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Siesta Key Vacation Rentals, Homes and Condos for Rent near the Beach

Book Your Siesta Key Florida Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your stay enjoyable.

We have partnered with a major provider for Vacation Rentals by Owner directly through Sarasota Vacation Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places To Rent in Siesta Key Florida.

Siesta Key Gulf Front Condo

Siesta Key Condo Star 5.0 Star Review

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor and is .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Casa Blanca B08 Villa

Siesta Key Villa Star 5.0 Star Review

2 Bedroom/ 2 Bath Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.

Master Bedroom new, King size pillow-top mattress, a tropical ceiling fan, upscale furnishings and is tastefully decorated for ultimate relaxation and comfort.

Second Bedroom is tastefully furnished with 2 twin beds.

Our v.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


CA202S - Siesta Key Luxurious Beachfront Condo

Siesta Key Condo Star 3.0 Star Review

Our second floor, gulf-front apartment offers a spectacular, uninterrupted view down beautiful Crescent Beach. Located on the southwest corner of the south building, its screened lanai provides a sunny front-row seat for beach and sunset watching with shelter from the occasional north breeze.

Crescent Beach, with its three miles of white, su.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


CA403N - 2/2 DIRECTLY ON THE BEACH - 4th Floor Views - Vacation Getaway

Siesta Key Condo Star 4.6 Star Review

403 N.
Last minute specials!
$200 off during the weeks of August 20/2022 to September 3/2022 and September 24 to October 1, 2022.

Come and enjoy the sun and moon light on the Gulf and feel the powder white sands of Siesta Key between your toes, where the sand never gets hot, steps away from your condo.
We are located on the 4th-f.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Sprinkle of Irish charm, beautifully updated, Siesta Dunes 8-205

Siesta Key Condo Star 4.3 Star Review

Welcome to our condo 8/205. Featuring beautiful wood floors, Siesta Dunes Beach 205 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, it’s easy on the wallet while its lovely atmosphere makes it a great home to return to for relaxing.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Old World Florida at its Best

Siesta Key Cottage Star 5.0 Star Review

Extremely comfortable 2 bedroom, 2 bath cottage on the grand canal. Enjoy your morning coffee on the dock, breakfast in the screened lanai or afternoon relaxation poolside. There is a peaceful park in front and it\'s a great neighborhood for long evening strolls. The number one beach in the USA is only a four minute walk, and the nightlife and res.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 2


Vacation Home


Rarely available dockside retreat! With pool and clubhouse!

Siesta Key Condo

BOATING & BEACHGOER PARADISE! This three bedroom, three full bath townhome includes an attached one car garage. Tranquil harbor views with sunset and fishing out your back door. This Luxuriously landscaped gated community offers a pool, spa, tennis & pickle ball court and clubhouse. All just a short stroll to the POWDER WHITE SANDS OF SIESTA KEY BE.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Clean and Perfectly Remodeled Townhome, Steps From the Private Beach

Siesta Key Private vacation home Star 4.8 Star Review

Impeccably Clean, the reviews speak for themselves!

Located at Siesta Beach House, 5950 Midnight Pass Road, this luxurious Beach Townhouse, is just steps to its private beach entrance. Totally renovated top to bottom. This 2 bedroom, 2.5 bath Townhome is amazing and the best unit in the complex. Well, 302 is a close tie but that\'s mine .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 5


Vacation Home


Aloha Kai - Unit 3-close to the pool!

Siesta Key Apartment

Fully furnished villa offering living room, dining area, fully equipped kitchen, two bedrooms and one bathroom. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offers a private parking space directly outside your front door........read more

2 Bedroom(s)
1 Bath(s) Sleeps 5


Vacation Home


New Listing! Ground floor, easy access to the pool and beach! Siesta Dunes 2-104

Siesta Key Condo Star 4.0 Star Review

This ground floor 2 bedroom, 2 bathroom unit is nicely updated and comfortably furnished with easy access to the pool and the beach. Our Property is managed by the Siesta Dunes Rental Office and the staff is available to assist you during your stay.

Amenities include:

Gulf View, from 1st Floor

King in Master Bedroom

Show.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Harbor Towers Yacht & Racquet Club -Siesta Key Beach Condo

Siesta Key Condo Star 4.8 Star Review

Siesta Key Beach Condo “USA #1 Rated Beach”
This newly renovated and up-to-date condo is across the street from the beach and has open views of the inter-coastal waterway with boats and dolphins coming and going throughout the day.
The condo is a fully furnished 2 bedrooms/2-bath unit with three flat screen TV’s, FREE WIFI and a DVD Pla.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5


Vacation Home


Luxury Waterfront Views / Pool / 1400sf / 2 min to Beach

Siesta Key Condo Star 4.5 Star Review

Our home, located on Siesta Key, with breathtaking intercostal water views is fully furnished with all the amenities you would expect just as in your home. After spending a day relaxing at the world famous Siesta Key Beach with quartz-crystal sand as white and soft as powdered sugar, come back home and enjoy the evening relaxing on one of our 3 la.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


New Listing - Bali Hai House - A Siesta Key Water Front Cottage

Siesta Key Private vacation home Star 5.0 Star Review

Everything you\'re looking for in a comfortable and convenient vacation is waiting for you at Bali Hai House! This gorgeous waterfront home is fully equipped with a spacious outdoor patio, fire pit, and private screened in heated pool. Hang out on the hammock and watch boats drift by or take a short walk to Siesta Key Beach. This spot is ideal for.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Beautiful, Modern Coastal Condo, 2-205

Siesta Key Condo

Beautiful updated, modern 2 bedroom, 2 bathroom coastal condo overlooking the pool and Gulf of Mexico.
This unit features updates throughout:
The kitchen features unique leathered marble counter tops, stainless steel appliances and custom cabinets.
The bedrooms and bathrooms feature modern furniture and luxurious updates. The master bedro.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


1010-1012 Point of Rocks- Brand new remodel and by the beach!

Siesta Key Private vacation home Star 4.8 Star Review

Beautiful Duplex located 1 house away from beach! Amazing Location! These beautifully decorated duplexes feature all the conveniences of home with a fully equipped kitchen and linens provided. The duplexes sleep 16 and are equipped with a king in the master bedroom, a queen and 2 twins in the guest bedrooms and in 1010 the master features a quee.......read more

6 Bedroom(s)
6 Bath(s) Sleeps 14


Vacation Home


Crescent Street 1138 B, Walk to the beach, Pool, 1 Bedroom, Pet Friendly

Siesta Key Private vacation home Star 4.2 Star Review

Half-hidden by lush tropical foliage, Crescent Street 1138 B is paradise for anyone who longs to relax in time-honored Florida style. Just a few blocks from Siesta Key’s quartz-white beach and the renowned Point of Rocks, the pet-friendly home is a haven in and of itself.

The first thing you’ll notice as you drive up is the house’s h.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Tivoli by the Sea-Unit 504 - Gorgeous unit with a gorgeous view

Siesta Key Apartment Star 5.0 Star Review

Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!!! This unit sleeps 5 with a king in the master, a full and twin.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5


Vacation Home


101-Excelsior- Updated and Full Gulf Front!- 2 week minimum

Siesta Key Condo Star 4.8 Star Review

PERFECT PLACE TO WATCH THE SUNSET!! 2 bedroom/2 bath gulf front condo located on Crescent Beach. Walk out onto your patio and directly down to the courtyard area with a private back entrance for easy access to the pool area and beach access. . This unit features a King bed in the master and 2 Queen beds in the guest room. It\'s only a short walk .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Tivoli by the Sea-Unit 407 - Gorgeous View of the Gulf

Siesta Key Condo Star 4.6 Star Review

Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!! This unit sleeps 5 with a king in the master, and a queen & twi.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Buttonwood 472 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Siesta Key Condo Star 5.0 Star Review

Fabulously decorated 3/2 corner unit on the seventh floor. Wood flooring and ceramic tile throughout. The updated kitchen and baths adorn granite counter tops. Decorated with soft leather sofa and chairs, the living room comes with TV/VCR/DVD. Step out onto the screened lanai and feel the subtle tropical breeze. Experience the view of Crescent Beac.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Siesta Key Condo

Siesta Key Condo Star 5.0 Star Review

Spacious condo, nicely furnished and private ground floor unit. 1 br, 1 ba in tropical setting, fishing pier and private beach access with great sunsets, pool, clubhouse facing the Gulf, walking distance to village, shops, restaurants and Siesta Key public beach. .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Our House at the Beach C-220 Perfect Getaway!

Siesta Key Condo Star 4.0 Star Review

This completely renovated and luxurious Lake House townhome directly adjacent to America\'s famed #1 beach - Siesta Beach, offers a spacious bi-level layout that includes separate dining and living rooms with Brazilian cherry hardwood floors. The eat-in kitchen is fully stocked with pots, pans, dishes, and flatware and a suite of stainless steel ap.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Historic & Lovely ❤ Walk to the Beach or Village

Siesta Key Private vacation home Star 4.5 Star Review

How far from the Beach? 150 steps or barely a 2 minute walk and you\'re on the Beach! Short walk to Siesta Village. Welcome to Prime-Time on Siesta Key - Wonderful, Clean & Cozy 2 bedroom, 2 full bathroom, Two-Story Villa that comfortably sleeps 4 adults. Enjoy 1000 sf of living space with huge upstairs living room, comfy couches, TVs in all rooms .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Siesta Key # Beach Oasis with special summer rates!!!

Siesta Key Condo Star 4.9 Star Review

Now with private Wifi. This One Bedroom, One Bath condo is just steps to the white, powdered-sugar sand of Siesta Key. Here at La Siesta Condominiums you also have easy access to Siesta Village and it\'s numerous restaurants, specialty shops, night life and other attractions.
Unit 217 is decorated in a modern tropical theme and overlooks our poo.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Top Location on Siesta Key! Private Gate into Village! No car required!

Siesta Key Private vacation home Star 5.0 Star Review

A Gertrude Rentals offering.  Two properties in the Siesta Key Village just a short walk to Siesta’s best beaches and sure to provide a combination of fun and rejuvenation you won\'t find in other getaways!   This package can accommodate up to 12 people and includes a 3BR unit and an additional studio apartment two for down each located near t.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 12


Vacation Home


Our House at the Beach E-404 Sugar Sands Beach View!!

Siesta Key Condo Star 4.3 Star Review

Just across the street from the acclaimed #1 Beach in the US. This beautiful two bedroom/ 2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities includ.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


1st Floor Gulf View, Convenient Walk Out to Pool w/ 3 Porches!

Siesta Key Condo Star 5.0 Star Review

Enjoy your beachfront vacation condo here in Siesta Key, with perfect sandy beaches right out your door. Siesta Key is a barrier island along the southwestern coast of Florida and is considered by beach experts to be one of the most beautiful beaches in Florida. When you stay with us at Siesta Dunes Condominiums, you stay in style and comfort, just.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5


Vacation Home


Very Clean and fun ! Sarasota Siesta key beach Condo 1/1 2 +beds

Siesta Key Condo Star 4.3 Star Review

Beautiful, secure, upgraded unit with new curve TV, Live in Amazing Siesta Key, modern upgraded condo. Enjoy one of the nicest beaches in the world in style, our condo is located on beautiful Siesta Key, completely furnished, accommodations include an additional pull down murphy bed. This third floor unit is completely furnished with all you need t.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Palm Bay Club Unit 311 with pools & hot tub - walk 1,500 feet to beach

Siesta Key Condo Star 4.5 Star Review

The Palm Bay Club Unit 311

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Walking distance to iconic Siesta Key Beach and steps from the pool and private Crescent Beach, this open-concept Palm Bay Club 2BR/2BA condo on the Gulf features plush f.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


5 Star LUXURY RETREAT on BEACH ROAD, SIESTA KEY BEACH, New POOL

Siesta Key Private vacation home Star 4.9 Star Review

One of the nicest private homes on Siesta Key Beach. We have the highest 5 star rating on Siesta Key. See Vrbo 802548 for more reviews of this home - . Stunning and spacious on Beach Road right across the street from Beach Access 10 (ranked number one Beach in US.) Please note that our vacation home consists of two units. This listing\'s pri.......read more

3 Bedroom(s)
5 Bath(s) Sleeps 8


Vacation Home


Tivoli by the Sea-Unit 404 - Beautiful View of the Gulf

Siesta Key Apartment Star 5.0 Star Review

Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!! This unit sleeps 4 with a king in the master, and two twin size.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


2700 sq ft home/guest home w/ private pool 200 steps to Crescent Beach - dogs OK

Siesta Key Private vacation home

Siesta Key Reverie

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Happiness is a private pool just 200 steps from the white, powdery sands of the number one rated beach in America, Crescent Beach! This single-story slice of paradise has a heate.......read more

4 Bedroom(s)
5 Bath(s) Sleeps 8


Vacation Home


Stunning Sunset Views from this well appointed one bedroom Condo.

Siesta Key Apartment Star 4.8 Star Review

Enjoy watching the beautiful sunsets every night from your own private lanai/patio in this one bedroom, one bathroom condo. Located at Siesta Beach with Siesta Key\'s famed "Village" a short walk away. This condo has everything you are looking for. Amenities include: beach access, BBQ, picnic tables (at the beach), Gulf view, western sunsets, famil.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


New Listing! The Coral Reef | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home

Welcome to The Coral Reef! This group of 3 private units is perfect for families and groups, with the ability to accommodate up to 12 guests, with 3 bedrooms and 3 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-ren.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 12


Vacation Home


Chinaberry 423 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Siesta Key Condo Star 4.0 Star Review

Brand New to the Rental Program! Absolutely GORGEOUS 2 bedroom 2 full bath unit on the 2nd floor in the main tower on the Gulf Side. Overlooking the beautiful tropical grounds, pool and the famous, white sugary sands of Crescent Beach! Tastefully decorated in a very light and bright, modern beach-theme, leather furniture in the living room, very up.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Key Apartment Star 4.7 Star Review

Light, bright and cozy in the HEART of Siesta Key Village! Open floor plan including queen-sized murphy bed, Smart TVs, & Strong WIFI. Amazing balcony for the best people watching on Ocean Blvd. Quick & easy three minute walk will put you on the #1 Beach in the USA, Siesta Beach! This beautifully appointed apt. is perfect for those who will not min.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 3


Vacation Home


Paradise! Remodeled 2 bedroom 2 bathroom with incredible views

Siesta Key Condo Star 4.9 Star Review

This spacious large ground floor corner unit is just steps away from the pool, hot-tub, fishing pier and poolside BBQ\'s. One of the few units with an incredible direct view of the bay and pool. Voted the #1 beach in the USA, Crescent Beach, with it\'s beautiful quartz sand which looks and feels like powdered sugar, is just a short walk through t.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Siesta Dunes Beach 201, Completely Renovated, 2 Bedrooms, Sleeps 6, Spa, Large H

Siesta Key Condo Star 4.3 Star Review

This unit has been newly renovated. Stunning seaside decor, new kitchen, baths, paint, and luxury vinyl plank flooring throughout. Decked in pure tropical style, Siesta Dunes Beach 201 in Siesta Key, Florida is an ideal choice for families planning to spend all their daytime hours at the pool or the gorgeous on-site beach. As a gulf-side property, .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Buttonwood 940 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Siesta Key Condo

Beautifully and recently updated 3BR/2BA private, end/corner unit with ceramic tile floors in all living areas. Completely renovated bathrooms, tile showers with rain shower heads in both bathrooms, newly tiled and painted master bedroom and second bedroom. All new fans with lights in condo. New glass lanai doors and all new windows. Spacious with .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Charming home on quiet street one block from Siesta Beach.

Siesta Key Private vacation home Star 5.0 Star Review

Comfortable private home on a quiet street one block from Siesta Beach. Lush tropical fully fenced in backyard has a gas grill and comfortable chairs and table, under a shade sail with cafe lights. Walk to the beach or Siesta Village. Fully furnished kitchen has everything you need to feel at home. Enjoy comfortable couches and beds, fast internet.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Slice of Beach Paradise | Private Wraparound Balcony with Amazing Gulf Views

Siesta Key Private vacation home Star 4.0 Star Review

Beach Road Condo Unit 2

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click \'Book Now!\'

Perched by the shoreline, this 3BR/2BA townhome is a slice of beach paradise. With the Gulf just a 2-minute walk away, enjoy the stretches of sugar-white sand and turquoise .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Spectacular Waterfront - Panoramic Views of Intercostal 3Bed- 2 Bath

Siesta Key Condo Star 5.0 Star Review

This spacious first floor waterfront condo has over 1879 sq. of indoor/outdoor living space. Boasting two gigantic elevated private outdoor patio’s with new outdoor furniture, along with water views of the Intercostal, direct access to marina, designated parking and your own private entrance. Siesta Beach #5 in the World #1 in the USA 2017!! P.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


2 units next to each other on the #1 Beach in USA. Perfect vacation in Paradise

Siesta Key Condo

Siesta Key gulf side rental on one of the widest and most beautiful stretches of beach in the world. See why siesta key\'s beach has been rated #1 in the USA! There is a one month minimum rental for this property. You could be one of the first to stay here after a gut renovation down to the studs. This 1800 square foot, 2 bedroom 3.5 bath condo has.......read more

3 Bedroom(s)
5 Bath(s) Sleeps 10


Vacation Home


New Listing! Sea Foam | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home Star 5.0 Star Review

Welcome to Sea Foam! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the pe.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Midnight Cove #714, Bayside in Siesta Key, FL

Siesta Key Condo Star 4.5 Star Review

Thank you for your interest in Midnight Cove #714, a 2BR-1 1/2BA, 860 sq. Ft., 1st floor, bayside beach vacation condominium, with screened lanai view of the boat docks, and lagoon, located in Siesta Key, FL, with the central location of the Midnight Cove gulfside and bayside properties offering many area conveniences within a few minutes walking d.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Newly Renovated Family Fun 2BR w/ Pool - Walk to Beach

Siesta Key Private vacation home Star 4.6 Star Review

Newly renovated gated beach access apartment with a pool. This is a two bedroom and two bath apartment that makes up one unit in a quadplex. It is on a very quiet private road that leads to a gated beach access way that only residents on this street have access too.

The house was completely redone and has all new furniture, sheets, pillows,.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Bay Isle Bliss | LIMITED OFFER: Book 4 nights get 3 nights free!

Siesta Key Private vacation home Star 4.8 Star Review

LIMITED OFFER: Book 4 nights get 3 nights free! Valid for vacation dates now through 12/15/22. Contact us for more details!

Bay Isle Bliss is a newly updated, single-family home residing on Siesta Key\'s north end. Three bedrooms and two bathrooms can accommodate up to 8 guests alongside luxury amenities including a private, heated pool and.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Key West style beach cottage JUST STEPS from #1 SIESTA KEY BEACH!

Siesta Key Cottage Star 4.9 Star Review

**PLEASE do NOT request to book before contacting hosts. USE "Contact Host button" (blue letters under owners photo on right) BEFORE requesting to book so we can assure this special spot is a good fit for you.**
NO dogs over 20 pounds and ONE dog only. NO more than 2 guests with ONE car.
LOCATION!! Just steps to beach access #7 and a block f.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2


Vacation Home


Top in Siesta Village at Best Beaches, Food & Entertainment! Casa Van Lopik.

Siesta Key Private vacation home Star 4.9 Star Review

A Gertrude Rentals property.  In the Siesta Village just a short walk to Siesta’s best beaches and sure to provide a combination of fun and rejuvenation you won\'t find in other getaways!  Casa Van Lopik is 100% private with two large 3BR units capable of accommodating up to 20, and a lush tropical indoor/outdoor patio lounging and dining area........read more

6 Bedroom(s)
4 Bath(s) Sleeps 22


Vacation Home


Prem 2Bed/2Bath Gate House Cottage with private beach access!

Siesta Key Cottage Star 4.8 Star Review

Wonderful stand alone cottage ready for your perfect retreat! Master bedroom has a king size bed, full private bathroom, walk in closet, flat screen TV and attached access to the secluded rear yard. Second bedroom has two twin beds with large closet. The large open floor plan has a living room with a couch, love seat and flat screen TV. The un.......read more

2 Bedroom(s)
2 Bath(s)


Vacation Home


Best Location Siesta Key Village Beach, Restaurants, Bars10% Friends Discount

Siesta Key Apartment Star 4.5 Star Review

Apartment /entire First floor

This charming Siesta Key vacation rental home is a unique combination of relaxation and fun, a beautiful kitchen, dining area, living room and outdoor patio area. This beautiful property has access to a heated pool (the pool is shared between the two units in the house). This home has every amenity you could fat.......read more

3 Bedroom(s)
3 Bath(s)


Vacation Home


Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

Siesta Key Cottage Star 4.7 Star Review

Location, location, location. Our charming 3-bedroom 2 bath Florida beach cottage, which is over 1000 feet and sleeps 6, which we call the “Manatee Cottage” is across the street from the soft, white sands of the world-famous Siesta Beach which is consistently rated the best beach in the United States (you will be a 5 minute walk from access 7)........read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Luxurious Waterfront Retreat with bay & city views minutes from Beach

Siesta Key Private vacation home Star 5.0 Star Review

Villa Siesta sits poetically in a walled, gated garden on deep, azure-colored Hansen Bayou with views of Sarasota Bay & City skyline. This architecturally unique 5400 sf villa is built around a spacious tower with winding 3 story staircase opening to each living level.

The romantic residence is located just a few blocks from Shell Beach, les.......read more

4 Bedroom(s)
6 Bath(s) Sleeps 8


Vacation Home


Bright and Airy 4th floor condo at Fisherman's Haven with Private Beach and Stunning Water Views! FH

Siesta Key Condo Star 5.0 Star Review

Bright and Airy 4th floor condo at Fisherman\'s Haven with private beach and stunning water views!

Spacious, open-concept 2 bedroom featuring a roomy kitchen with breakfast bar, large bedrooms, and nicely furnished oversized living room with Bay views. King beds and large closets are provided in both bedrooms, and both have gorgeous views o.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

siesta key Condo Star 4.9 Star Review

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL

Top beachfront unit at Fisherman\'s Cove!! Fisherman\'s Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of t.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Tivoli by the Sea-Unit 505 - Gorgeous view with sleep sofa

Siesta Key Apartment Star 4.7 Star Review

Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!!! This unit sleeps 5 with a king in the master, a full and twin.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 5


Vacation Home


New Listing! Sea Escape | Located in Siesta Key Village, Walk to the Beach!

Siesta Key Private vacation home

Welcome to Sea Escape! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.

Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Aloha Kai - Unit 1 close to pool!

Siesta Key Cottage Star 4.2 Star Review

Updated recently in the kitchen with a quartz counter top and all new appliances! Also, many new furniture pieces including a beautiful dinning table set (seats 8), a king "Tommy Bahama Paradise Point Plush" mattress set in the master bedroom, and a queen "Perfect Sleeper Plush" mattress set in the second bedroom. Also a queen sleeper couch was r.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Steps to the ⭐ Beach, Short Walk to the Village

Siesta Key Private vacation home Star 4.9 Star Review

How far from the Beach? 150 steps or barely a 2 minute walk and you\'re on the Beach! Short walk to Siesta Village loaded with restaurants, bars, shopping, clubs and more!
Welcome to Convenience on Siesta Key - Wonderful, Clean & Cozy 2 bedroom, 2 full bathroom, single-level Villa that comfortably sleeps 4 adults. Enjoy 1000 sf of living s.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Updated! Walk to SK Beach, 2 Heated Pools, WiFi/Cable, Screened Lanai, Tennis/Pickleball, Gym

Siesta Key Condo Star 5.0 Star Review

New Flooring 12/21...Smashing second story, 3 bedroom town home in popular Siesta Bayside on the Bay and for the best part.....you can walk to Siesta Key Beach...via our private access!! Resort style amenities include TWO heated swimming pools, Clubhouse & Fitness Center, BBQ Grill area with tables, 2 Tennis/Pickle-ball Courts with lights for ni.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


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