Waterfront holiday rentals in Gulf Gate Estates

A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.

4.9 out of 5 average rating, 134 reviews

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.

4.94 out of 5 average rating, 126 reviews

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

4.98 out of 5 average rating, 222 reviews

Condo in Longboat Key

Oceanfront LBK: Relax & Recharge!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

4.95 out of 5 average rating, 396 reviews

Tiny home in Sarasota

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.

4.97 out of 5 average rating, 357 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. If we are booked check out our additional units under our profile.

4.9 out of 5 average rating, 205 reviews

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

4.86 out of 5 average rating, 176 reviews

A cozy porch area features a hanging swing adorned with colorful cushions, complemented by a small dining table and chairs. The entrance is framed by green lattice work, creating a welcoming space. A sign with the text 'WELCOME' is mounted on the wall.

Cottage in Siesta Key

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, Keurig in the kitchen, stocked with everything but your clothes and toothbrush.

A well-appointed kitchen features light-colored cabinetry and countertops, with modern appliances including a microwave and oven. An island provides additional workspace, while a dining area is visible in the background. Soft lighting creates a welcoming ambiance throughout the space.

4.97 out of 5 average rating, 116 reviews

Palm Bay Club! Resort Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

4.91 out of 5 average rating, 360 reviews

Guest suite in Sarasota

Siesta Keys stylish and affordable Airbnb.

Relax while you stay in a colorful and warm Siesta Key/Sarasota neighborhood home that is only minutes from the famous Siesta Key beach. Enjoy your private, safe, and comfortable suite while being in close reach to all that Florida has to offer. Your suite is spacious and accommodating, wether your an individual, couple, family, or group of friends we have the space and amenities for you to maximize both your comfort and fun time while here in Florida :-)

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

4.92 out of 5 average rating, 148 reviews

Sea Shell Ocean View On Beach Walk Everywhere Pool

Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 325+ reviews that ave FIVE STAR!

4.94 out of 5 average rating, 106 reviews

A screened lanai encloses a private saltwater pool, featuring a shallow entry and a vibrant pink float. Two lounge chairs are positioned nearby, surrounded by greenery that enhances the serene pool area.

Home in Sarasota

Minutes to Siesta Key, heated pool & tiki on water

Coral Harbor is conveniently located in Gulf Gate Estates, just 3 miles to the beach. The 1 acre property sleeps up to 12, with a private heated salt water pool, mature trees, lanai, sun deck, and bonus "Tiki" bar. You'll love the deck overlooking the lake to feed the turtles! The home has all the modern amenities you would expect from a vacation home. Minutes to Siesta Key, easy access to Venice Beach, Lido Beach, downtown Sarasota, AMI & more!

A detailed map highlights the location of Siesta Key, showcasing nearby points of interest and roadways. The Gulf of Mexico is indicated to the southwest, while the surrounding areas and other keys are marked, providing context for travel and exploration.

4.87 out of 5 average rating, 106 reviews

Bayside Sunrise Cottage on Siesta Key!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, stocked with everything but your clothes and toothbrush.

Popular amenities for Gulf Gate Estates waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

5 out of 5 average rating, 23 reviews

Beachfront Corner Condo | Sunset Gulf Views

4.87 out of 5 average rating, 134 reviews

Low Tide @ Tides Inn

4.91 out of 5 average rating, 137 reviews

Newly Remodeled Beachfront Studio - On the sand!

4.85 out of 5 average rating, 34 reviews

The living area features a white sofa paired with two pink accent chairs, creating a refreshing ambiance. A wooden coffee table sits on a light-colored rug, while plants and beach-themed artwork add charm. Large sliding doors provide natural light and connect to the outdoor space.

Apartment in Siesta Key

Condo Kokomo - stay ON the beach in Siesta Key!

4.98 out of 5 average rating, 127 reviews

A spacious living room features a large grey sectional sofa with teal accent pillows, a wooden coffee table, and a light blue area rug. Large glass doors provide access to an outdoor area, while a vibrant seascape painting adorns the wall.

Apartment in Bradenton

Sweet Retreat at Shorewalk!

A dining table showcases a glass top with intricately woven placemats. Each setting features decorative plates and neatly folded napkins secured with decorative rings. Sheer curtains frame the window, offering glimpses of lush palm trees outside.

4.88 out of 5 average rating, 228 reviews

Las Palmas Beach Rentals Unit 1

Apartment in Longboat Key

Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.

4.96 out of 5 average rating, 114 reviews

Longboat Key-OCEAN FRONT- on the beach

5 out of 5 average rating, 14 reviews

The exterior of the condo is shown, featuring a spacious deck surrounded by palm trees, with an umbrella providing shade. Large windows offer a view into the interior space, and ample outdoor seating is visible. A concrete path leads through the outdoor area.

Apartment in Sarasota

Cozy Condo in Siesta key with boat dock

Waterfront house rentals

4.78 out of 5 average rating, 538 reviews

An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.

Home in Siesta Key

Beachfront Getaway in Siesta Key

5 out of 5 average rating, 154 reviews

Home in Siesta Key

Beach, Village, Dock & Private Pool! One-of-a-kind

4.98 out of 5 average rating, 123 reviews

A spacious rooftop terrace overlooks a marina filled with boats. Lounge chairs are arranged for relaxation, surrounded by greenery. Outdoor tables are set for dining, with views of water and distant shorelines under a partly cloudy sky.

Home in Bradenton

Bradenton Gem | IMG & AMI | King Ste + Beach Gear

4.99 out of 5 average rating, 124 reviews

A bright kitchen is showcased, featuring modern cabinetry and appliances. A small dining area with two wooden stools is positioned next to a white countertop. Natural light fills the space through a nearby door and window, creating an open atmosphere.

Home in Cove

Tranquility on the bay.

4.94 out of 5 average rating, 149 reviews

A screened-in pool area is showcased, featuring a heated pool with clear blue water. Sunlight casts shadows on the tiled surface, while a picturesque view of a private lake and surrounding greenery is visible in the background.

Home in Sarasota

Lake Front House with a Pool

4.9 out of 5 average rating, 152 reviews

A serene beach scene is captured with gentle waves lapping against the shore. The clear water displays various shades of blue and green, while a sandy coastline extends into the distance. People can be seen enjoying the beach, with a bright blue sky overhead.

Home in Siesta Key

Sea Club II Garden House

4.89 out of 5 average rating, 106 reviews

A serene outdoor seating area features several lounge chairs with cushions, positioned on a brick patio overlooking tranquil water. The setting is complemented by a soft sunset in the background, with lush greenery visible across the bay.

Home in Sarasota

Oceanfront home w/sunset views of Sarasota Bay

Superhost

A serene view of a lush property borders a small lake, framed by tall grasses and leafy trees. One can observe a snowy egret standing gracefully by the water's edge, surrounded by greenery and the subtle reflections of the landscape in the lake.

Home in Nokomis

4.82 out of 5 average rating, 101 reviews

The Lake View

Waterfront condo accommodation

A modern kitchen features white cabinetry and a spacious counter. Stainless steel appliances, including an oven and microwave, are visible. A decorative beach sign adorns the wall, and a bowl of fresh fruit sits on the counter, adding a pop of color to the bright space.

4.86 out of 5 average rating, 188 reviews

Best Siesta Key Condo - Rarely available

4.95 out of 5 average rating, 161 reviews

A cozy bedroom features a large green bed with multiple white pillows, complemented by two bedside lamps. The ceiling showcases a tropical leaf pattern, and mirrors adorn the walls. Natural light enters through a window, with white curtains framing the view.

Condo in Bradenton

KING bed + Anna Maria Island Beaches + Beach Gear!

A tranquil pool area is surrounded by palm trees, reflecting the clear blue sky. Lounge chairs are positioned around the pool's edge, inviting relaxation. The sun casts a warm glow over the scene, enhancing the peaceful ambiance of the resort.

4.98 out of 5 average rating, 125 reviews

Siesta Key For Me @ The Palm Bay Club

A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.

4.82 out of 5 average rating, 137 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

4.97 out of 5 average rating, 126 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Condo in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

4.99 out of 5 average rating, 162 reviews

A spacious living area features a blue sofa and striped armchair, complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, showcasing views of the turquoise Gulf. Light-colored cabinetry and decorative shelving enhance the inviting atmosphere.

Condo in Bradenton Beach

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

4.82 out of 5 average rating, 22 reviews

Condo in Sarasota

100 ft to Beach – 1BR Siesta Key Escape

A heated pool is surrounded by lounge chairs set on a white deck, with palm trees and lush greenery nearby. A multi-story building looms in the background, along with a tennis court visible at the side. A safety sign is placed by the gated entry.