Vacation rentals in Holiday

Home in Indian Rocks Beach

The image showcases a serene beach scene with soft white sand in the foreground, gently lapping waves in a range of turquoise and green hues, under a clear blue sky featuring wispy clouds. The tranquil waters stretch to the horizon.

4.99 out of 5 average rating, 166 reviews

Luxe BeachHouseA Heated Pool, 2 min walk to Beach

CarlaRating, 5 stars2 weeks ago

My family and I were extremely satisfied with our stay! The location to the beach was phenomenal~ the ability to come back and have a pool and hot tub was an added bonus! The home worked out perfect for us ~ the beds were comfortable and the pictures match exactly what you will find! The view of the sunset was stunning from the rooftop, too! We would stay again~

Apartment in Clearwater Beach

A cottage is set amidst vibrant tropical landscaping, featuring palm trees and lush bushes. A stone pathway leads to the entrance, bordered by well-maintained grass and colorful plants, under a clear blue sky, creating a serene outdoor environment.

5 out of 5 average rating, 3 reviews

LAZY LEMON COTTAGE 2 pools steps from the beach!!!

PriscillaRating, 5 stars13 months ago

The Lazy Lemon was perfect for our getaway. We didn't have to drive anywhere, we were able to just walk anywhere. Close to restaurants, shopping and the beach! We brought our boat and this place was just around the corner from the boat ramp. We will definitely be back! James was a wonderful host and reponded very quickly.

5 out of 5 average rating, 9 reviews

A modern kitchen is seen, featuring white cabinetry and stainless steel appliances. The island offers seating with dark chairs, while a range of cooking utensils is organized on the countertop. Bright overhead lighting enhances the space, and a doorway leads to a nearby room.

Home in Largo

Red's Bungalow

DawandaRating, 5 stars1 month ago

This was actually better than the pictures The home was absolutely adorable, very clean & inviting. The location was close to everything. The beach was 5min away. Restaurants were very good. Lisa was very considerate about any concerns you may have. My family enjoyed everything about this rental. The outside area was also very nice fenced in backyard. I would definitely recommend renting this wonderful home. I will be back.

4.93 out of 5 average rating, 54 reviews

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

Home in Palm Harbor

Private pool, Golf Cart, Completely Renovated!

OlalekanRating, 5 stars4 days ago

Jarrett's place was exactly as described as posted. The house was very welcoming and adequate for our spring break stay. He was very responsive when needed; its a great choice for families with the backyard pool and games. I will definitely recommend to others. Thanks for the accommodation.

Cottage in Indian Rocks Beach

A charming cottage exterior is highlighted by vibrant blue accents on the door and window frames. Lush palm trees surround the property, and a pathway of red bricks leads to the entrance. Gravel landscaping complements the home, enhancing its welcoming appearance.

4.7 out of 5 average rating, 208 reviews

Beachy Paradise

Rama RaoRating, 5 stars1 week ago

We were a family of 3 with one toddler aged 3. The check-in and check out was a breeze. We were comfortable in the queen bed as our toddler sleeps with us but would be great if the bed was king. The place was clean and well maintained inside. The location is wonderful, it was lively and is right next to a park. Our toddler had a good time having fun at the park as it’s just a few steps away. There are quite a few restaurants so food is very easy to find. But if you are on a tight budget you would need to drive from 7-15 minutes to get the big franchise foods. The area is very peaceful and felt very safe walking at nights. The house comes with beach chairs and laundry along with a shower outside the house. So going to the beach and spending time at the beach is very easy as it’s also just a few minutes walk. I see this property having a lot of potential with some tweaksthat would make it even wonderul for small familieis and couples. Overall we had a very pleasant stay and recommend it

Cottage in Indian Rocks Beach

A view of the beach is captured from a balcony, showcasing vibrant turquoise waters and a sandy shore. Sunbathers and colorful umbrellas dot the beach, while charming coastal cottages frame the scene. The image conveys a relaxed atmosphere, with soft ocean waves visible in the background.

5 out of 5 average rating, 42 reviews

Upper Deck prime area no condos/crowds

AshleyRating, 5 stars1 week ago

I can’t say enough of how much we enjoyed this cozy cottage. The setting is idyllic and we wished we could stay for a month. The house had everything we needed and our family of 4 was very comfortable. We loved being able to go back and forth to the beach and we enjoyed exploring the surrounding areas. I also really enjoyed the character of being in an older home and the cottage is even more adorable and bright in person.

4.86 out of 5 average rating, 147 reviews

Apartment in Clearwater

2 Bed Clearwater Vacation Condo.

EllinorRating, 5 stars5 months ago

We had a great stay in this apartment, which had everything we needed in order to make our holiday comfortable and satisfactory. Amenities and planning corresponds well to the description and photos. The location is a great starting point to discover the neighborhoods as well as surrounding cities and sights. The grocery store as well as some restaurants are within walking distance from the apartment. Anastasios and Gary are very responsive and informative both prior- as well as under our stay, which was much appreciated. I can only give my best recommendations for this place. We hope to come back again one day soon.

0 of 0 items showing

What guests are saying

Brand new home, Modern design, Close to Beaches

4.83 out of 5 average rating, 12 reviews1 month ago

Hun’s property is in a terrific location on a quiet street. It is close and convenient to beaches, shopping, and restaurants. The house is all new construction, clean, and well appointed. My husband and I felt very comfortable there and had a great stay. Hun was particularly responsive the times I had to reach out to him. It would be a pleasure to stay at this property again.

Home in Largo

What guests are saying

NEW! The Seaside Retreat (FREE heated pool)

4.99 out of 5 average rating, 85 reviews1 month ago

This home was as clean, if not more, than some of the nicest places, even hotels, that we have stayed at. Updated beautifully, you couldn't convince me that some of the work wasn't completed yesterday, it was immaculate. We traveled with our toddler, and Nancy already had a pack and play, highchair, appropriate sized life vests, and toys. We felt welcomed and comfortable. The pool area is gorgeous and spacious, we enjoyed the heated pool daily. Even on a chilly (66 degree) day, we still swam. A short distance to Tampa, we recommended planning to eat most meals in the Tampa area, as around Apollo Beach we were disappointed by the selection. Not the hosts fault! We would readily stay again, just would have needed to pick up more groceries to cook (publix is close!) or plan better for meals out. We enjoyed the Florida Aquarium in Tampa, the Manatee Observation in Apollo Beach, and even took a day trip to Anna Maria Island. We enjoyed our stay thoroughly and look forward to visiting again.

Home in Apollo Beach

What guests are saying

Direct Oceanfront with 180 degree view BOOK NOW!

4.97 out of 5 average rating, 39 reviews1 month ago

Great hosts. Great communication. Place was lovely!!! Very comfortable. Host made arrangements for a different and comparable place immediately after the condo association unexpectedly closed our original place to stay for repairs from hurricane damage. We weren’t notified that the pool hadn’t been reopened (at either place). The pictures showed a functional pool and nothing that indicated it was closed. The kids were disappointed but this gave us all more beach time which is why we were there in the first place. I’m sure this was just an oversight after all the devastation that occurred there last summer. Can’t imagine what that was like. Thankful we could come back.

Home in Madeira Beach

What guests are saying

Coastal Getaway~Spacious~ 5 min to Madeira Beach!

5 out of 5 average rating, 61 reviews5 days ago

Amelia’s house is better than the photo’s and a lovely, comfortable place to stay. It is extremely well equipped, especially for visiting the beach and if you have little ones, they will love the play room and safe grassed back garden. It is an easy and quick 6 minutes to Madeira beach and only 5 minutes to the nearest Publix supermarket. Amelia is also a quick and responsive host. It’s no surprise that the reviews are so glowing.

Home in Seminole

What guests are saying

Beach Cottages Ocean & Pool View Condo!

4.76 out of 5 average rating, 17 reviews8 months ago

Perfect 3 day trip. Covered parking was appreciated. Nice balcony access from both the master bedroom and the living area.... if your not on the beach its the next best place to watch the sunset. Very nice kitchen area. A quick trip (by car) to Publix gave us the opportunity to stock the refrigerator and create some amazing meals to enjoy in the dining area or on the good sized balcony table. The kitchen was well furnished with all the cookware, utensils etc. needed. From our parking area directly under the building you exit a coded gate that gives you immediate access to the real reason for visiting here....toes in the sand, a welcoming breeze, the calming sounds of the surf, and the opportunity to "exhale" from the rigors of life....

Condo in Indian Shores

What guests are saying

Beachfront Bliss! Directly on Gulf with pool!

5 out of 5 average rating, 27 reviews3 months ago

We had an absolutely amazing vacation at Bliss and Gary’s place. From the minute we arrived until the minute we left we felt like we were home, with an amazing ocean view. Wonderful location, phenomenal amenities and the best hosts you could ever ask for! Anything you needed they were only a text away. We will definitely be returning and recommending this little slice of heaven to all our friends!

Condo in Indian Rocks Beach

1 of 12 pages

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Holiday vacation rentals

Laptop-friendly workspace

Stay near Holiday's top sights

Miss Vicki's On The River37 locals recommend

La Fondita de Leo10 locals recommend

Publix Super Market at Holiday Centre8 locals recommend

PK's PlayZone & Grille4 locals recommend

Dunkin'3 locals recommend

ALDI3 locals recommend

Other great vacation rentals in Holiday

4.97 out of 5 average rating, 31 reviews

The exterior of the home features a spacious driveway leading to a two-story structure with a charming balcony. Lush greenery and manicured landscaping enhance the inviting curb appeal, complemented by soft sunset colors illuminating the sky.

Home in Palma Ceia

SouthTampa-Family&Group Oasis-3K bd, private pool

ChristopherRating, 5 stars1 month ago

Great house in a wonderful neighborhood. Recommend for families looking to check out a game or do any of the wonderful things available to do in Tampa!

4.9 out of 5 average rating, 72 reviews

The exterior of the house features a two-story design with large windows allowing for natural light. Soft outdoor lighting highlights the entrance, while a neatly landscaped yard with palm trees creates an inviting atmosphere. The driveway leads to a two-car garage.

Home in Riverview

2 Story comfort beautiful home with all amenities

JamesRating, 5 stars2 months ago

I had an incredible experience at this Airbnb! The home had everything I needed for a comfortable stay. The location was perfect—peaceful yet close to everything I needed. I would absolutely stay here again and highly recommend it to anyone looking for a top-notch Airbnb experience. Thank you Edgar!

Home in Old Seminole Heights

A modern kitchen is showcased with white cabinetry and a spacious granite countertop. Stainless steel appliances reflect light, while large windows bring in natural light. The marble-like tile flooring adds elegance, and a potted plant provides a touch of greenery.

5 out of 5 average rating, 16 reviews

Poolside Paradise with Basketball Court

SkylarRating, 5 stars1 week ago

5 stars! Everything about our stay was absolutely perfect. The host was incredibly accommodating and thoughtful—they truly thought of everything to make the space feel just like home. From the moment we walked in, we felt welcomed and cared for. The beds were incredibly comfortable—we slept so well each night, which is such a rare find when traveling! They didn’t miss a single detail. Every little thing we could’ve needed was already there, making our stay effortless and relaxing. You can tell they genuinely care about their guests’ comfort and experience. On top of it all, they were beyond kind and so responsive to any questions we had. We 100% recommend this place to anyone looking for a cozy, well-cared-for stay—and we will absolutely be back! Love how they are transforming this area and the love and energy they are pouring into all the surrounding homes. Oh, and the noise level at night… NONE which was very important to us. Love this place!

Apartment in Indian Rocks Beach

4.8 out of 5 average rating, 273 reviews

Enjoy brand new vacation 2/2 condo & water park!

KellyRating, 5 stars3 weeks ago

Host was very responsive to questions before and during our stay. This was our first time renting an Airbnb so that was so helpful. This is a great condo with easy access to the beach, restaurants, shops and more.

4.9 out of 5 average rating, 79 reviews

A modern kitchen features a large marble island with four black bar stools. Stainless steel appliances are integrated with sleek white cabinetry, and a textured stone backsplash adds detail. Natural light filters in through large windows, illuminating the elegant tile flooring.

Home in Tampa

Enjoy every moment

EvanRating, 5 stars3 days ago

The place was just like the pictures. Very new and clean. The pool area was great. Would recommend.

4.77 out of 5 average rating, 30 reviews

A modern kitchen features white cabinetry with sleek handles and a spacious countertop. Stainless steel appliances, including double ovens and a cooktop, are integrated into the design. Under-cabinet lighting adds a bright ambiance, highlighting the elegant marble backsplash.

Home in Holiday

Luxurious holiday home

RichardRating, 5 stars1 month ago

really modern place, very clean. comfy beds, cool shower and good pool. Aircon really good and quiet. only negative was there could be more plates and utensils. would stay again.

4.89 out of 5 average rating, 9 reviews

Home in Tampa

Bring your family and friends to our luxury airbnb

AprilRating, 5 stars1 week ago

I was in town celebrating my 45th birthday with family, and this home was the perfect accommodation. We enjoyed the jacuzzi and pool the most! The home was clean, warm and inviting. Our host Leon was quickly responsive and extremely accommodating...he was able to grant us a last minute late check out, which we greatly appreciated. We'd definitely stay again if we ever find ourselves back in Tampa.