2 apartments to choose from: Key West Suite A relaxed beach experience. This cozy two bedrooms & den apartment, full 2 baths (1 King bed + 2 Twins + 1 Queen) 1,200 sq/ft. suite on second level with two private balconies and partial Gulf view from the den. This apartment is fully furnished and...

1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...

Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...

A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge. Perfect for travelers in search of uncomplicated seclusion. Residing in Siesta Keys most 'private' non-private beach neighborhood and just one marlin's length (5 steps) from yard to...

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...

Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two...

The Beach Place is a small group of tropical garden Floridian beach cottages located at Siesta Key Beach - 30 seconds to the sand and 10 - 15 minute walk to Siesta Village. We have a heated pool, tiki cabana wet bar for the guests to entertain at, beachfront picnic and BBQ, poolside BBQ, plenty...

Totally renovated adorable Siesta Key bungalow nestled on a shaded street just minutes from Siesta Key beach and the village of Siesta Key with a variety of shops, restaurants and nightlife. Drive into the circular driveway and park your car under the covered parking to be away from the 10 minute...

Imagine Yourself At (Tiny) Home: Beach life is best! Enter through the bright yellow, life-sized replica of a Siesta Key lifeguard stand, and drop your beach bags on the two stools beneath our surfboard-shaped breakfast bar. Passing through the living room, decorated with just a touch of...

Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests...

White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek. Highlights of White Sands Unit 303: Free high-speed WiFi Ground floor unit More than 200 channel cable TV DVR to watch your favorite show when you want to 50 inch...

This lovely 2BD/1BA apartment is located just 1 mile from beautiful Siesta Key Beach. Siesta Key was rated the #1 Beach in the United States by Dr. Beach (2011) and the #2 Beach in the U.S. in the 2013 TripAdvisor Travelers Choice Awards. Siesta Key was listed in 2014 by Smarter Travel.com as...

Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace or enjoy a dip in the large heated pool. Walk for miles on the beach...

Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the beach. The entire back of this house opens with...

PET Friendly! This one bedroom and one bathroom beach bungalow is located 150 yards away from the beach. You can walk to restaurants, shops and a great pool area. Queen bed and a sleeper sofa make it possible to sleep four. Enjoy your morning coffee on your private screened porch or while you walk...

It will be love at first sight with our tiny Blue Oasis; her cerulean color with bright white trim tells you you have arrived in the tropics, and her welcoming front porch is just big enough for you to engage in the southern pastime of porch sittin’. Cool off inside where the bleached white wood...

Casa Van Lopik (jardin), our garden facing suite, is a large 3BR home. Brought to you by Gertrude Rentals! Perfectly located between the best beaches, shopping dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always...

Please also visit siestakey-whitesands with the usual US ending. There you'll find lots of usedul information on the condo and a travel guide.White Sands Village is located on Siesta Key, just few steps from Siesta Beach and directly on the canal across from Philippee Creek.Highlights of White...

This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is...

A Gertrude Rentals property. Enviable location just steps away from everything! The Siesta Key Village Studio is an accommodating ground floor, one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one...

This Siesta Key 3 Bedroom 2 Bath Home has been completely remodeled. This home is 1 block from the Famous Siesta Key Beach. Granite counter tops, to accent the new white cabinetry. Beautifully tiled bathrooms with all new hardware. All walls beautifully textured. Screened Lanai. Nice back yard. 1...

YOUR PRIVATE GETAWAY ON THE KEY ASK ABOUT OUR SUMMER SPECIALS!!!!!!!!! Does not include Weekends or Holidays!!! Looking to relax, Flip Flop Cottages is the place to be for a quaint and private vacation in Siesta Key, Florida. Come and stay at our serene environment and enjoy and visit all the...

Located near the South Village of Siesta Key. This newly updated 2 bedroom duplex has it all. A new dipping pool to cool off the hot summer days, along with a BBQ and fire pit for the winter. Lots of space, all new furnishings throughout the home, the large eat in kitchen has plenty of room for...

A Gertrude Rentals property! Large 3BR home perfectly located between the best beaches, shopping dining and entertainment on Siesta. Leave the car behind. After the beach, you could wander to town for fresh oysters and seafood, drinks, live music or ice cream, or just relax in a tropical garden...

Welcome to Casa Tegula! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous...

Brand new tiny home near the beach! Why stay in a hotel room or even a boring old house when you can stay in a brand new tiny home. Come check out the only tiny beach hotel in America. We are located less than a mile from the world famous Siesta key Beach rated the number one beach in America by...

Welcome to Casa Junonia! Our newly constructed luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor,...

A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room has...

ENJOY CASUAL SIESTA KEY LIVING IN THIS LOVELY HOME WITH SEPARATE DETACHED GUEST LIVING SPACE!! The separate guest quarters allow entertaining while providing your family or guests their own private retreat. It is all about the lifestyle! In total this home hosts 4 bedrooms and 3 baths on the island...

A Gertrude Rentals property! Our Top Location! Leave the car behind. Richly furnished, perfectly nestled between the best beaches, shopping and dining on the Island, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. Our living room, master bedroom and...

A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of the SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your...

Welcome to Casita Morning Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent bathrooms, new appliances, new washers/dryers,...

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

Welcome to Casa Stolida! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing...

3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach....

Villa Cascada is a uniquely configured private home featuring a heated pool/waterfall, 4 bedrooms, 4 bathrooms that sleeps 12, with 2 living areas and 2 kitchens and an almost unbelievable pool courtyard surrounded by lush gardens and a tall privacy wall enclosing the entire property. Each of the...

Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy...

The Sea Wave and Sea Shell are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. Please Note: These units [Sea Wave & Sea Shell] can be rented separately. Combined, these units are called: Villa Brisa Marina...

Welcome to Casa Coquina! Our newest luxury cottage has all the amenities your large group [up to 12!!!] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout the entire three-story building, an elevator to access each landing from the ground floor, gorgeous and...

Brand New , Gated Residence steps from Siesta Key Beach . Perfect location between the village and crystal sands of Siesta Beach!! Bar's, Restaurants, Shopping, Sport Rentals……..EVERYTHING is within walking distance…..NO CAR NEEDED!!! This brand new 2700 sq ft private residence is simply...

Welcome to The Pearl by the Sea. An absolute one of kind, limited edition home located on prestigous Siesta Key featuring a private heated pool and spa, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. You have arrived... If you have ever gone searching for...

Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy...

It is a 220-square-foot luxury tiny home, and it offers all of the facilities and conveniences you need for living comfortably The Dragonfly tiny home features a standard-sized bed in the spacious, loft bedroom, as well as a convertible Ikea bed that turns into a couch in the living quarters....

PURA VIDA OASIS: This spectacular bright cheerful, canal front cottage with a heated pool & spa has 5 bedrooms and 3 baths and it can sleep a total of 13. As you enter Pura Vida Oasis, you will notice an eclectic wine storage rack and desk area awaiting on your right and a lovely dining area with...

Welcome to the Honey Mango Cabana! This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. This property is very unique as it is one half of 'Mango Manor,' which is comprised of the two separate cabanas, Honey and Juicy Mango. This provides a fantastic and unique...

The Coral Reef and Star Fish Casitas are two separate units which can be uniquely configured to create Villa Dom Bisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross]. Please Note: These units [Coral...

Welcome to The Canopy Cottage! Nestled deep into a beautifully canopied tree neighborhood, this lovely 4 bedroom, 3 bathroom home features a heated pool and spa under a screened in lanai just a few minutes from Siesta Key's #1 Beach! Take a moment to breathe in the peace and serenity under the...