Condo vacation rentals in Longboat Key

4.95 out of 5 average rating, 142 reviews

Condo in Sunset Beach

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

NEWLY FULLY RENOVATED breathtaking beachfront condo on private beach. Walking distance to bars, restaurants, live music and more! Brand new king size bed, high speed wi-fi, Smart TVs with cable/Netflix, heated swimming pool, BBQ/Grills, outdoor tables, showers, beachfront balcony, workspace and you are RIGHT on the beach! Short drive to TPA/PIE airports, Downtown St Pete, Dali Museum & more! The condo is fully equipped with everything you need and run by a Superhost for a perfect Beach vacation!

4.93 out of 5 average rating, 119 reviews

A private balcony overlooks the Gulf, featuring seating arranged around a glass-top table. Blue beach chairs are visible on the sandy shore, while the ocean stretches out into the horizon under a clear sky.

Condo in Indian Shores

Beachfront Condo, Heated Pool and SPA!

Renovated direct Gulf front condo with 3 bedrooms and 2 bathrooms. The private balcony overlooking the sugary sand beach of Indian Shores has sliding doors from both the living room and master bedroom. The beach-side master bedroom has a King size bed, sliding glass door to the balcony and an en-suite bathroom. There is a washer and dryer right in the condo. The community features a beach-side heated pool and hot tub. There are two gas grills for you to use. This is a NO Smoking, NO pets condo.

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, 108 reviews

Beachfront Escape – Private Balcony, Gulf 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.

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.

4.93 out of 5 average rating, 120 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.

4.99 out of 5 average rating, 114 reviews

A beachfront balcony features a round table with four striped chairs, inviting outdoor relaxation. The expansive view showcases sandy shores meeting the calm turquoise waters under a clear blue sky. Sliding glass doors provide easy access to the living space.

Condo in Indian Shores

Five Star Beachfront Condo Newly Renovated

A newly transformed beachfront Condo offers five-star accommodations in sleepy Indian Shores, Florida. This is the second renovated unit by a Superhost/owner. This unit is only feet from the beautiful white sand & crystal clear water. The sunsets are epic from the balcony. Several great restaurants & bars are within walking distance of your front door. Amenities include a fully stocked kitchen, heated pool, SmartTV's, high speed Wi-Fi, reserved parking and only minutes from the Tampa airport.

4.99 out of 5 average rating, 162 reviews

Silver Sands: Open Tomm & Thurs, $150/nt + Fees!

This charming seaside condo 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

Condo in Pass-a-Grille Beach

Two beach chairs are placed under a large white umbrella on the pristine white sand. The tranquil blue water of the ocean is visible in the background, complemented by clear skies and palm fronds gently swaying in the breeze.

5 out of 5 average rating, 161 reviews

Beachfront in Pass-A-Grille w/ 2 bikes

Enjoy an intimate and relaxing stay on the best stretch of the St. Pete Beach of Pass-a-Grille. Walk out your door to the white sand towards the famous Don Cesar or dine on your deck facing the water. Free parking, 2 bikes, SUP board, towels, umbrella, beach chairs, & cooler! We are allowed 3 rentals under 28 yearly. Please inquire to see if you are one of the lucky guests to come. We love long term guests but understand not everyone can do this and simply need a little escape! 🤍

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, 191 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 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.

4.97 out of 5 average rating, 119 reviews

The bedroom features a spacious bed with decorative pillows and a light blue throw. An accent bench sits at the foot of the bed, while a round mirror reflects soft lighting from a chandelier. A patterned wallpaper adds a coastal touch, enhancing the serene ambiance.

Condo in Bradenton

KING Bed + Anna Maria Island Beaches + Beach Gear!

⚓️🦩Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

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, 344 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. Enjoy 2 free bikes day rental with booking!

4.98 out of 5 average rating, 190 reviews

A fire table is positioned near large glass windows that frame a stunning sunset over the water. The reflection of the vibrant sunset is visible in the water, while the outdoor landscape is softly illuminated by the fading light.

Condo in Bradenton

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

A living room area features large sliding glass doors that open to a private balcony with views of the Gulf of Mexico. Soft gray furniture is arranged around a coffee table, and a flat-screen TV is located on a media console. Natural light fills the space.

4.88 out of 5 average rating, 117 reviews

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Popular amenities for Longboat Key condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.88 out of 5 average rating, 43 reviews

A wooden coffee table features a rounded design, adorned with a decorative bowl and a small vase containing a fresh green leaf. The background showcases a cozy seating area with neutral-toned cushions and a touch of greenery.

Condo in Anna Maria

Barefoot Mermaid 4, steps to the beach

Condo in Redington Shores

A serene ocean view captures the sun setting on the horizon, casting warm orange and gold hues across the sky. Gentle waves break on the shore, creating a foamy shoreline. The tranquil scene highlights the beauty of nature at dusk.

5 out of 5 average rating, 14 reviews

Beachfront Condo with Stunning Sunset Views

Aerial view captures the pristine beach alongside the expansive manicured grounds of a gated community. The layout features several buildings with red roofs, centered around a heated salt water pool. The shoreline and beach-goers are visible in the distance.

4.98 out of 5 average rating, 48 reviews

Siesta Dunes 1st Floor Beach Front Retreat + Bikes

4.93 out of 5 average rating, 55 reviews

A private balcony overlooks the beach and Gulf of Mexico. Two red chairs are positioned for comfortable seating, while a railing provides safety and unobstructed views. The serene landscape features green grass leading to the sandy shore and the calm blue waters of the ocean.

Condo in Sunset Beach

INCREDIBLE SUNSET BEACH OCEANFRONT TOP FLOOR CONDO

4.9 out of 5 average rating, 31 reviews

A panoramic view of the Gulf of Mexico is visible from the private balcony, featuring a sleek railing and two outdoor chairs. The serene sky meets the ocean horizon, while beach vegetation frames the picturesque shoreline.

Condo in Bradenton Beach

Sandcastle Splash - Beachfront Condo

4.95 out of 5 average rating, 20 reviews

A spacious living area is furnished with a comfortable sofa and two armchairs, all in calming blue hues. Natural light floods the room through sliding glass doors that lead to a private balcony offering views of the beach. A flat-screen TV is positioned across from the seating area.

Condo in Madeira Beach

Chambre 303 - Pool, Hot Tub, Walk to John's Pass!

5 out of 5 average rating, 62 reviews

A dining area is presented with a large wooden table surrounded by blue upholstered chairs. Sunlight pours through expansive windows, revealing views of the turquoise waters and sandy beach beyond. A beach-inspired artwork decorates the wall, adding a touch of coastal charm.

Condo in Sarasota

Breathtaking Beachfront Views in Siesta Key

A bright living area features large glass sliding doors that open to a balcony with ocean views. The space includes a cozy sofa, a sleek dining area, and a kitchen with modern appliances. Natural light fills the room, enhancing its airy feel.

4.97 out of 5 average rating, 30 reviews

Oceanview Penthouse| 1-Min Walk to Beach + Terrace

Pet-friendly condo rentals

A spacious living area features a mix of comfortable seating, including a purple sofa and a black armchair. Large glass doors provide a view of the outdoor space and the surrounding landscape. A dining area is visible with a table set for four, accented by floral decor.

4.88 out of 5 average rating, 52 reviews

Dreamview • 1BR - Siesta Key Beach Sunset View

4.91 out of 5 average rating, 161 reviews

An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

Condo in Treasure Island

Waterside Studio in the heart of TI, walk to beach

Superhost

The balcony area features a pair of sleek white chairs alongside a blue upholstered chair, offering a relaxing space to enjoy coastal views. Glass railings provide an unobstructed sightline to the sandy beach and the shimmering water under a clear blue sky.

Condo in Treasure Island

4.88 out of 5 average rating, 112 reviews

New Beachfront Resort Condo in Paradise

4.76 out of 5 average rating, 471 reviews

A wooden walkway leads through a natural landscape, flanked by tropical vegetation and palm trees. The pathway extends toward the horizon, inviting visitors to the nearby ocean. Soft clouds fill the sky, enhancing the serene setting of Madeira Beach.

Condo in Madeira Beach

Beach Chill Inn #3 - Studio

Superhost

A modern living area features a blue sofa with decorative pillows and a low coffee table. A dining set with white chairs is visible in the background. Bright natural light filters through sheer curtains, enhancing the neutral grey walls and stylish artwork.

Condo in Sarasota

4.86 out of 5 average rating, 128 reviews

Anchor house +6 min. from Siesta Beach+heated pool

Superhost

A set of two white wicker chairs and a small table are positioned on a balcony, providing views of the Gulf of Mexico. The ocean and sandy beach stretch into the distance, with clear blue skies overhead.

Condo in Clearwater Beach

4.9 out of 5 average rating, 397 reviews

Amazing views on beachfront

4.96 out of 5 average rating, 99 reviews

Condo in Holmes Beach

Steps to the beach! Updated Condo at The Terrace

Condo in Clearwater Beach

A welcoming living area is presented with a round dining table and four wooden chairs, positioned near large windows offering views of the waterfront. A ceiling fan adds comfort, while a cozy armchair and side table complete the space, enhancing the serene ambiance.

4.83 out of 5 average rating, 137 reviews

Direct Waterfront "The Lily Pad" Walk to Beach

Condo rentals with a pool

An open-concept living and dining area is highlighted, featuring a white dining table with six chairs, a comfortable seating arrangement, and large glass doors leading to a balcony. A neutral color palette is complemented by a decorative mirror and modern lighting.

4.98 out of 5 average rating, 57 reviews

2 BR condo in Siesta Key w/ Private beach access

4.78 out of 5 average rating, 18 reviews

A beachside area is shown with several white chaise lounges arranged on the sandy surface, facing the ocean. Gentle waves can be seen lapping at the shore under a clear blue sky, accentuated by wispy clouds and coastal grasses in the foreground.

Condo in Bradenton Beach

Beachfront, SPA, Sunsets from the balcony!

4.99 out of 5 average rating, 93 reviews

The balcony features a cozy seating arrangement comprising two chairs and a coffee table, all set against a stunning ocean view. The turquoise waters and sandy beach are visible beyond the railing, offering a serene backdrop for relaxation.

Condo in Sarasota

615 Luxury Condo With Ocean View, Heated Pool +++

5 out of 5 average rating, 10 reviews

An outdoor patio is featured, surrounded by lush greenery and offering a clear view of the sandy beach and ocean. A round table is set with four chairs, while a lounge chair is tucked nearby. A spiral staircase leads to an upper level, enhancing the space's appeal.

Condo in Belleair Beach

Sonrisa 1 - | Beachfront Condo in Belleair Beach

4.9 out of 5 average rating, 49 reviews

The exterior of a multi-story building is depicted, featuring vibrant orange walls and teal shutters. Palm trees line the entrance, and a spacious driveway made of pavers leads to the garage below. The design incorporates balcony spaces and decorative architectural elements.

Condo in Bradenton Beach

Gorgeous Gulf Views - Beachfront 2BR/2B Condo

4.95 out of 5 average rating, 126 reviews

The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.

Condo in Indian Shores

Tropical Beachfront Penthouse-Beach Cottages

Condo in Indian Beach-Sapphire Shores

A circular pool is surrounded by modern white buildings, with palm trees dotting the perimeter. The clear blue water reflects the sky, and a poolside lounge chair is positioned near the edge. Paved stones create a pathway around the pool area.

5 out of 5 average rating, 32 reviews

Chill Sarasota Hideaway

An expansive view showcases the Gulf waters and sandy beach from a fourth-floor corner unit. Lounge chairs are visible on the beach, while a balcony railing frames the scene. Bright skies are complemented by gentle waves rolling onto the shore.