Apartment holiday rentals in Longboat Key

A light-filled bathroom is visible, featuring a modern sink with a glass basin. Towels are neatly hung on the wall. A doorway leads to a bedroom with a spacious bed, complemented by a ceiling fan and natural light flowing through a large window.

4.84 out of 5 average rating, 404 reviews

[Sunny in Siesta] King bed+5 minute walk to beach

Your relaxing beach vacation awaits! Enjoy the island life from a freshly remodeled condo. Quick stroll to the #1 beach in the US. Public Access #12 (5 min walk) or hop on the free trolley to Siesta Beach & the Village. Can’t beat this location...Walk to Crescent Club, Captain Curt’s, Big Water Fish Market, Daquiri Deck & more. Beach gear includes- wagon., 2 chairs, small cooler and beach towels. 2 Bikes available to rent (40 per bike) King bed BEAUTY REST BLACK & queen sofa bed.

Apartment in Madeira Beach

4.98 out of 5 average rating, 104 reviews

Beach Front Madeira Beach

PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away. The condo is walking distance to shopping, banking and many restaurants and bars.

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

4.86 out of 5 average rating, 105 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

A sandy pathway leading to a beach is framed by lush dune vegetation. The scene captures a vibrant sunset over calm waters, with soft clouds reflecting warm hues. Natural light creates an inviting atmosphere, highlighting the serene transition from land to sea.

4.8 out of 5 average rating, 129 reviews

Gulfront Views! BEACHFRONT BARGAIN HUNT NOMINATED

THIS UNIT WAS NOMINATED TO BE FEATURED ON BEACHFRONT BARGAIN HUNT! Unit #102 Features: Full-size kitchen and Gulf-front views Bedding: 1 Queen Murphy Bed and a Sleeper Sofa Savor warm Gulf breezes while resting lavishly in this Gulf-front condo complex. Located directly on the beach, this resort features beautiful Gulf-front views. You are only steps from the white-sand beaches, placid turquoise waters and beautiful sunsets that will have you daydreaming about your next beach vacation.

4.98 out of 5 average rating, 233 reviews

Island Time!

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...!

Apartment 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, 166 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.

4.89 out of 5 average rating, 214 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.

The outdoor area features a heated pool with a rock waterfall, surrounded by lounge chairs. A thatched Tiki hut provides shaded seating, set within tropical landscaping. The villa's light blue exterior and white furnishings enhance the inviting atmosphere of the space.

4.94 out of 5 average rating, 156 reviews

Blanco at Sunset Villas on Anna Maria Island

Back Open Jan '25! Located just 200 steps from the beach you’ll have your feet in the sand in no time. A comfortable living area + fully equipped kitchen. Furnished with island décor and local art. Everything you need including a heated pool, large patio with a Tiki hut, tropical gardens, plus a private outdoor area with a shower for your comfort. Walk to everything – grocery, pharmacy, ice cream, breakfast, pizza, donuts, and the beach which is less than 2 minutes away.

4.97 out of 5 average rating, 145 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.

Apartment 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!

4.88 out of 5 average rating, 131 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, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

An enclosed terrace features a dining table surrounded by white chairs, offering expansive views of Sarasota Bay. Palm trees sway gently outside, while boats are visible in the distance. Natural light floods the space through large glass windows, creating a serene atmosphere.

4.97 out of 5 average rating, 70 reviews

Secluded Bayside Gem with beautiful bay views

Sat to Sat Check in/out 7 day minimum rentals only. Jan-April we do not accept reservations with children of any age. Additional 6% Manatee County tax not included need to collect separately. Newly added Pickleball courts on premises. This secluded, beautifully decorated, bay front condo has expanded views of the Sarasota Bay. 2 min drive to the quiet, unspoiled white sand beaches of the Gulf of Mexico, short distance to great water front dining.

An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.

4.87 out of 5 average rating, 198 reviews

The Beach Condo #107 Beachfront Full View

Unit #107 has private beach access. Only a few steps to the beach will full gulf view. This end condo unit is quiet, ground floor . It is a small studio: new queen murphy bed and queen sofa bed. No separate bedroom. Limited initial limited supply of products/soaps/towels. Common use W/D across from unit. This is a small studio at 330 sq ft. It has been recently remodeled. Grounds, unit, pool recently renovated due to hurricanes.

Popular amenities for Longboat Key apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.91 out of 5 average rating, 64 reviews

A cozy deck area features outdoor seating with two bar stools and a small table adorned with flowers. Palm trees provide shade while a serene waterfront view is visible, with a private dock and a pool in the background.

Apartment in Sarasota

Siesta K- Kayak, Boat Dock, Pool, & walk to Beach

4.9 out of 5 average rating, 50 reviews

Tradewinds Deluxe North Cottage

Apartment in Belleair Beach

A sandy pathway leads to a tranquil beach, flanked by lush greenery and coastal plants. Gentle waves can be seen in the distance under a clear blue sky, creating a serene atmosphere that invites relaxation.

4.92 out of 5 average rating, 62 reviews

Beachfront Oasis / Pool, Beach Access & Ocean View

A spacious living area features a modern sectional sofa with plush cushions in neutral tones. A circular coffee table rests on a soft area rug. A vibrant grass wall adds a touch of greenery, while a dining table with chairs is visible in the background.

4.98 out of 5 average rating, 65 reviews

Luxury 2BR Oceanfront Condo + Rooftop Patio

4.96 out of 5 average rating, 25 reviews

New! Beachfront Paradise! ~Heated Pool! Top Floor

4.98 out of 5 average rating, 45 reviews

Apartment in Sarasota

Charming Poolhouse · 1BR · Close to Siesta

5 out of 5 average rating, 16 reviews

Apartment in Sand Key

CBC 1-3G – 5 Balconies- Gulf & Intercoastal Views!

Apartment in Redington Shores

4.94 out of 5 average rating, 32 reviews

Beachfront with Oceanview Balcony in Quiet Area

Pet-friendly apartment rentals

4.95 out of 5 average rating, 108 reviews

A sandy pathway leads to the beach, framed by lush greenery and tall grasses. The gentle waves of the ocean are visible in the distance, with a clear blue sky overhead. Sunlight casts a warm glow on the pathway, inviting relaxation.

Apartment in Venice

Short walk to beach 4, King bed, Dog Friendly

Apartment in St. Petersburg

A sunset is captured over the intercoastal waterway, with warm hues reflecting on the water's surface. Silhouettes of palm trees line the foreground, while distant markers indicate the waterway's navigation. The scene conveys a tranquil ambiance, enhanced by the fading light.

4.91 out of 5 average rating, 196 reviews

Heron's Hideaway- Studio by the bay!

4.97 out of 5 average rating, 202 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.

Apartment in Bradenton

Luxury 3/3 Margaritaville Resort

A modern living area features a comfortable sectional sofa, accented by textured cushions. A flat-screen TV is mounted on the wall above a wood panel, while large sliding doors invite natural light and provide access to the patio. Indoor plants add a touch of greenery.

4.84 out of 5 average rating, 141 reviews

Siesta Key Condo: Beach, Pool & Village Fun!

Apartment in Belleair Beach

A balcony view that captures the tranquil beach scene, featuring soft pastel hues in the sky. A round table with intricate design sits next to two woven chairs. Below, umbrellas dot the sandy beach, while gentle waves touch the shore.

4.71 out of 5 average rating, 522 reviews

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

Superhost

A cozy living area features a blue sectional sofa accompanied by decorative pillows and a side table with a lamp. A wall clock adds a modern touch, while large sliding glass doors offer views of the outdoor space. A dark blue accent chair complements the scene.

Apartment in Sarasota

4.88 out of 5 average rating, 179 reviews

Lake View 1BR Condo | Heated Pool Near Siesta

Apartment in Indian Shores

Two wicker chairs with cushions are positioned around a small table on a balcony overlooking the beach. The expansive view reveals the Gulf of Mexico and a clear sky with scattered clouds. Beachgoers can be seen in the distance enjoying the shoreline.

4.81 out of 5 average rating, 110 reviews

Casa de B.O.B ... Best on Beach

Apartment in Clearwater Beach

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.

4.9 out of 5 average rating, 450 reviews

Amazing views on beachfront

Apartment rentals with a pool

A clear, inviting pool is surrounded by a landscaped area with tropical plants and palm trees. The bright orange exterior of the building contrasts with the lush greenery. Chaise lounge chairs are positioned nearby for relaxation.

4.96 out of 5 average rating, 50 reviews

Siesta Key Village, Pool, Beach Access 4-min Walk

An aerial view captures the lush greenery surrounding the property, with the sparkling bay visible to one side. The coastline extends in the distance, displaying a serene beach area. The location is highlighted as a short walk to both the beach and bay views.

4.93 out of 5 average rating, 72 reviews

AMI Condo w/heated pool, water view, walk to beach

Apartment in Sunset Beach

A balcony view reveals a serene beach scene, featuring gentle waves lapping at the shore. Lush greenery is present in the foreground, accompanied by a wooden boardwalk leading to the beach. Two chairs and a small table are visible on the balcony, inviting relaxation.

5 out of 5 average rating, 14 reviews

LandsEnd Top Floor Beach Front with Stunning Views

Superhost

A private balcony offers views of the tranquil Gulf of Mexico, with lush greenery bordering the shoreline. A table with a vase of flowers is visible, inviting relaxation. The swimming pool can be seen below, along with chaise lounge chairs arranged for sunbathers.

4.76 out of 5 average rating, 85 reviews

Amazing beachfront View & balcony on Long Boat Key

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, 374 reviews

On the Beach; Siesta Key SunBum Studio

A bright and airy living space features light blue sofas and coastal decor. A television is positioned on a white entertainment unit, with views of the screened balcony visible through sliding glass doors. Potted plants add a touch of greenery to the space.

5 out of 5 average rating, 7 reviews

Island time at Runaway Bay by A Shore Thing Vacati

4.94 out of 5 average rating, 47 reviews

Bayside Luxury Condo with Pool! Walk to Bridge St

A spacious living area features comfortable blue sofas adorned with decorative cushions. A wooden coffee table occupies the center of the room, surrounded by a light area rug. Natural light streams through large windows, enhancing the airy atmosphere, while a ceiling fan adds to the comfort.