Sarasota Area Rentals
From $407 per night (USD)VRBO
Beautiful Apartment with first class amenities on The Anchorage, Siesta Key Apartment 1006
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1006. Welcome to this 2 bedroom 2 bathroom va ...
From $407 per night (USD)VRBO
From $450 per night (USD)Expedia
Luxury Contemporary Style Apartment on The Anchorage, Siesta Key Apartment 1001
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1001. Setting your travel sights on scenic Sie ...
From $450 per night (USD)Expedia
From $371 per night (USD)VRBO
Rent the Perfect 2 Bedroom Condo on The Anchorage, Siesta Key Condo 1002
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Condo 1002. If you’re the type of traveler that can’t w ...
From $371 per night (USD)VRBO
From $431 per night (USD)Expedia
Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
5 Star Villa Holidays is proud to present Siesta Key Apartment 1025. Your vacation begins as soon as you ste ...
From $431 per night (USD)Expedia
From $431 per night (USD)VRBO
Luxury Private Condo on The Anchorage, Siesta Key Condo 1024
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Condo 1024. In quaint Siesta Key you’ll find gorgeous b ...
From $431 per night (USD)VRBO
From $433 per night (USD)Expedia
Rent the Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1016
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1016. Warm natural light fills this home maki ...
From $433 per night (USD)Expedia
From $417 per night (USD)VRBO
Luxury 5 Star Apartment on The Anchorage, Siesta Key Apartment 1018
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1018. Bask in the ambiance of a true home whe ...
From $417 per night (USD)VRBO
From $418 per night (USD)Expedia
Beautiful Apartment with first class amenities on The Anchorage, Siesta Key Apartment 1019
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1019. Welcome to this pristine 2 bedroom, 2 b ...
From $418 per night (USD)Expedia
From $359 per night (USD)VRBO
Rent this Luxury 5 Star Apartment on The Anchorage, Siesta Key Apartment 1008
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1008. Bright colors and warm neutrals fill th ...
From $359 per night (USD)VRBO
From $417 per night (USD)Expedia
Rent the Perfect 2 Bedroom Apartment on The Anchorage, Siesta Key Apartment 1009
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
5 Star Villa Holidays is proud to present Siesta Key Apartment 1009. Just steps from the water and minutes f ...
From $417 per night (USD)Expedia
From $228 per night (USD)VRBO
Siesta Sol Bungalow, Relax by Siesta Key Beach 6 min drive in Gulf Gate Estates
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Siesta Sol Bungalow | Mid-Century Modern Retreat Near Beaches, Dining, and Entertainment Welcome to Siesta Sol Bungalow ...
From $228 per night (USD)VRBO
From $354 per night (USD)Expedia
Longboat Key Escape–Resort Pool + Ocean: Beachplace Condo # 7-102 by RVA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beachplace 7-102, a nicely decorated two-bedroom, two-bath unit at Beachplace that includes direct, private w ...
From $354 per night (USD)Expedia
From $976 per night (USD)VRBO
Private Gated Home in Siesta Village, Heated Pool & Pool Table - The Hideaway
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
The Hideaway by Siesta Key Luxury Rental Properties Welcome to The Hideaway, a luxurious private gated retreat featuri ...
From $976 per night (USD)VRBO
From $377 per night (USD)Expedia
Spacious 4bdr 3bath House with Heated Pool near Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious 4-bedroom, 3-bath home—perfect for families or groups looking to relax and unwind. Spend your evenings by the p ...
From $377 per night (USD)Expedia
From $114 per night (USD)VRBO
Lovely apartment 5 minutes to the beach, restaurants, shopping and services
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
<p>A short distance from sailing, windsurfing, and more, this pet-friendly apartment lets you experience it all. With th ...
From $114 per night (USD)VRBO
From $313 per night (USD)Expedia
Waterfront/Pool mins to Siesta Key Beach- bikes/kayaks/SUPs incl-paddle to beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
WATERFRONT PROPERTY - View the Gulf in our waterside rocking chairs and lanai!! Everything you need for a vacation or sh ...
From $313 per night (USD)Expedia
From $213 per night (USD)VRBO
Inviting Venice Home with Old Florida Charm Close to Everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to your Venice getaway! This spacious, comfortable home is the perfect base for enjoying everything the area has ...
From $213 per night (USD)VRBO
From $240 per night (USD)Expedia
Beautiful renovated 4th floor Condo across the street from Lido beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom 4th floor condo located on Lido Key (Sarasota). Enjoy beautiful walks, the beach and the nice pool/h ...
From $240 per night (USD)Expedia
From $314 per night (USD)VRBO
The Palm Bay club Siesta Key Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to b ...
From $314 per night (USD)VRBO
From $779 per night (USD)Expedia
Crystal Sands Tower Unit 1109 - Beachfront
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Unique... Highly desirable 4 bedroom unit in Crystal Sands on Siesta Key. Very rare 4 bedroom beachfront condo with a d ...
From $779 per night (USD)Expedia
From $523 per night (USD)VRBO
Endless Views | Walking Distance To Siesta Key Beach + Village w/ Rooftop Panoramic Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
🌴 Endless Views | Rooftop Balcony + 3-Min Walk to Siesta Key Beach 💖 Why You'll Love This Home Wake up to sweeping co ...
From $523 per night (USD)VRBO
From $215 per night (USD)VRBO
Updated,Sunny Cottage🌴near famous beaches🏝half mile to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Relaxing and charming 3 bedrooms, 2 bathrooms cottage walking distance /half mile/ to Main steet, Downtown, parks, resta ...
From $215 per night (USD)VRBO
From $295 per night (USD)VRBO
Grand Villa with Pool in Venice, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Dramatic two-story Tuscan-style villa in the heart of South Venice. You'll love the tall ceilings, stained glass window ...
From $295 per night (USD)VRBO
From $587 per night (USD)Expedia
2BR Healing Oasis w/Private Pool Near Sarasota Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
CERT #VR24-00175] Welcome to the Bohemian Bungalow! Spiritual Oasis! This is the perfect location for those who have a ...
From $587 per night (USD)Expedia
From $397 per night (USD)VRBO
Beachfront Condo at Siesta Breakers | Gulf Views | 2nd Floor | Renovated | Tennis & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Siesta Breakers on Crescent Beach! Escape to paradise on Siesta Key! This beautifully updated 2-bedroom, ...
From $397 per night (USD)VRBO
From $190 per night (USD)Expedia
Best Pool On the Gulf-Steps to the Crows Nest. Fall Openings!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Picture yourself relaxing on the couch, watching the boats go by, with all the natural light coming in through the skyli ...
From $190 per night (USD)Expedia
From $788 per night (USD)VRBO
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Super Private Beach Access (1 min walk- 100 feet from front door with private dock for fishing or Kayaking out the back ...
From $788 per night (USD)VRBO
From $556 per night (USD)Expedia
Bali Hai House | Canal-Front Home with Private Heated Pool, Near Siesta Key Village
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
🌴 Bali Hai House | Canal-Front Home with Private Heated Pool, Near Siesta Key Village 💖 Why You'll Love This Home Bal ...
From $556 per night (USD)Expedia
From $225 per night (USD)VRBO
Lido Beach Ocean View/POOL Sarasota Beachfront OFF SEASON RATES
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Lido Beach Spectacular Ocean View. St. Armands Circle. Close to many shops, resTaurants and entertainment. Deluxe unit ...
From $225 per night (USD)VRBO
From $165 per night (USD)Expedia
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 $165 per night (USD)Expedia
From $386 per night (USD)VRBO
Siesta Bayside 3BR Villa: Rare, Spacious Layout, Pickleball, Heated Pools, & Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Siesta Bayside 3 Bedroom Condo! This stunning second-story, 3-bedroom townhome in Siesta Bayside combine ...
From $386 per night (USD)VRBO
From $355 per night (USD)Expedia
Quaint Historic Apartment in Walkable Downtown #5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
My historic building was built in the 1950's and has clean character and ambiance. Walking distance to Whole Foods/Publi ...
From $355 per night (USD)Expedia
From $361 per night (USD)VRBO
Balcony Studio, Historic & Highly Walkable nestled between High-End Residential
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Super romantic, secure and private in the most desirable neighborhood downtown Sarasota. A Home away from Home - Close t ...
From $361 per night (USD)VRBO
From $202 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 $202 per night (USD)VRBO
From $1121 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 | Escape to a Luxury Waterfront Home with Heated Pool & Stunning Views in Siesta Key 💖 Why You'll Love Th ...
From $1121 per night (USD)VRBO
From $271 per night (USD)Expedia
Lido Beach Villa — Steps to the Beach & St. Armands.
- 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 $271 per night (USD)Expedia
From $381 per night (USD)VRBO
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 $381 per night (USD)VRBO
From $165 per night (USD)Expedia
Siesta Key 2 Bedroom Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Perfect little condo on siesta key, home of the #1 rated beach in the USA. Just minutes from the beaches and great rest ...
From $165 per night (USD)Expedia
From $152 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 $152 per night (USD)VRBO
From $392 per night (USD)Expedia
The President - 206 “Lido Key”
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
KEEP READING BELOW! THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME AND CONTAINS VERY USEFUL INFORMATION THAT YOU WON’T ...
From $392 per night (USD)Expedia
From $259 per night (USD)VRBO
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 $259 per night (USD)VRBO
From $354 per night (USD)Expedia
Gertrude 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 $354 per night (USD)Expedia
From $297 per night (USD)VRBO
Top Rated House For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to this spacious and beautifully modern 4-bedroom, 2-bath vacation home in the quiet Englewood / South Venice are ...
From $297 per night (USD)VRBO
From $229 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
Welcome to Kingston Arms 1st Floor! Simply paradise! This coveted end unit in Kingston Arms on Lido Key is just ste ...
From $229 per night (USD)VRBO
From $247 per night (USD)VRBO
Lido Beach and St. Armand's Circle at your Footsteps.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sarasota Certificate of Registration # VR22-00048 Minimum 7 night stay Beautiful, roomy, sunny 2BR, 2 BA old style Flori ...
From $247 per night (USD)VRBO
From $266 per night (USD)Expedia
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 $266 per night (USD)Expedia
From $187 per night (USD)VRBO
Lido Beach Gulf View Condo w/ pool. Right across from beach! ! OFF SEASON RATES
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Panoramic ocean View . 1bd, 1bth located immediately across for the beach. Right in the middle of Lido Beach. Close t ...
From $187 per night (USD)VRBO
From $519 per night (USD)Expedia
Casa Leone | Heated Pool & Spa, Pet Friendly, Putting Green
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Casa Leone | Heated Pool & Spa, Pet Friendly, Putting Green Why You'll Love This Home Tucked on the northern end of Sie ...
From $519 per night (USD)Expedia
From $146 per night (USD)VRBO
Quiet and Comfortable Condo Near Turtle Beach on Siesta Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida ...
From $146 per night (USD)VRBO
From $149 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 $149 per night (USD)VRBO
From $222 per night (USD)VRBO
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 $222 per night (USD)VRBO
From $266 per night (USD)Expedia
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 $266 per night (USD)Expedia
From $748 per night (USD)VRBO
⭐️ Elegant 2 BR + Den, Heated Pool, Steps to Siesta Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect getaway! This recently remodeled ground-floor apartment features a washer/dryer, dishwasher, mic ...
From $748 per night (USD)VRBO
From $157 per night (USD)Expedia
Newly renovated cozy and modern 2 bed. appartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy beautiful Sarasota while staying in our cozy, fully renovated 2 bedroom apartment in duplex home . Close to many a ...
From $157 per night (USD)Expedia
From $465 per night (USD)VRBO
Island House Beach Resort 18S
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This beautifully appointed 1-bedroom, 2-bathroom condo offers comfort, style, and spectacular Gulf views. The spacious p ...
From $465 per night (USD)VRBO
From $318 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 $318 per night (USD)Expedia
From $478 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 $478 per night (USD)VRBO
From $473 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 $473 per night (USD)Expedia
From $457 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 $457 per night (USD)VRBO
From $392 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 $392 per night (USD)Expedia
From $473 per night (USD)VRBO
Blue Seas & Sand 2BR Beach Club Siesta 200C 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 $473 per night (USD)VRBO
From $416 per night (USD)Expedia
Steps to Siesta Key beach, restaurants and shops!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
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 $416 per night (USD)Expedia
From $634 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 $634 per night (USD)VRBO
From $416 per night (USD)Expedia
On Siesta Key Beach - no streets to cross! Large, heated pool.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
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 $416 per night (USD)Expedia
From $540 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 $540 per night (USD)VRBO
From $175 per night (USD)Expedia
Cabana Royal with swimming pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautiful room has a private entrance with private bathroom and queen size bed. Brand new W/D included! Only five m ...
From $175 per night (USD)Expedia
From $468 per night (USD)VRBO
2BR Beach & Trolley–Beach Club Siesta 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 $468 per night (USD)VRBO
From $391 per night (USD)Expedia
First Lido - New pool deck, and landscaping, New elevator, Freshly painted
- 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 $391 per night (USD)Expedia
From $653 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 $653 per night (USD)VRBO
From $461 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 $461 per night (USD)Expedia
From $442 per night (USD)VRBO
Tropical Waters & Sunsets–Beach Club Siesta 106B 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 $442 per night (USD)VRBO
From $378 per night (USD)Expedia
Spacious Updated 7 Min to Beach. Loaded w/amenities Private and fenced yard PETS
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Spacious 1,700 Sq Ft Coastal Retreat 🦩 Experience total relaxation in this fully renovated home, perfectly designed fo ...
From $378 per night (USD)Expedia
From $932 per night (USD)VRBO
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 $932 per night (USD)VRBO
From $676 per night (USD)Expedia
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 $676 per night (USD)Expedia
From $597 per night (USD)VRBO
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 $597 per night (USD)VRBO
From $477 per night (USD)Expedia
Gulf Waters-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 $477 per night (USD)Expedia
From $179 per night (USD)VRBO
Sleeping Studio, Secure & Cute Downtown between Siesta & Lido Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a small room with cuteness and amenities, poster bed with space to store underneath, coffee maker/small refriger ...
From $179 per night (USD)VRBO
From $288 per night (USD)VRBO
A Prime Location..St Armand's circle, Lido Beach, Shopping, Dinning and Fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If walks down the white quartz sands of Lido Beach and strolling around St Armands Circle sound like time well spent, th ...
From $288 per night (USD)VRBO
From $340 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 $340 per night (USD)VRBO
From $324 per night (USD)VRBO
Sunny Cottage🌴half mile to Downtown-near famous beaches
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Relaxing and charming 3 bedrooms cottage half mile to Main steet, Downtown, parks, restaurants, art galleries,boutiques ...
From $324 per night (USD)VRBO
From $479 per night (USD)VRBO
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 $479 per night (USD)VRBO
From $3588 per night (USD)Expedia
Rare private beachfront estate on the Gulf.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Wake each morning to the soft rhythm of waves and step out onto a stretch of pristine, powdery sand your own private esc ...
From $3588 per night (USD)Expedia
From $249 per night (USD)VRBO
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 $249 per night (USD)VRBO
From $357 per night (USD)Expedia
Coastal Tropical Oasis With Salt Water Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Our home is the perfect spot for a getaway with friends, relaxing family vacation Our goal is for our guests to feel lik ...
From $357 per night (USD)Expedia
From $479 per night (USD)VRBO
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 $479 per night (USD)VRBO
From $717 per night (USD)Expedia
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 $717 per night (USD)Expedia
From $420 per night (USD)VRBO
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 $420 per night (USD)VRBO
From $313 per night (USD)Expedia
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 $313 per night (USD)Expedia
From $280 per night (USD)VRBO
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 $280 per night (USD)VRBO
From $169 per night (USD)Expedia
*** Downtown Bungalow ***Beaches / Restaurants / Cafes***Just Minutes away!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***VR24-00150***This charming cottage is the perfect place for your stay in downtown Sarasota. The space: This two b ...
From $169 per night (USD)Expedia
From $416 per night (USD)VRBO
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 $416 per night (USD)VRBO
From $3265 per night (USD)Expedia
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 $3265 per night (USD)Expedia
From $152 per night (USD)VRBO
Beach Vacation House - Minutes from the Beach and Hiking trails
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful renovated 2 bedroom 2 bath 1900 sq ft home is minutes from the beach and hiking trails. It has a huge out ...
From $152 per night (USD)VRBO
From $674 per night (USD)Expedia
❤️ Charming Coastal Pool Home - 1 Mile to Siesta Key - Relax & Unwind
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your Sarasota Sanctuary Awaits Welcome to your private coastal retreat. This beautifully refurbished 3-bedroom, 2-bath ...
From $674 per night (USD)Expedia
From $565 per night (USD)VRBO
❤️ Lovebirds' Retreat - Steps to Siesta Key Public Beach -
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from Siesta Key Beach, this 1BR/2BA townhouse is perfect for two. Enjoy 2 balconies with sunset views of the beac ...
From $565 per night (USD)VRBO
From $228 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 $228 per night (USD)Expedia
From $149 per night (USD)VRBO
Luxurious Living Steps to Lido Beach & Walking Distance to St. Armands Circle
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Freshly updated/painted condo with luxurious furnishings and steps to the Gulf of Mexico on exclusive Lido Key. This con ...
From $149 per night (USD)VRBO
From $135 per night (USD)Expedia
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 $135 per night (USD)Expedia
From $218 per night (USD)VRBO
Harbor Towers Yacht & Racquet Club Corner Suite: 4th Floor Bay & Pool Views & Great Workspaces
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Harbor Towers Yacht & Racquet Club 4th Fl Pool & Bay Views End Unit! Experience elevated island living i ...
From $218 per night (USD)VRBO
From $1473 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 $1473 per night (USD)Expedia