Vacation rentals with outdoor seating in Longboat Key

4.98 out of 5 average rating, 104 reviews

A bright and airy living area features large windows allowing natural light to fill the space. Comfortable seating is arranged around a woven coffee table, with art pieces adorning the walls. A door leads to outdoor views, enhancing the inviting atmosphere.

Home in Terra Ceia

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

A glass sliding door opens to a private balcony, offering views of palm trees and the beach. Outdoor seating is visible, with a chaise lounge beside a small table. The serene ocean can be seen in the background, enhancing the coastal ambiance.

4.88 out of 5 average rating, 105 reviews

Beautiful Panoramic Gulf and Sunset Views.

Beachfront Bliss — No Streets to Cross, Just Steps from the Sand! Enjoy breathtaking Gulf and sunset views from your private balcony in this spacious, newly updated condo. Featuring a brand-new bathroom and new flooring throughout, this 4th-floor unit (with elevator access) is the perfect retreat for your Longboat Key escape. The condo comfortably sleeps up to 6 guests. Sip your morning coffee or catch dolphin sightings and stunning sunsets from the balcony with 180° view of the Gulf. Elevator.

4.9 out of 5 average rating, 212 reviews

A spacious living area is highlighted by a large sectional sofa and a wooden coffee table. A TV sits atop a media console, while glass doors provide access to the outdoor patio, allowing natural light to fill the room.

Villa in Lido Key

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

4.99 out of 5 average rating, 191 reviews

A covered patio space is surrounded by lush greenery and decorative plants. A light-colored table and two chairs are arranged on a tiled floor. Large, double doors in a vibrant blue lead to the outdoors, enhancing the welcoming atmosphere.

Guest suite in Sarasota

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Bungalow in Bradenton Beach

A tranquil outdoor space features a wooden dining table surrounded by eight chairs set on a tiled patio. A small, curved swimming pool is framed by lush tropical plants, and umbrellas provide shaded areas. The vibrant greenery creates a serene atmosphere.

4.91 out of 5 average rating, 107 reviews

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

Bungalow in Indian Shores

A serene beachfront scene showcases soft sand and gentle waves under a clear sky. Lounge chairs are arranged in the foreground, while umbrellas and beach tents are visible further along the shoreline. The bungalow's outdoor seating area is seen, surrounded by lush greenery.

4.96 out of 5 average rating, 157 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows + heated pool

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.

4.91 out of 5 average rating, 181 reviews

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 of Mexico 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.

Home in Indian Beach-Sapphire Shores

A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

4.94 out of 5 average rating, 125 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

An oceanfront view is captured from the private lanai, showcasing the serene blue waters of the Gulf of Mexico and a heated pool below. Palm trees frame the scene, and beachgoers can be seen in the distance enjoying the sandy shore.

4.98 out of 5 average rating, 197 reviews

Condo with a View 1: Oceanfront!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located 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 onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Guesthouse in Bradenton Beach

A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.

4.99 out of 5 average rating, 185 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

4.94 out of 5 average rating, 112 reviews

A three-story coastal home is framed by palm trees, featuring a light-colored exterior. A large balcony is visible on the second floor, and the entrance includes a garage and a fenced area. The setting is serene, highlighting the proximity to the beach.

Home in Holmes Beach

The Peachy Beach House, steps to the gulf

Rent two weeks from Aug- Dec receive 15% off Hurricane season refunds possible. Two bedroom, 2 full bathroom, new heated private pool Steps from semi-private gulf beach, this 3 story on a quiet street in N. HB Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new tempurpedic king bed Gulf views from bedrooms. You’ll find: crib, high chair, beach chairs, wagon, canopy, beach toys and towels!

Superhost

A spacious courtyard is highlighted by a heated pool surrounded by palm trees and lounge chairs. Lush green landscaping encircles the pool area, providing a tranquil setting. The exterior of the condominium features large windows, allowing for bright natural light.