
Sarasota Area Rentals
- From $229 per night (USD)
VRBO
14th floor condo heart of city ,overlooking bay .Available 3months or yearly !
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
It’s a beautiful 2 BR, 1 Bath corner unit with 270 degree view of the bay as well as city with one allocated parking o ...
From $229 per night (USD)VRBO
- From $330 per night (USD)
Expedia
Walk to Beach | Heated Pools | Highly Rated | Guest Favorite | Lanai | Tennis and Pickleball | Gym
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $330 per night (USD)Expedia
- From $190 per night (USD)
VRBO
Studio Apartment, Safe & Walkable area, Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Super cute, secure and private in downtown Sarasota. Queen sized bed and sofa with private bathroom/shower. Located abov ...
From $190 per night (USD)VRBO
- From $207 per night (USD)
VRBO
2 Bed w/ Private Pool on Canal/Cul-de-sac, minutes from the Beach, Dog friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This home is bright, open, airy, and clean - the perfect place to relax and unwind. The location is just 2.5 miles from ...
From $207 per night (USD)VRBO
- From $1127 per night (USD)
VRBO
Isla Amor | Escape to a Luxury Waterfront Home with Heated Pool & Stunning Views in Siesta Key
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
🌴 Isla Amor | Waterfront Oasis + 0.3 Miles to Siesta Key Beach 💖 Why You'll Love This Home Imagine waking up to serene ...
From $1127 per night (USD)VRBO
- From $290 per night (USD)
Expedia
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and fa ...
From $290 per night (USD)Expedia
- From $312 per night (USD)
VRBO
\"Discover Your Coastal Oasis in Longboat Key, FL\" and St. Armands Area
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stunning one bedroom one bath unit with just a short walk to Longboat Key Beach(Across the Street). Come enjoy beautiful ...
From $312 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Happy Clam has just undergone a significant makeover and upgrade. It is better than ever! Absolutely, amazing condo i ...
From $321 per night (USD)Expedia
- From $146 per night (USD)
VRBO
3-bedroom vacation cottage, 2 min drive to Nokomis Beach/ Gulf of Mexico beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Our remodeled and chic beach cottage is close to Casey Key Public Beach (3/4 of a mile), 9 minutes from Venice Beach. O ...
From $146 per night (USD)VRBO
- From $264 per night (USD)
Expedia
Condo #104 Completely remodeled Siesta Key 2 bedroom 1 bath Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 Bedroom, One Bath Condo is just steps to the white, powered sugar sand of Siesta Key. We have easy access to Sies ...
From $264 per night (USD)Expedia
- From $595 per night (USD)
VRBO
Gertrude's Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Casa Tranquilla Spacious luxury home, 100% private, just 100ft from best views on Siesta Key. Impeccable 2025 remodel a ...
From $595 per night (USD)VRBO
- From $314 per night (USD)
Expedia
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Vacation rental home in Englewood / South Venice, Florida. The house is literally a short walk from the beach. It was co ...
From $314 per night (USD)Expedia
- From $384 per night (USD)
VRBO
Walk to Lido Beach, Walk to Armand Cir with Dining & Shopping, WiFi, Xfinity, 2TV's, Heated Pool/Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $384 per night (USD)VRBO
- From $243 per night (USD)
Expedia
Lido Beach and St. Armand's Circle at your Footsteps.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sarasota Certificate of Registration # VR22-00027 Minimum 7 night stay Beautiful, roomy, sunny 2BR, 2 BA old style Flori ...
From $243 per night (USD)Expedia
- From $160 per night (USD)
VRBO
Newly renovated only minutes away from the beach!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This beautiful and completely remodeled cottage retreat has all the comfort you will need for your next vacation! Fully ...
From $160 per night (USD)VRBO
- From $699 per night (USD)
Expedia
Casa Leone | Pet Friendly 🐶 on Siesta Key w/ Private Heated Pool, Golf Cart, & Putting Green!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Unparalleled Luxury at Casa Leone, Siesta Key's Hidden Gem Welcome to Casa Leone, your ultimate luxury getaway on Siesta ...
From $699 per night (USD)Expedia
- From $141 per night (USD)
VRBO
Newly Decorated with Pool Views! Convenient Access-no stairs!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Lots of room for you and your guests. New carpeting in the bedrooms, fresh paint, plantation shutters, beautiful tile fl ...
From $141 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Downtown,Italian Villa For Two,Resort Style.5 minutes to Siesta-Lido.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Please Read the entire descriptions and additional information about our propriety. A spacious space to relax for two. ...
From $270 per night (USD)Expedia
- From $254 per night (USD)
VRBO
Water Front on Turtle Lagoon. Minutes from Turtle Beach & Siesta Key Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
*** UPDATE January 2025 - We recently did a major update to our property. We addressed all issues from our previous gu ...
From $254 per night (USD)VRBO
- From $690 per night (USD)
Expedia
Steps to Siesta Key Beach / Charming 2-Bedr + den apartment with Patio & Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just Steps from Siesta Key Beach – Charming 2-Bedroom Apartment with Patios & Pool Only 60 steps from the stunning Sies ...
From $690 per night (USD)Expedia
- From $289 per night (USD)
VRBO
Siesta Key Bungalows: Coquina Bungalows
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful courtyard bungalow has a queen bed, sleeper sofa & full kitchen with cable TV. This property is close t ...
From $289 per night (USD)VRBO
- Click For Pricing
Expedia
Beachfront Resort Style Living - Siesta Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
**NEWLY REMODELED KITCHEN -- UPDATED FLOORS AND BATHROOMS** Come enjoy luxurious resort style living in this beautiful t ...
Click For PricingExpedia
- From $489 per night (USD)
VRBO
Island House Beach Resort 18S
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This beautifully appointed 1 bedroom, 2 bathroom features a primary ensuite with a king bed and a sofa sleeper. The unit ...
From $489 per night (USD)VRBO
- From $308 per night (USD)
Expedia
Cozy cottage on Casey Key
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautifully decorated 1 bedroom 1 bath bay side condo with private beach access. Full kitchen and dining bar with barsto ...
From $308 per night (USD)Expedia
- From $348 per night (USD)
VRBO
The Beach Club at Siesta Key #106A Resort by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $348 per night (USD)VRBO
- From $327 per night (USD)
Expedia
Turquoise Water & Soft White Sand - The Beach Club at Siesta Key #104A by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $327 per night (USD)Expedia
- From $499 per night (USD)
VRBO
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $499 per night (USD)VRBO
- From $564 per night (USD)
Expedia
Bright & Modern ~ Heated Pool ~ Gated Beach ~ Pkg!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Experience the modern design and relaxing comfort of this newly renovated 2BR 2Bath quadplex unit, just a few mins from ...
From $564 per night (USD)Expedia
- From $494 per night (USD)
VRBO
Blue Seas & White Sand 2BR-The Beach Club at Siesta Key #200C Resort by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $494 per night (USD)VRBO
- From $323 per night (USD)
Expedia
Steps to Siesta Key beach, restaurants and shops!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Overlooking the large, heated pool and just a few steps to the famous white sands of Siesta Key Beach, Unit 410 is an is ...
From $323 per night (USD)Expedia
- From $847 per night (USD)
VRBO
Newly Renovated Large 4BR w/ Pool - Walk to Gated beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Newly renovated gated beach access apartment with a pool. This is a four bedroom and two bath apartment that makes up on ...
From $847 per night (USD)VRBO
- From $347 per night (USD)
Expedia
On Siesta Key Beach - no streets to cross! Large, heated pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You don’t have to cross any streets to get to Siesta Key Beach from this beautiful two-bedroom, two-bath condo! This new ...
From $347 per night (USD)Expedia
- From $525 per night (USD)
VRBO
Beachfront Luxury Condo. Best View on Siesta Key Beach - no streets to cross!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Make your next vacation one to remember forever by booking a stay in the Sea Shell Penthouse Condo. This beachfront cond ...
From $525 per night (USD)VRBO
- From $421 per night (USD)
Expedia
2-BR Suite Close to Beach w Trolley-The Beach Club at Siesta Key #204B by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $421 per night (USD)Expedia
- From $247 per night (USD)
VRBO
St. Armands oasis with saltwater pool - walk to beach & shops
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Anything Is Possible Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $247 per night (USD)VRBO
- From $407 per night (USD)
Expedia
First Lido - 3rd floor unit\nNOTE: DUE TO HURRICANES, ELEVATOR IS UNDER REPAIRS
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Beach front - Full view of the Gulf of Mexico. Fully furnished and equiped. Includes Long Distance phone service within ...
From $407 per night (USD)Expedia
- From $689 per night (USD)
VRBO
Coral Breeze | Pet Friendly Home, Heated Pool & Spa, Minutes to Village and Siesta Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
🌴 Coral Breeze | Private Pool + Walk to Siesta Key Village 💖 Why You'll Love This Home Sunshine, swaying palms, and ...
From $689 per night (USD)VRBO
- From $347 per night (USD)
Expedia
Spacious 2BR Close to World-Famous Sand Beach Club at Siesta Key #102A by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Beach Club at Siesta Key by RVA Resort Vacations – Your Coastal Escape Awaits Discover the breathtaking beauty of ...
From $347 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Tropical Waters & Magical Sunsets-The Beach Club at Siesta Key #106B by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $354 per night (USD)VRBO
- From $277 per night (USD)
Expedia
Beautiful newly decorated and furnished private home. Fits any personality!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious home. Large open concept with lots of sunlight. Split home so master bedroom on other side with private bath. W ...
From $277 per night (USD)Expedia
- From $224 per night (USD)
VRBO
Updated Spacious. 5 Min to Manasota Beach. Loaded w/amenities. Pets Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Thank you for taking a moment to view one of out vacation home brough to you by Sandy Flamingo Vacations. This home is ...
From $224 per night (USD)VRBO
- From $1297 per night (USD)
Expedia
Gertrude's Siesta | 4-min Walk to Beach & Village, Tropical & 100% Private!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 22
Casa Van Lopik 100% Private 6BR duplex in the Siesta Key Village, 4-min walk to best beaches shopping dining and enterta ...
From $1297 per night (USD)Expedia
- From $1200 per night (USD)
VRBO
Gertrudes Siesta Village Properties - short walk to Siesta's best beaches!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Gertrude's Village Properties Two properties in the top location on the island with 4 patios and private gate into world ...
From $1200 per night (USD)VRBO
- From $486 per night (USD)
Expedia
Stunning Gulf Views From Horizons West #704, a 2B, 2B on Siesta Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located in the centre of the high rise on the 7th floor, the views from the lanai are directly to the garden, pool, the ...
From $486 per night (USD)Expedia
- From $516 per night (USD)
VRBO
Pristine Gulf Waters & Location-The Beach Club at Siesta Key #108D by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $516 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Amazing Villa with Extra Large Heated Pool ! 50% off Regular Rates!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
If you are looking for a luxurious and serene holiday in the sun, then look no further. Our spacious and beautiful Flor ...
From $287 per night (USD)Expedia
- From $387 per night (USD)
VRBO
The Casa Coco | Garden : Modern and relaxing home with heated pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you see a gap in our calendar you are interested in send us an inquiry. If your dates are not available Check our ot ...
From $387 per night (USD)VRBO
- From $331 per night (USD)
Expedia
Breathtaking Turquoise Gulf Water-The Beach Club at Siesta Key #104D by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $331 per night (USD)Expedia
- From $4514 per night (USD)
VRBO
Rare private beachfront estate on Gulf of Mexico.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Wake up in the morning and go for a walk along the beautiful sandy beach. The beach is incredible. Very rare and private ...
From $4514 per night (USD)VRBO
- From $302 per night (USD)
Expedia
Beachplace 7-404 Condo by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
RVA presents a delightful two-bedroom, two-bathroom unit at Beachplace, featuring a king-sized master bedroom and two tw ...
From $302 per night (USD)Expedia
- From $260 per night (USD)
VRBO
Adorable Beach Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful Venice Island Home is less that 1 mile to Venice Beach. Just think you can have the beach life this wint ...
From $260 per night (USD)VRBO
- From $565 per night (USD)
Expedia
At Sun Sea Terrace | Luxury Siesta Key Condo w/ Heated Pool, Short Walk to Beach and Village!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
🌴 At Sun Sea Terrace | Rooftop Views + Steps to Siesta Beach & Village 💖 Why You'll Love This Home Start your morning ...
From $565 per night (USD)Expedia
- From $764 per night (USD)
VRBO
Hidden Treasure | Located on Siesta Key w/ Private Heated Pool/Hot Tub & Spacious Outdoor Area
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to Siesta Key's Hidden Treasure – A Peaceful, Private Island Retreat Welcome to Siesta Key's Hidden Treasure, a ...
From $764 per night (USD)VRBO
- From $373 per night (USD)
Expedia
Location! Location! Location! Steps to Siesta Key Beach and many shops!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bright and inviting, this 2 bedroom, 2 bath condo has to be experienced to be believed! Located just steps from the famo ...
From $373 per night (USD)Expedia
- From $328 per night (USD)
VRBO
Heated Pool in Luxurious home, 3 minutes to beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
High End Spacious Home in the best laid back part of Florida's Gulf coast. Right on the border between Venice and Englew ...
From $328 per night (USD)VRBO
- From $278 per night (USD)
Expedia
Condo# 119 Beautifull updated Condo Siesta Key
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This unit has private WIFI and is appointed in cheerful clean modern decor and the patio opens just steps to the pool. T ...
From $278 per night (USD)Expedia
- From $168 per night (USD)
VRBO
*** Downtown Bungalow ***Beaches / Restaurants / Cafes***Just Minutes away!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This charming cottage is the perfect place for your stay in downtown Sarasota. The space: This two bedroom home has ...
From $168 per night (USD)VRBO
- From $467 per night (USD)
Expedia
Best location on Siesta Key/Crescent Beach - just steps to the water!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful two-bedroom condo is located just steps from the world-famous white sands of Siesta Key Beach. That mean ...
From $467 per night (USD)Expedia
- From $1864 per night (USD)
VRBO
The Hummingbird | Located in Siesta Key Village w/ Private Pool, Walk to Beach!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 20
The Hummingbird | 6BR/6BA | Sleeps 20 | Private Heated Pool | Heart of Siesta Key Village 🌴 Why You'll Love This Home ...
From $1864 per night (USD)VRBO
- From $420 per night (USD)
Expedia
\"Updated & Charming Pool Home 1 Mile from Siesta Key \"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our beautifully updated 3-bedroom, 2-bathroom single-family pool home, just 1 mile from the Siesta Key North ...
From $420 per night (USD)Expedia
- From $436 per night (USD)
VRBO
\"Safe & Clean\" Honeymoon Suite, - only 60 steps to the Siesta Key Public Beach -
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Only 60 steps to the beach. Entire apartment refurbished and updated incl. new flooring 2020. Spacious 1 bedroom / 2 f ...
From $436 per night (USD)VRBO
- From $210 per night (USD)
Expedia
2bed 2 bath sleeps 5 .. 3 smart TVs.. fully refurbished Very Close to the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
RENOVATED 2025 2 BED, 2 BATH CONDO 1st floor parking right outside WI-FI and smart tvs ...
From $210 per night (USD)Expedia
- From $436 per night (USD)
VRBO
Manasota Key Dream Beach House
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Perfect Get-Away Beach Home for Families! Sleeps 12 to 14, Heated Pool & Spa. This beautiful 5 bedroom, 4 bathroom beac ...
From $436 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Luxurious Living Steps to Lido Beach & Walking Distance to St. Armands Circle
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Freshly updated/painted condo with luxurious furnishings and steps to the Gulf of Mexico on exclusive Lido Key. This con ...
From $228 per night (USD)Expedia
- From $191 per night (USD)
VRBO
Amazing View - On Golf Course - Near Beaches, Shopping & Restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Highly sought after condo in Farmington Vistas. Newly furnished property perfect for extended vacation and/or leisure. ...
From $191 per night (USD)VRBO
- From $201 per night (USD)
Expedia
New Listing! Renovated End Unit, Pool/Bay Views, Heated Pool, Desk for Remote Work
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $201 per night (USD)Expedia
- From $245 per night (USD)
VRBO
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. SmartTV, Full Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Seahorse Shores - 409 Shore Road - Two Bedroom Beach Villa Located 1/2 Mile From Nokomis Beach and Casey Key. Gas grill ...
From $245 per night (USD)VRBO
- From $946 per night (USD)
Expedia
Honeysuckle | Located in Siesta Key Village w/ Heated Pool, Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
🌴 Honeysuckle | 3 King/Queen Bedrooms + Dual Kitchens | 0.2 Miles to Siesta Key Beach 💖 Why You'll Love This Home Hon ...
From $946 per night (USD)Expedia
- From $353 per night (USD)
VRBO
Siesta Key GULF SIDE~#100 - Peaceful Private Condo, 3 Pools, Jamaica Royale
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom, 2 bath tropical garden condo was completely renovated in the spring of 2025 ~ thanks to the floods of 20 ...
From $353 per night (USD)VRBO
- From $549 per night (USD)
Expedia
Siesta Key Pool House 3 Miles from the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The house is located within 10 minutes drive from both downtown and Siesta Keys beach, and about 20 minutes drive from L ...
From $549 per night (USD)Expedia
- From $187 per night (USD)
VRBO
Siesta Key Beach IDEAL LOCATION BEACH, VILLAGE, HEATED POOL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
2 week rental minimum from April through December. January, February March, are monthly rentals please select the first ...
From $187 per night (USD)VRBO
- From $386 per night (USD)
Expedia
The Casa Coco | Coronado: Updated home, Heated pool close to S. Venice beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you see a gap in our calendar you are interested in send us an inquiry. If your dates are not available Check our ot ...
From $386 per night (USD)Expedia
- From $409 per night (USD)
VRBO
Short walk to Private Access to Beach, 2 Pools, Gym, Clubhouse, Pond View, Ready to Book!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your saving ...
From $409 per night (USD)VRBO
- From $348 per night (USD)
Expedia
Resort-Style 2BR w Pool & Private Beach-Beach Club at Siesta Key #204C by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
RVA offers beautiful turquoise waters and quartz-crystal white sands, which have been officially ranked as the “finest, ...
From $348 per night (USD)Expedia
- From $427 per night (USD)
VRBO
Island House Beach Resort V35
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Island House Beach Resort- Siesta Key Florida, Crescent Beach - This lovely villa is located on the widest part of Cresc ...
From $427 per night (USD)VRBO
- Click For Pricing
Expedia
Quiet 1 B/B retreat minutes from the beach located in center of a bird sanctuary
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Enjoy the perks of a stylish upscale hotel minutes from the beach, steps from the Shamrock Nature Preserve Park and in t ...
Click For PricingExpedia
- From $241 per night (USD)
VRBO
Walk to the #1 Beach in America, Offers Heated community Pool, Free Wi-Fi
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Siesta Key has been named America's #1 beach time and time again. Experience fun in the sun like never before at this tw ...
From $241 per night (USD)VRBO
- From $553 per night (USD)
Expedia
Lantana | Located in Siesta Key Village w/ Heated Pool, Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
🌴 Lantana | Heated Pool + 0.2 Miles to Siesta Key Beach 💖 Why You'll Love This Home Slip into vacation mode at Lantan ...
From $553 per night (USD)Expedia
- From $916 per night (USD)
VRBO
Mandevilla | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
🌴 Mandevilla | 2 Balconies + 3 King Suites | 0.2 Miles to Siesta Key Beach 💖 Why You'll Love This Home Mandevilla com ...
From $916 per night (USD)VRBO
- From $364 per night (USD)
Expedia
Mimosa | Located in Siesta Key Village w/ Heated Pool and Just Steps to Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
"🌴 Mimosa | Heated Pool + 0.2 Miles to Siesta Key Beach 💖 Why You'll Love This Home Nestled just steps from Siesta Ke ...
From $364 per night (USD)Expedia
- From $730 per night (USD)
VRBO
Vinca | Great Location in Siesta Key Village w/ Heated Pool, Walk to Beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
🌴 Vinca | Top-Floor Hideaway + Balcony | 0.2 Miles to Siesta Key Beach 💖 Why You'll Love This Home Tucked just above ...
From $730 per night (USD)VRBO
- From $304 per night (USD)
Expedia
Modern Bright Contemporary Design 2,400 SF of comfort with Salt Pool & Spa, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in the vibrant landscape of Florida Sun Coast, this 2400-square-foot residence welcomes you with a perfect blen ...
From $304 per night (USD)Expedia
- From $221 per night (USD)
VRBO
Bright Home: Pool Access & Screened-In Porch!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Mixing resort amenities with homey surroundings, this vacation rental offers the best of both worlds. Stay at this 1-bed ...
From $221 per night (USD)VRBO
- From $1045 per night (USD)
Expedia
Pool, Putting Green, Steps to Shopping, & Tons of Living Space -The Shore House
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
The Shore House by Lido Key Vacations Sarasota FL 34236 Vacation Rental License #VR22-00033 Minimum stay duration of 7 ...
From $1045 per night (USD)Expedia
- From $276 per night (USD)
VRBO
Beautiful Vacation House Close to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2018 built 1750 sqft open space house in Venice East Neighborhood. Very quiet area. Grill and furniture on the patio and ...
From $276 per night (USD)VRBO
- From $262 per night (USD)
Expedia
Unit 103- Paradise Awaits
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to La Siesta 103! Newly renovated and completely furnished with an upscale beachy vibe. Enjoy your favorite be ...
From $262 per night (USD)Expedia
- From $281 per night (USD)
VRBO
Hidden Sandy cove walking distance to village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Florida charm awaits you just a short stroll to Siesta Key Village for shopping or casual and fine dining and a few minu ...
From $281 per night (USD)VRBO
- From $144 per night (USD)
VRBO
SUNNY PARADISE VACATION-GRAND PARADISO VENICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO SUNNY PARADISE VACATION RENTAL This beautiful, designer decorated 3 bedroom 2.5 bathroom townhouse is yours ...
From $144 per night (USD)VRBO
- From $97 per night (USD)
VRBO
~ Cozy In-law Apartment Close to Siesta Key ~
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
~ Cozy In-law Apartment Close to Siesta Key ~ . Cozy Private Apartment connected to our home, with a separate entrance a ...
From $97 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Paradise awaits!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Paradise awaits you! This spacious and recently renovated 2 bedroom and 2 bath condo is walking distance from Crescent b ...
From $180 per night (USD)Expedia
- From $437 per night (USD)
VRBO
Palm Paradise: Near Siesta Key Beach, Heated Salt Water Pool by Gulf Coast Holiday Homes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
SIESTA KEY PALM PARADISE is minutes away from the #1 beach in the US, with white quartz sand & the clear turquoise wate ...
From $437 per night (USD)VRBO
- From $136 per night (USD)
Expedia
Amazing View - On Golf Course - Top Floor - Near Beaches, Shopping & Restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This highly sought after and beautifully decorated 2 bedroom / 2 bath condo located in Farmington Vistas, which is a sma ...
From $136 per night (USD)Expedia
- From $137 per night (USD)
VRBO
Amazing View - 2 Bed 2 Bath Condo with Great Golf Course View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This highly sought after and beautifully decorated 2 bedroom / 2 bath condo located in Farmington Vistas, which is a sma ...
From $137 per night (USD)VRBO
- From $483 per night (USD)
Expedia
Plumbago | Prime Location in Siesta Key Village w/ Heated Pool, Walk to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
🌴 Plumbago | 2 King Suites + Balcony | 0.2 Miles to Siesta Key Beach 💖 Why You'll Love This Home Perched above Siesta ...
From $483 per night (USD)Expedia
- From $635 per night (USD)
VRBO
Private pool House with Fountains & Beach Walkable
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Great news! We've quickly reopened after Milton! Restaurants, stores, our beach access & Historic downtown-all now open! ...
From $635 per night (USD)VRBO
- From $154 per night (USD)
Expedia
Amazing View - On Golf Course - Near Beaches, Shopping & Restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This highly sought after and beautifully decorated 2 bedroom / 2 bath condo located in Farmington Vistas, which is a sma ...
From $154 per night (USD)Expedia
- From $848 per night (USD)
VRBO
Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
ROYAL PALM SUITE (sleeps 6 max), newly refurbished 3 bedroom luxury townhouse of sqft 1,850 over 3 floors, 2 kings and ...
From $848 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Beautifully renovated 1 Bedroom with Pool View/Inter-coastal, screened in Lanai
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
King in master, walk in shower, free wifi. Screened in patio off living room and bedroom for enjoying bay breezes with y ...
From $250 per night (USD)Expedia
- From $501 per night (USD)
VRBO
Island House Beach Resort 9S
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully appointed 2 bedroom, 2 bathroom features a primary ensuite with a king bed and the guest room features ...
From $501 per night (USD)VRBO
- From $252 per night (USD)
Expedia
Ocean View 1 Bedroom Condo on Siesta Key!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Condo #424 is located on the 4th floor at Harbor Towers Yacht & Racquet Club with a gulf view! This unit is a completel ...
From $252 per night (USD)Expedia




































































































