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Treat yourself to a completely remodeled and updated 6th floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...
From $481 per night (USD)
Expedia
From $423 per night (USD)
VRBO
Crystal Sands Villa 15 - Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This 2 bedroom 2 bath villa provides Gracious living with touches of luxury in this completely equipped apartment with p ...
From $423 per night (USD)
VRBO
From $1368 per night (USD)
VRBO
Luxury Waterfront Home w/ Private Heated Pool & Hot Tub | Walk to Lido Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to your private slice of paradise on St. Armands Key. Perfectly positioned on a wide canal with direct access to ...
From $1368 per night (USD)
VRBO
From $591 per night (USD)
VRBO
Crystal Sands Unit 806 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unbelievable Beach Views - Just Walk Downstairs to Your White Sand Paradise Enjoy a view of world famous Siesta Key th ...
From $591 per night (USD)
VRBO
From $517 per night (USD)
Expedia
Crystal Sands Villa 13 - Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
For more privacy we offer you this 2 bedroom 2 bath villa flanking our attractive palm lined boulevard and steps from ou ...
From $517 per night (USD)
Expedia
From $476 per night (USD)
VRBO
Crystal Sands Tower Unit 203 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $476 per night (USD)
VRBO
From $483 per night (USD)
Expedia
Crystal Sands Tower Unit 805 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $483 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Crystal Sands Villa 17 - Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
For more privacy we offer you this 2 bedroom 2 bath villa flanking our attractive palm lined boulevard. Gracious living ...
From $445 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Crystal Sands Tower Unit 307 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A luxurious two-bedroom, two bath unit beautifully redecorated! Sit and relax on the lanai and enjoy the spectacular vi ...
From $474 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Condo# 204 2 Bedroom 1 Bath condo is steps to the white powdered sand of Siesta Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Here at La Siesta Condominiums you also have easy access to Siesta Village and it's numerous restaurants, specialty shop ...
From $279 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Crystal Sands Tower Unit 1204 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $479 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Crystal Sands Tower Unit 1004 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Affectionately called "The Perch", unit #1004 has been in our family since the building was nothing more than a blueprin ...
From $481 per night (USD)
VRBO
From $694 per night (USD)
Expedia
Crystal Sands Tower Unit 404 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Breathtaking Views - Beachfront Condo - Completely Renovated Enjoy breathtaking views of the Gulf of Mexico and world-f ...
From $694 per night (USD)
Expedia
From $484 per night (USD)
VRBO
Crystal Sands Tower Unit 305 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Treat yourself to a completely remodeled and updated 3rd floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...
From $484 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Crystal Sands Tower Unit 502 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SONG OF SIESTA KEY!! Located on Beautiful #1 Award Winning White Sands of Siesta Key Beach with panoramic views from 30 ...
From $481 per night (USD)
Expedia
From $477 per night (USD)
VRBO
Crystal Sands Tower Unit 506 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Treat yourself to a completely remodeled and updated 5th floor 2 bedroom 2 bath ocean front condo. Enjoy the beautiful ...
From $477 per night (USD)
VRBO
From $480 per night (USD)
Expedia
Crystal Sands Tower Unit 704 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the best of Crystal Sands in this beachy, contemporary 2-bedroom, 2 bath condo overlooking the 2011 and 2017 Best ...
From $480 per night (USD)
Expedia
From $486 per night (USD)
VRBO
Crystal Sands Tower Unit 710 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $486 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Crystal Sands Villa 20 - Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
For more privacy we offer you this 2 bedroom 2 bath villa flanking our attractive palm lined boulevard. Gracious living ...
From $445 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Crystal Sands Tower Unit 205 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Crystal Sands Condominiums! We would love to have you stay with us in one of our luxury 2-bedroom 2-bath full ...
From $481 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Condo # 111 Luxurious Living by Siesta Beach in this renovated 2b/1b ground floor unit
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
NOW WITH PRIVATE WiFi. Our condo is beautifully decorated with elegant touch & taste. It was recently renovated with st ...
From $280 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Coastal Getaway minutes from Siesta Key, America’s #1 Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Set back off the road on a quiet lane, enjoy this newly furnished, cozy modern coastal home. With this 3 bedroom, 2 bat ...
From $325 per night (USD)
VRBO
From $257 per night (USD)
Expedia
Condo# 319 Located across the street from Siesta Key Beach, Gulf and Pool View Condo!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
** This unit offers reservations with a 4-night minimum from April/11/2026 through December/11/26 and April/10/27 throu ...
From $257 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Condo# 308 Modern Siesta Key 2BR Condo – Steps from the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
SPECIAL!!! 10% OFF ANY DATE FROM NOW TO DECEMBER 2026, IF YOU BOOK BY MARCH 1, 2026!!!! ** This unit offers reservat ...
From $280 per night (USD)
VRBO
$Condo# 208 Charming Condo at La Siesta with Partial Beach Views \Your home away from home\$
From $237 per night (USD)
Expedia
Condo# 208 Charming Condo at La Siesta with Partial Beach Views \"Your home away from home\"
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
SPECIAL 20% DISCOUNT ON NEW RESERVATIONS MADE MAY 1ST THROUGH DECEMBER 1ST, 2026!! ** This unit offers reservations w ...
From $237 per night (USD)
Expedia
From $271 per night (USD)
VRBO
1/2 Mi to Beach! Siesta Key Home w/ Lanai
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Community Pool Access | Private Deck w/ Bay Views | 2 Beach Chairs Provided Begin your sun-kissed adventures at this 2- ...
From $271 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Condo #311 Extraordinary Siesta Key Beach View at La Siesta- fully renovated!,**20% off July,Aug,Sept,Oct Reservations
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
** 20% RENTAL RATE DISCOUNT FOR RESERVATIONS MADE JULY THROUGH OCTOBER 2026** ** This unit offers reservations with a 4- ...
From $280 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Palm Bay Club Bayside | Resort Pools, Hot Tub & Private Beach on Siesta Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up to sunrise over the bay, walk across the street to Siesta Key's #1-rated beach, then spend the afternoon between ...
From $325 per night (USD)
VRBO
From $1208 per night (USD)
Expedia
🌴 Villa Vista Mare | Gulf Views, Semi-Private Pool + Steps to Siesta Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🌴 Villa Vista Mare | Gulf Views, Semi-Private Pool + Steps to Siesta Beach 💖 Why You'll Love This Home Wake up to swe ...
From $1208 per night (USD)
Expedia
From $236 per night (USD)
VRBO
Beach Condo on Siesta Key Beach w/ Heated Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
If you are going to visit the #1 beach in the country, then stay on the #1 beach! This two bedroom, two full bathroom be ...
From $236 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
On Siesta Key, The ‘pool view’ overlooks the swimming pool & has a private covered open porch for shade 1 bed 1 bath w/ ...
From $308 per night (USD)
Expedia
From $977 per night (USD)
VRBO
🌴 Crescent Cottage | Private Pool, Pet Friendly, Walk to Crescent Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
🌴 Crescent Cottage | Private Pool, Pet Friendly, Walk to Crescent Beach 💖 Why You'll Love This Home Just 0.2 miles fr ...
From $977 per night (USD)
VRBO
From $724 per night (USD)
Expedia
Sand Dollar Cottage | Waterfront Home w/ Private Pool & Kayaks! Minutes to Siesta Key Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
🌴 Sand Dollar Cottage | Canal-Front Oasis + Private Heated Pool 💖 Why You'll Love This Home Float into coastal sereni ...
From $724 per night (USD)
Expedia
From $1241 per night (USD)
VRBO
Villa Champagne | Pet Friendly Waterfront Home w/ Private Pool & Spa, Close to Beach & Village!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
🌴 Villa Champagne | Private Pool, Walk to Siesta Key Beach and Island Living 💖 Why You'll Love This Home Wake up to c ...
From $1241 per night (USD)
VRBO
From $1486 per night (USD)
Expedia
Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w/ Private Pool, Short Walk to Beach
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
🌴 Sandy Seahorse Cottage | Sleeps 16 + Heated Pool + Walk to Crescent Beach 💖 Why You'll Love This Home Perfectly des ...
From $1486 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Updated and clean, two heated pool, tennis, and beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Enjoy this updated townhome within walking distance to Siesta Key's main beach. The property is located within a resort ...
From $354 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Enjoy the Siesta Key Beach Life to the fullest! Beach AND Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*** NEW *** Siesta Key beach has become known world wide for its incredible miles of soft white sand beaches and small v ...
From $254 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Waterfront Pool Home - Amazing Sunsets Included
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
There are so many beautiful neighborhoods tucked away in quiet communities along the keys and the entire Florida coast a ...
From $395 per night (USD)
VRBO
From $380 per night (USD)
Expedia
Walk to the Beach & Village, Heated Pool Oasis, Spacious
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover your dream vacation rental in the heart of Siesta Key, Florida, where coastal charm meets modern luxury. This s ...
From $380 per night (USD)
Expedia
From $400 per night (USD)
VRBO
The Coral Cottage close to all that Sarasota has to offer
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
We are Matt and Val, and we purchased this home with a vision to create a warm, inviting space for individuals, couples ...
From $400 per night (USD)
VRBO
From $359 per night (USD)
Expedia
Hidden Paradise Among Tropical Landscape on Lakefront Property on Siesta Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and roll-a-ways available on ...
From $359 per night (USD)
Expedia
From $359 per night (USD)
VRBO
Lakeside Hidden Paradise Among Tropical Landscape W/ Heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled along the serene waters of Heron Lagoon, our 1-bedroom suites at Siesta Heron Suites & Villas offer the perfect ...
From $359 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Spending time in sunny Siesta Key is always a treat for travelers. Those looking to enhance their stay with the inclusio ...
From $331 per night (USD)
Expedia
From $295 per night (USD)
VRBO
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
There's nothing more refreshing than knowing you get to spend time in sunny Siesta Key. When you have a trip on the cale ...
From $295 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Great place to see the dolphins! And less than half a mile from Turtle Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sunrise Bay is a 2BR, 1.5 bath, second floor apartment, in a 4-plex apartment property. It faces east and is on the wat ...
From $310 per night (USD)
Expedia
From $216 per night (USD)
VRBO
VILLA 5, Siesta Key, Pool View. King Bed. Daily rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Villa 5 King Bed Ground Floor, Studio Suite, Shared Pool, 2 minutes walk to the Crescent Beach Access #13 from your doo ...
From $216 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Siesta Key For Me @ The Palm Bay Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly Renovated Siesta Key Condo | Ocean & Bay Views | Sleeps 6 | The Palm Bay Club Exciting Updates May 2025! Our condo ...
From $430 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Adorable Lido Beach Home- walk to beach and St. Armand's
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy a morning stroll on the beach collecting sea shells, walk to St. Armand's to experience great restaurants and shop ...
From $446 per night (USD)
VRBO
From $211 per night (USD)
Expedia
Sea Side Vacation Home - By 5 beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our remodeled Tropical Vacation Home has everything for your living needs. 3 Bedroom with Office/Den. We are only 5 mi ...
From $211 per night (USD)
Expedia
From $1067 per night (USD)
VRBO
🌴 Casa Eulimia | Private Heated Pool, Walk to Crescent Beach, Pet Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
🌴 Casa Eulimia | Private Heated Pool, Walk to Crescent Beach, Pet Friendly 💖 Why You'll Love This Home Just a short s ...
From $1067 per night (USD)
VRBO
From $752 per night (USD)
Expedia
Seahorse Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
🌴 Seahorse Cabana | Heated Pool + 2-Min Walk to Crescent Beach 💖 Why You'll Love This Home Just steps from the powder ...
From $752 per night (USD)
Expedia
From $1189 per night (USD)
VRBO
Casa Ohana | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Casa Ohana | Private Heated Pool + Steps to Siesta Key Beach 💖 Why You'll Love This Home Imagine waking up in a coasta ...
From $1189 per night (USD)
VRBO
From $1170 per night (USD)
Expedia
Casa Tegula | Pet Friendly 🐶 Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
🌴 Casa Tegula | Elevated Views + Heated Pool Near Beach 💖 Why You'll Love This Home Perched on the top floor with tr ...
From $1170 per night (USD)
Expedia
From $1183 per night (USD)
VRBO
🌴 Casa Antilles | Pet Friendly, Ping Pong Table, Private Pool, Steps to Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
🌴 Casa Antilles | Pet Friendly, Ping Pong Table, Private Pool, Steps to Beach 💖 Why You'll Love This Home Step into s ...
From $1183 per night (USD)
VRBO
From $1067 per night (USD)
Expedia
Casa Junonia | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to Casa Junonia, a gorgeous vacation rental duplex located on the Southern end of Siesta Key. This spacious and ...
From $1067 per night (USD)
Expedia
From $480 per night (USD)
VRBO
🌴 Casita Mar | Steps to Crescent Beach, HOA Pool & Quiet Island Living on Siesta Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
🌴 Casita Mar | Steps to Crescent Beach, HOA Pool & Quiet Island Living on Siesta Key 💖 Why You'll Love This Home Casi ...
From $480 per night (USD)
VRBO
From $1052 per night (USD)
Expedia
Admirals Watch | Ocean Views from Spacious Balconies, Heated Pool, and Steps to Siesta Key Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🌴 Admiral's Watch | Gulf Views + Steps to Siesta Key Beach 💖 Why You'll Love This Home From the moment you step insid ...
From $1052 per night (USD)
Expedia
From $963 per night (USD)
VRBO
La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
"🌴 La Contento Casa | Private Heated Pool, Walk to Siesta Key Village and Beach 💖 Why You'll Love This Home Awaken to ...
From $963 per night (USD)
VRBO
From $1717 per night (USD)
Expedia
The Solaster | Pet Friendly Home on Siesta Key w/ 2 Heated Pools, Walk to Beach & South Village!
Bedrooms:
6
Bathrooms:
6
Sleeps:
20
🌴 Solastar | A Luxury Island Escape, 2 Private Pools + 3-Min Walk to Crescent Beach 💖 Why You'll Love This Home The S ...
From $1717 per night (USD)
Expedia
From $2194 per night (USD)
VRBO
The Abalone | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
8
Sleeps:
24
Welcome to The Abalone, a gorgeous vacation rental duplex located on the Southern end of Siesta Key. This spacious and a ...
From $2194 per night (USD)
VRBO
From $798 per night (USD)
Expedia
🏖️ Peacock Villa | Semi-Private Pool, Steps to Siesta Beach, Cabana Room
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🏖️ Peacock Villa | Semi-Private Pool, Steps to Siesta Beach, Cabana Room 💖 Why You'll Love This Home Step into coasta ...
From $798 per night (USD)
Expedia
From $1152 per night (USD)
VRBO
Casa Coquina | Pet Friendly, Ping Pong Table, Private Pool, Steps to Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
🌴 Casa Coquina | Pet Friendly, Ping Pong Table, Private Pool, Steps to Beach 💖 Why You'll Love This Home Step into co ...
From $1152 per night (USD)
VRBO
From $2420 per night (USD)
Expedia
The Nautilus | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
8
Sleeps:
24
🌴 The Nautilus | 2 Heated Pools + Walk to Crescent Beach 💖 Why You'll Love This Home Welcome to The Nautilus—an expa ...
From $2420 per night (USD)
Expedia
From $898 per night (USD)
VRBO
Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
🌴 Casita Sun Star | A Siesta Key Gem with Private Pool + Walk to Beach & Village 💖 Why You'll Love This Home Casita ...
From $898 per night (USD)
VRBO
From $1627 per night (USD)
Expedia
🦋 Casa De Mariposa | Heated Pool, Gulf Views, Dual-Villa Duplex, Walk to Siesta Key Beach
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
🦋 Casa De Mariposa | Heated Pool, Gulf Views, Dual-Villa Duplex, Walk to Siesta Key Beach 💖 Why You'll Love This Home ...
From $1627 per night (USD)
Expedia
From $964 per night (USD)
VRBO
🌴 Sol Y Mar | Private Duplex - Two Casitas, Walk to Siesta Keys Crescent Beach, HOA Pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
🌴 Sol Y Mar | Private Duplex - Two Casitas, One Island Escape, Walk to Siesta Key's Crescent Beach, HOA Pool 💖 Why Yo ...
From $964 per night (USD)
VRBO
From $483 per night (USD)
Expedia
🌴 Casita Sol | Walk to Crescent Beach, HOA Pool & Easy Island Living on Siesta Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
🌴 Casita Sol | Walk to Crescent Beach, HOA Pool & Easy Island Living on Siesta Key 💖 Why You'll Love This Home Casita ...
From $483 per night (USD)
Expedia
From $1306 per night (USD)
VRBO
Casa Mahalo | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Casa Mahalo | Top-Floor Luxe Retreat Steps from Siesta Key Beach 💖 Why You'll Love This Home Perched high above the pa ...
From $1306 per night (USD)
VRBO
From $753 per night (USD)
Expedia
Sandy Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
🌴 Sandy Cabana | Heated Pool + Walk to Crescent Beach 💖 Why You'll Love This Home Tucked away on a quiet South Siesta ...
From $753 per night (USD)
Expedia
From $3247 per night (USD)
VRBO
The Big Kahuna | SK Village, Pet Friendly, 2 Heated Pools, Elevator, Ping Pong Tables Steps to Beach
Bedrooms:
6
Bathrooms:
8
Sleeps:
24
🌺 The Big Kahuna | Two Luxe Villas + Double the Fun Steps from Siesta Key Beach 💖 Why You'll Love This Home More spac ...
From $3247 per night (USD)
VRBO
From $1073 per night (USD)
Expedia
🌴 Serenity Cottage | Multilevel Home on Siesta Key w/ Private Pool & Spa, Short Walk to Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🌴 Serenity Cottage | Heated Pool & Spa + 2‑min Walk to Crescent Beach 💖 Why You'll Love This Home Sunlight fills ever ...
From $1073 per night (USD)
Expedia
From $2347 per night (USD)
VRBO
The Conch | Luxury Pet Friendly Home, 2 Heated Pools, Ping Pong Tables Steps to Beach!
Bedrooms:
6
Bathrooms:
8
Sleeps:
26
🌴 The Conch | 2 Heated Pools + Steps to Crescent Beach 💖 Why You'll Love This Home Step into The Conch, a rare Siesta ...
From $2347 per night (USD)
VRBO
From $1139 per night (USD)
Expedia
🌴 Casa Stolida | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
🌴 Casa Stolida | Pet Friendly, Ping Pong Table, Private Heated Pool, Steps to Beach! 💖 Why You'll Love This Home Step ...
From $1139 per night (USD)
Expedia
From $887 per night (USD)
VRBO
Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
🌴 Casita Morning Star | A Coastal Charm with Private Pool, Walk to Crescent Beach + Village 💖 Why You'll Love This Ho ...
From $887 per night (USD)
VRBO
From $798 per night (USD)
Expedia
🦋 Monarch Villa | Semi Private Pool, Gulf Views, Private Cabana Room, Steps to Siesta Key Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
🦋 Monarch Villa | Semi Private Pool, Gulf Views, Private Cabana Room, Steps to Siesta Key Beach 💖 Why You'll Love Thi ...
From $798 per night (USD)
Expedia
From $1226 per night (USD)
VRBO
Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
🌴 Topsail Cottage | Gulf Views + Walk to Crescent Beach 💖 Why You'll Love This Home Wake up to sea breezes and panora ...
From $1226 per night (USD)
VRBO
From $955 per night (USD)
Expedia
The Lookout - 891 “Siesta Key’
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
KEEP READING BELOW! THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME AND CONTAINS VERY USEFUL INFORMATION THAT YOU WON’T ...
From $955 per night (USD)
Expedia
From $536 per night (USD)
VRBO
Beachfront Home on Gulf of Mexico w/ Indoor Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Pack your bags for a lavish getaway and stay at this chic oceanfront vacation rental in Englewood! Resting on a stunning ...
From $536 per night (USD)
VRBO
From $590 per night (USD)
Expedia
Crystal Sands Tower Unit 903 - Beachfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Breathtaking, unobstructed, North to South, panoramic views of the Gulf of Mexico on renowned Crescent Beach; located o ...
From $590 per night (USD)
Expedia
From $693 per night (USD)
VRBO
⭐️ Pool & Gulf Views, 2BR + Den, Prime Siesta Key Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cozy Coastal Getaway Beautifully updated 2BR + den, 2BA apartment (1,200 sqft) on the first floor with 2 private balco ...
From $693 per night (USD)
VRBO
From $793 per night (USD)
Expedia
Beautiful West of The Trail Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Exquisite West of Trail home in Granada is a quiet, private neighborhood with easy access to all amenities. 4 Bedrooms 3 ...
From $793 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Luxury Beach Condo on Crescent Beach #1 Beach in USA
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover your perfect vacation at Crescent Siesta Key. Located directly on the beautiful sands of Crescent Beach, this ...
From $430 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Walk to Beach: Resort-Style Siesta Key Condo!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
2 Heated Community Outdoor Pools | Large Sunroom w/ Desk & Dining Area | 7 Mi to Downtown Sarasota | 1,600 Sq Ft Have f ...
From $251 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Family getaway 5 miles to Siesta Beach. Heated private Pool, bicycles.Sleep 10.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to our Blue Beach House! Look no further, you have found the ideal rental for relaxing in the Florida sun! This ...
From $524 per night (USD)
VRBO
From $427 per night (USD)
Expedia
Steps away from the #1 beach! Spectacular views on the GIANT balcony!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Jamaica Royale's private BEACH FRONT community is just steps away from the soft white quartz sand of Siesta Key Beach wh ...
From $427 per night (USD)
Expedia
From $294 per night (USD)
VRBO
Luxury condo steps away from Siesta Key public beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the Spacious Luxury - This welcoming and spacious townhouse-style condominium is located on the 8 mile-long barr ...
From $294 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Escape to this vibrant 3BR,Pet friendly Siesta Key retreat, just steps from pristine beaches and the lively Siesta Key V ...
From $509 per night (USD)
Expedia
From $114 per night (USD)
VRBO
2/2 Ground Unit 10 Min to beach on golf course
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Venice vacation rental ground floor condo has 2 bedrooms, 2 baths and room for 4 guests with air mattress. It featu ...
From $114 per night (USD)
VRBO
Click For Pricing
Expedia
2 Cottages Rented Together, Htd Pool, Near Beaches
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Bring your friends, family and loved ones to enjoy an unforgettable escape at this unique property which comfo ...
Click For Pricing
Expedia

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