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Apartment holiday rentals in Caladesi Island

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Top-rated apartment rentals in Caladesi Island

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Top guest favourite
The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.
Apartment in Madeira Beach

Rincón Divino MB 2 Balconies, Ocean & Marina Views

EXCLUSIVE: Saturday checkout is at 5pm. This condo features 2 private balconies, w/ spectacular ocean & marina views. It's stylish decor, meticulously picked quality & comfortable furnishing/accessories are sure to please. It’s conveniently located just across the street from the pristine white sands and sunsets of the Gulf of Mexico. It is adjacent to the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool, hot tub, fitness room & event center.

ValueFamilyTV

4.99 out of 5 average rating, 243 reviews
Top guest favourite
An inviting living area showcases a comfortable blue couch with a colorful throw blanket. A wooden dining table is positioned nearby, and natural light flows through expansive glass doors leading to a balcony with a glimpse of trees and water outside.
Apartment in Indian Rocks Beach

Beachside, Lux, 3 Minute Walk, Views Fam.-Friendly

Completely remodeled luxury beachside condo with balcony. Water/beach view- balcony and living room. Short walk down to beach. Saatva Luxury mattress in Master. 2nd Bed- has double over double bunk bed with twin trundle. Couch -pullout bed that sleeps two more. Kid-friendly! Pack n play with memory foam mattress and diaper genie. Toys, child-proofing, kid utensils etc in unit. Beach supplies, towels, wagon, chairs, toys umbrellas.. below in storage. Paddleboard and bike rental available nearby!

ValueLocationAccuracy

4.95 out of 5 average rating, 129 reviews
Top guest favourite
A scenic view of a fishing pier extends into the water, framed by gentle waves and a sandy beach. The sky is filled with colorful clouds, reflecting hues of orange and blue as the sun sets on the horizon.
Apartment in Clearwater Beach

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!

Stylish & Sunny Corner Unit On Dolphin Faved Inlet Across The Street From Florida's #1 Beach. This all-inclusive unit allows you to walk everywhere and enjoy all Clearwater Beach has to offer from sand & sun to restaurants & shopping. Updated & upgraded 3 bedroom, all with connected bathrooms offers amazing space, a chef's kitchen as well as bright & beautiful dining & living rooms. Private balcony to relax & watch the sunset. Beach concessions include sea kayaks, jet ski's, boating & more.

ValueFamilyQuiet

4.98 out of 5 average rating, 182 reviews
Guest favourite
A private balcony is seen featuring two white chairs and a table, offering uninterrupted views of the Gulf of Mexico. The calming blue sky meets the horizon, enhancing the serene beachfront experience.
Apartment in Clearwater Beach

Beachfront in exclusive resort

This upper floor, 3-bedroom modern chic condo hotel suite offers sweeping views of the Gulf of Mexico from private balconies. While preparing your morning coffee on the spacious kitchen island, you can see the shrimp trawlers making their way out to sea. Enjoy a cocktail while watching the sunset over the open water of the Gulf of Mexico. This suite can sleep 8, with King or Queen-size beds in each of the three bedrooms, a comfortable full-sized sofa bed in the living room & 3-1/2 bathrooms.

LocationFamilySleep quality

4.91 out of 5 average rating, 337 reviews
Guest favourite
An aerial view displays the beachfront condominium alongside Indian Rocks Beach, highlighting white sandy shores and a tranquil atmosphere. People can be seen enjoying the beach, with colorful umbrellas scattered across the sand. The proximity of the property to the shoreline is prominently featured.
Apartment in Indian Rocks Beach

Modern, Luxurious Beach Condo -Steps To The Beach!

Come enjoy your piece of paradise on this luxurious, newly renovated beach condo, just 40 steps from the beach! The condo has two bedrooms with two private baths, and a living space with an extra half bathroom. The recently updated kitchen has new stainless steel appliances, granite countertops, and a spacious breakfast bar. The living room has a 51 inch TV and 2 leather pull-out couches. Free private parking for two cars. Beach chairs, umbrellas, towels and 2 bicycles are included!

LocationValueHospitality

4.87 out of 5 average rating, 403 reviews
Guest favourite
A bright living area features a modern, light-colored sectional sofa and a round coffee table. A comfortable armchair is placed nearby. Large glass doors lead to a private balcony, enhancing views of the waterfront. A ceiling fan and wall-mounted TV are also visible.
Apartment in Belleair Beach

BBC216 - Gulf Breezes & Beachfront Vibes!

🌊 Gulf-Front Condo w/ Balcony | Beach Access | Pool | Sleeps 6 🌴 ~ Managed by Sandy Feet Vacation Rentals ~ ✨ Relax on Your Private Balcony with Stunning Views of Belleair Beach! ✨ Unwind in this beautifully updated boutique beachfront condo located at the exclusive Belleair Beach Club—just minutes from the white sands of Clearwater Beach. Whether you're here for a romantic getaway or a family vacation, this coastal gem offers the perfect mix of comfort, style, and location.

LocationFamilyOutdoor spaces

4.84 out of 5 average rating, 111 reviews
Guest favourite
A spacious bed is positioned in front of large windows offering views of the Gulf of Mexico. Soft blue accent pillows complement the bedding. Outside, two chairs on the balcony overlook the sandy beach, creating a serene coastal ambiance.
Apartment in Clearwater Beach

#1- SALE! Nice 2/2 Condo-Directly on the sand!

Kick back and relax in this calm & quiet beachfront condo, located directly on beautiful North Clearwater Beach! Unit is located on the 2nd floor with gorgeous views of the Gulf of Mexico. 2 Bedrooms, 2 bathrooms with a private balcony overlooking the beach. Sleeps 6 with the air mattress. WiFi included, Smart TV's, beach chairs, towels, toys, etc. Just bring yourselves and you are ready to go! Fully equipped full-sized kitchen with enough supplies to get you started!

ValueLocationIndoor spaces

4.95 out of 5 average rating, 108 reviews
Guest favourite
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.
Apartment in Belleair Beach

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

RECENTLY RENOVATED. This cozy 1 bedroom condo with a kitchen in Belleair Beach just steps from the sugar-white sand and crystal clear waters that are consistently ranked among America's most beautiful beaches! It has a lovely pool area that overlooks the gulf with a patio, chairs and grills. You’ll love the beachfront views and quiet ambiance. 3rd Floor, balcony with DIRECT BEACH/GULF VIEW. Minutes away from Clearwater Beach. Perfect for couples! ONE parking spot.

LocationValueBeach

4.72 out of 5 average rating, 548 reviews
Guest favourite
Apartment in Indian Rocks Beach

Beachfront Condo | Gulf Views & Stunning Sunsets

Wake up to the sound of the waves and breathtaking Gulf views from this beautifully updated beachfront condo on the sugar-white sands of Indian Rocks Beach. This inviting 2-bedroom, 2-bath retreat features renovated bathrooms, unobstructed ocean views, and a private balcony perfect for morning coffee or unforgettable sunsets. Steps from the beach, it's the perfect escape for couples, families, and friends seeking the ultimate Florida Gulf Coast getaway.

ValueFamilyPool

4.82 out of 5 average rating, 104 reviews
Top guest favourite
Apartment in Indian Rocks Beach

On Private Beach! Full Kitchen, Ground Level Unit5

Fully remodeled in 2025! We are back and better than ever! On the Private Beach! Breathtaking Gulf views! 2 bedroom 1 bath unit +bunkbeds & patio leading to private beach, full kitchen 2 queen beds plus twin bunkbed. Sleeps 6 guests. We furnish linens, towels, toiletries, beach towels, beach chairs. 1 Free parking space included. See our 1 bedroom units, same location, Gulf Dreams unit 6 & Tide Vibes unit 7.

ValueLocationShared spaces

4.91 out of 5 average rating, 121 reviews
Top guest favourite
A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.
Apartment in Indian Rocks Beach

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

LocationFamilyBiking

4.98 out of 5 average rating, 170 reviews
Guest favourite
Apartment in Indian Shores

Panoramic Gulf View Beachfront Condo

Escape to our 7th-floor beachfront condo at Sand Castle II in Indian Shores! This spacious 3-bedroom, 2-bath sanctuary comfortably sleeps 8. Enjoy panoramic Gulf views from your private balcony, perfect for watching dolphins. With direct beach access, a heated pool, and a hot tub, this is the ultimate coastal getaway. Walk to Caddy's for dinner and live music!

FamilyLocationView

4.93 out of 5 average rating, 153 reviews

Popular amenities for Caladesi Island apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Guest favourite
Apartment in Indian Rocks Beach

Beachfront corner condo 3 bedroom, 2 bathroom.

FamilyValueQuiet

4.82 out of 5 average rating, 127 reviews
Top guest favourite
A spacious living room features a large sectional sofa adorned with decorative cushions, providing a comfortable seating area. A coffee table with a natural wood finish is central to the room. Sliding glass doors open to a balcony, revealing views of the beach and ocean.
Apartment in Indian Rocks Beach

Work Remote & Stay Beachfront

LocationFamilyQuiet

5.0 out of 5 average rating, 122 reviews
Top guest favourite
An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.
Apartment in Treasure Island

Spectacular beach to bay views from this resort.

LocationFamilyComfort

4.99 out of 5 average rating, 231 reviews
Top guest favourite
A bright and airy living area features a light-colored sofa adorned with decorative pillows, complemented by a stylish round table set for two. Large windows allow natural light to fill the space, showcasing a modern kitchen equipped with updated appliances.
Apartment in Dunedin

Quiet Locale King Beds 1 Mile To Honeymoon Island

FamilyValueHeating

4.94 out of 5 average rating, 31 reviews
Top guest favourite
A spacious studio features a king-sized bed with a woven headboard, bedside lamps providing soft illumination. A kitchenette is visible, equipped with wood cabinets and modern appliances. Light-colored flooring and bright walls create a fresh atmosphere, with a canvas showing beach chairs adding a coastal touch.
Apartment in Dunedin

Studio King Sunset at Beso Del Sol (Pool/Hot Tub)

ValueLocationParks

4.95 out of 5 average rating, 56 reviews
Superhost
Apartment in Clearwater Beach

2BR Ground Floor Beach Condo + Heated Pool Access!

ValueLocationKitchen

4.68 out of 5 average rating, 53 reviews
Guest favourite
An open living area showcases large sliding glass doors with stunning ocean views. A comfortable seating arrangement features a dark leather couch and coordinating throw pillows. A modern ceiling fan hangs above, while a dining table is set with a centerpiece and blue accents.
Apartment in Indian Rocks Beach

Sea Side Sunsets Unit C

LocationFamilyCondition

5.0 out of 5 average rating, 37 reviews
Guest favourite
A spacious wooden deck offers lounging chairs facing the beachfront. The uninterrupted view of the Gulf of Mexico extends to the horizon under a bright blue sky, while gentle waves lap against the shore. Lush greenery borders the beach, enhancing the coastal scenery.
Apartment in Belleair Beach

Beachfront Belleair Beach Condo Est. rental 2016

FamilyLocationKitchen

4.97 out of 5 average rating, 34 reviews

Pet-friendly apartment rentals

Superhost
The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.
Apartment in Treasure Island

Beachfront Condo in Exclusive Resort

FamilyLocationHospitality

4.86 out of 5 average rating, 674 reviews
Guest favourite
A bright bedroom features a spacious bed adorned with light blue and white striped linens. Natural light floods the room through sliding glass doors that lead to a private balcony with an ocean view. Two decorative lamps and a textured area rug enhance the serene atmosphere.
Apartment in Sunset Beach

2 Story Penthouse | Pool | Balcony | Gulf View 602

FamilyLocationBack garden

4.89 out of 5 average rating, 160 reviews
Top guest favourite
Apartment in Indian Rocks Beach

Walk to Beach, Bars, and Restaurants Nearby

ValueLocationPool

4.85 out of 5 average rating, 125 reviews
Guest favourite
A spacious open-concept living area includes a sleek kitchen with modern appliances and ample counter space. A dining table with six chairs and a pool table provide options for entertainment. Bright overhead lights create a welcoming atmosphere, with light-colored cabinets complementing the room.
Apartment in Redington Beach

Penthouse,intercoastal, 3/3 views/heated pool

LocationFamilyCondition

4.94 out of 5 average rating, 118 reviews
Top guest favourite
Gentle waves lapping against a sandy shore create a serene coastal scene. The sky is filled with wispy clouds and varying shades of blue, reflecting the tranquil atmosphere of the beach. The shoreline reveals patterns in the wet sand as the water recedes.
Apartment in Clearwater Beach

Steps 2 beach! Beachy and Luxurious! Easy Living!

LocationFamilyAccess

4.95 out of 5 average rating, 346 reviews
Top guest favourite
A modern kitchen area features a large island with seating, complemented by white cabinetry and gleaming countertops. Natural light floods the space through expansive sliding glass doors, which lead to a private terrace with ocean views. A comfortable seating area is arranged nearby.
Apartment in Treasure Island

Luxury Seashell Oceanfront Condo with Pool

FamilyValueSleep quality

4.9 out of 5 average rating, 119 reviews
Top guest favourite
A serene swimming pool is bordered by palm trees, with lounge chairs positioned around the edge. The pool area is complemented by views of the water and lush greenery, creating a tranquil outdoor escape.
Apartment in St. Petersburg

Sunny St. Pete Getaway with Dolphins

LocationFamilyComfort

4.87 out of 5 average rating, 122 reviews
Top guest favourite
A comfortable living area features a round dining table set for four, surrounded by modern chairs. Two seating areas include plush armchairs and a sofa, complemented by a tropical plant. Large windows offer natural light and views of the outdoor scenery.
Apartment in Madeira Beach

Penthouse Condo on Water Steps to Beach+Johns Pass

FamilyLocationCheckout

4.97 out of 5 average rating, 103 reviews

Apartment rentals with a pool

Top guest favourite
A cozy sitting area is featured on the private balcony, highlighted by a circular rattan chair adorned with soft cushions. Green plants provide a touch of nature, while water views and boats can be seen beyond the railing, enhancing the relaxing atmosphere.
Apartment in Clearwater Beach

Waterfront Condo | Steps to Clearwater Beach 2King

ValueLocationQuiet

4.99 out of 5 average rating, 147 reviews
Guest favourite
A vibrant water park area features colorful water slides curving overhead, with a rocky structure resembling a pirate ship in the foreground. The clear blue water in the pool invites guests to enjoy a refreshing experience, framed by lush greenery and sunny skies above.
Apartment in Indian Rocks Beach

Waterfront, Harbourside, Water Park, Beach, #8819

LocationFamilyAccuracy

4.87 out of 5 average rating, 195 reviews
Guest favourite
Vibrant water slides in various colors are positioned above a pool area. A playful shark sculpture is featured near the pool's edge. Lush tropical plants frame the scene, and the clear blue sky complements the exciting atmosphere of the water park.
Apartment in Indian Rocks Beach

Waterfront, Harbourside, Water Park, Beach, #8817

LocationValueParking

4.83 out of 5 average rating, 269 reviews
Guest favourite
Apartment in Belleair Beach

Condo On The Beach - Ocean View Balcony - Pool

ValueFamilyWifi

4.81 out of 5 average rating, 123 reviews
Guest favourite
A comfortable living area is presented with a spacious sectional sofa adorned with decorative pillows. A large flat-screen TV is mounted on a wooden accent wall, enhancing the cozy atmosphere. The open layout leads towards a bright kitchen visible in the background.
Apartment in Indian Rocks Beach

Golf Cart, 2 bed 2 Bath, Heated Pool

ValueLocationGetting around

4.9 out of 5 average rating, 148 reviews
Top guest favourite
A balcony space is shown with two white lounge chairs positioned facing the ocean. The beach and turquoise waters are visible in the background, complemented by a clear blue sky. The glass door provides seamless access to the indoor area.
Apartment in Indian Shores

Relax in a Newly Renovated Beach Front Paradise

FamilyLocationWalkability

4.98 out of 5 average rating, 139 reviews
Guest favourite
Apartment in Madeira Beach

Beach Front Gulf View at John’s Pass Medeira Beach

ValueLocationGetting around

4.9 out of 5 average rating, 135 reviews
Guest favourite
A bright living area is furnished with comfortable couches and a round coffee table. A flat-screen TV is mounted on the wall across from the seating. Natural light enters through large windows and a door leading to the patio. Decorative items are placed on shelves.
Apartment in Indian Rocks Beach

Beautiful condo on the beach with heated pool!

FamilyLocationCheck-in

4.91 out of 5 average rating, 137 reviews

Destinations to explore