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Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples

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Exterior
Welcome to Dock Holiday! Bright scenic views from the living room and balcony.
Enjoy that first cup of coffee on your balcony overlooking the bay.
Full kitchens for making meals or heating leftovers.
Dock Holiday - relax in this comfy master bedroom.

Reviews

10 out of 10
Exceptional
4 bedrooms4 bathroomsSleeps 152400 sq ft

Popular amenities

  • Heated Pool
  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Outdoor grill

Explore the area

View in a map
Clearwater, FL
  • Place, Beach Walk
    ‪1 min walk‬
  • Place, St. Petersburg - Clearwater Beaches
    ‪3 min walk‬
  • Place, Pier 60 Park
    ‪9 min walk‬
  • Airport, Tampa, FL (TPA-Tampa Intl.)
    ‪42 min drive‬

Rooms & beds

4 bedrooms (sleeps 15)

Dock Holiday - Guest BR

2 Queen Beds

Dock Holiday - Master BR

1 King Bed

Dock of the Bay - Guest BR

1 Twin Bed and 1 King Bed

Dock of the Bay - Master BR

1 King Bed

Living Room 1

1 Double Sofa Bed

Living Room 2

1 Double Sofa Bed

4 bathrooms

Dock Holiday - Guest BA

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Dock Holiday - Master BA

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Dock of the Bay - Guest BA

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer

Dock of the Bay - Master BA

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Dining area

About this property

Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples

Double the space - Double the fun!
* 5-min walk to beach
* Stunning waterfront views
* 3 King suites + 1 2-Queen suite
* Sleeper sofas + twin bed
* No bunkbeds!
* Heated pool & sun deck
* Beach gear & wagons
* Free parking!

Your Clearwater Beach Getaway
Enjoy all the comforts of home—plus extras—in these beautiful side-by-side condos.

Sleep & Relax
• 4 private bedroom suites
• Split suites of privacy
• 2 comfy sleeper sofas
• 2 Pack & Plays
• TVs, large closets, dressers

Bathrooms
• Two with tub/shower combo
• Two with walk-in shower
• Blow dryer, magnifying mirror
• Toiletries in each bathroom

Kitchen & Dining
• Two fully equipped kitchens
• Stocked with dishes, pans, etc.
• Kid-size dishes + highchairs
• Keurig & drip coffee makers
• Cook in or enjoy take-out

Conveniences
• Hotel-style safes with passcodes
• 2 Full-size washer & dryers
• Free high-speed WiFi + internet
• Roku streaming + Cable TV
• Free on-site parking

Extras You’ll Love
• Beach wagons for trips to the sand
• Beach chairs, coolers, & umbrellas
• Pool & sundeck by the bay
• Professional cleaning

Good to Know
• Non-smoking property
• No pets allowed

Guests have full access to both condos, plus shared amenities to make your stay even more enjoyable:

* Bayfront pool & sundeck
* Picnic area & grill
* Dock for relaxing & fishing!
* Peaceful areas to unwind
* Free on-site parking included

Location, location, location! We are within easy walking distance of most everything. Forget the rental car -- walk to wherever you want to go! There are also several places to rent bikes or golf carts. Two parking permits are provided for free parking in the parking lot. (Let us know if you'll need up to four free parking spots.)

Need only one condo?
You can rent each condo separately. Search for Dock Holiday or Dock of the Bay in Clearwater Beach.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
Take out the trash
Turn off the lights
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Clearwater Beach

Located in Clearwater Beach, this condo is on the waterfront. The area's natural beauty can be seen at St. Petersburg - Clearwater Beaches and Pier 60 Park. Looking to enjoy an event or a game while in town? See what's going on at Jack Russell Stadium, or consider a night out at The BayCare Sound. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking and cycling.
Map
Clearwater, FL

What's nearby

  • Beach Walk - 1 min walk - 0.2 km
  • St. Petersburg - Clearwater Beaches - 3 min walk - 0.3 km
  • Captain Blighs Landing - 6 min walk - 0.6 km
  • Pier 60 Park - 9 min walk - 0.8 km
  • Clearwater Beach - 17 min walk - 1.5 km

Getting around

  • St. Petersburg-Clearwater Intl. Airport (PIE) - 20 min drive

Restaurants

  • ‪Shephard's Beach Resort - ‬4 min walk
  • ‪Badfins Food + Brew - ‬8 min walk
  • ‪Frenchy's South Beach Cafe - ‬5 min walk
  • ‪Coco's Crush Bar & Grill - ‬5 min walk
  • ‪Crabby Bar & Grill - ‬5 min walk

Frequently asked questions

Does Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples?

As of Apr 15, 2026, prices found for a 1-night stay for 2 adults at Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples on Jun 2, 2026 start from $878, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples?

Check-in begins at 4:00 PM.

What time is check-out at Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples?

Check-out is at 11:00 AM.

Where is Two Side-by-Side Waterfront Condos! Perfect for 2 families or 4 couples located?

Situated on the waterfront, this condo building is within a 5-minute walk of Beach Walk and St. Petersburg - Clearwater Beaches. Pier 60 Park and Clearwater Beach are also within 1 mi (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 27 out of 27 reviews
Rating 8 - Good. 0 out of 27 reviews
Rating 6 - Okay. 0 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Susan I.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and very beautifully decorated. Host is great and everything is supplied that you need for a wonderful vacation. Would stay there again for sure.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Patti M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location! Condos were perfect and had everything needed while on vacation.

Renting from hosts was easy and very responsive.
Stayed 7 nights in May 2023
Verified

10/10 Excellent

Karen T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Florida Road Trip

EVERYTHING was absolutely amazing and fantastic from location, very clean/neat condo and wonderful hosts!!! We couldn't have been more satisfied with our stay and absolutely can't wait to return!!!
Stayed 14 nights in May 2025
Verified

10/10 Excellent

Wendy G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Place!

This location was a short notice stay and it was clean, accommodating and the hosts were absolutely the best at being responsive and answering any questions we had. Would highly suggest booking this place if you need to be in the area!
Stayed 15 nights in Oct 2024
Verified

10/10 Excellent

Sarah S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Time with family

The properties were clean, beautiful and in a perfect short walking location to the beach. The properties had everything we needed for the week, making it a perfect place to stay with our families that came in by plane. The owners were extremely responsive and helpful in anything we needed. We would be happy to stay there again!!
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Ronnie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time at the Dockside Duo! Kit helped us every step of the way!Lovely well equipped condos, generous welcome basket and a beautiful view of the marina.We couldnt have asked for more.Thank you Kit and Gary!
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Jan K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property

Dockside Duo condos were everything that was advertised and more. Very clean, beautifully decorated and great location. So many things to do and within walking distance to so many great restaurants and shops and most importantly to the beach. We loved our stay and will be back again.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Donna B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beach week

Really enjoyed our stay! Kit was wonderful! Perfect location and very nice accommodations. Our family was visiting for a wedding and the dockside duo was a great layout! Only drawback was pool under repairs. Luckily beach is very close! Really enjoyed our stay!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Daniel D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Time

We had a large group and the accommodations were perfect!! Awesome family time!! Would highly recommend.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Pam G.

Liked: Cleanliness, check-in, communication, listing accuracy

Sibling Vacation

Very nice condos. Well stocked. Hosts were very responsive to requests. Loved the decor. Only real complaint were the beds were very high.
Stayed 5 nights in Apr 2024
Verified

10/10 Excellent

Melissa B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very Nice!

These owners are the best I have ever dealt with. Very thorough, very clean and respond right away to any questions.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Cheryl S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Dockside Condo

These beautifully decorated beachy condos were perfect for our family reunion, accommodating ages from 1 to 87 yrs. The 2nd floor condos were walking distance to the beach and restaurants! The kitchen was stocked with everything we needed to cook and both condos had beach items so we could enjoy the beach! The owners were very responsive and left a welcome basket for us upon arrival!
Stayed 7 nights in Dec 2022
Verified

10/10 Excellent

Leslie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great condos!

The condos were both very clean and nicely decorated. The entire property was well maintained, including al of the common areas. Parking was very easy, despite us visiting over a holiday weekend. Both units were very well stocked with linens and beach items. Only a short 5 minute walk to the beach. Owners were very communicative throughout the entire process. Would definitely book again!
Stayed 7 nights in May 2024
Verified

10/10 Excellent

Kristi D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property!

Kit & Gary were very responsive! We even had a couple of unforeseen issues and they were quick to get them handled and taken care of. The home is lovely and location is great! Just a short walk to beautiful Clearwater Beach and restaurants. We had an amazing trip and can’t wait to visit again next year! Thank you for sharing your beautiful home with our family.
Stayed 5 nights in Jun 2020
Verified

10/10 Excellent

Debbie T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome rental!!

We stayed at Dock-side Duo for family vacation. Having both units was amazing. We split 2 adults and 1 kids in each unit. Great location for walking to the beach and restaurants. The unit was as described. Very clean and well equipped. Beach chairs, umbrellas, cooler and beach towels all provided. One of the best VRBO rentals we have stayed in. Owners quick to respond.
Stayed 7 nights in Jun 2022
Verified

10/10 Excellent

Jamie F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Trip

The dockside duo was the perfect space for our family of 7. Having the 2 condos back to back was so convenient. Perfect walking distance to pier 60 and Beach Walk. Traveling with 2 toddlers it was great to have high chairs and pack and plays available. Plus all the beach supplies available at our fingertips. Kit kept communication open and was accommodating allowing us to check in a couple hours early the day of our arrival. This was our first time booking through VRBO and I couldn’t be more pleased with our choice.
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

Monica W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

After Christmas Getaway

We rented the side by side condos for our group of 11. The condos were just as the pictures described. Everything was very clean and we had a few supplies to hold us over until we got our groceries. The welcome basket was so thoughtful. It had snacks and wine. The owners were very easy to reach and super responsive if we had a question. The place is in the perfect location to walk to the beach or walk around the beach area. We walked everywhere and it was so easy to get to the beach with the wagons and chairs that were provided. We were all thoroughly impressed and had such a great time. We are hoping to book for next year as well.
Stayed 7 nights in Dec 2023
Verified

10/10 Excellent

Diane L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

Dockside Duo was such a good find for us! We were all able to be together (5 adults, 2 children) but still give our daughter and her family their own space for the kids’ naps/bedtime. We were close enough to the attractions and shopping areas but not in the thick of the traffic and noise in the area. The walk to the beach was easy, and the owners provided chairs, towels, a small cooler and even a “sand wagon” to transport it in. Having a swimming pool on property as an option for a quick cooling off was an added bonus. Looking out over the water in the mornings and evenings was such a pleasure for all of us too. Can’t say enough about the owner’s responsiveness and attention to detail throughout both units. We would absolutely plan a stay here again.
Stayed 7 nights in Apr 2024
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Merveilleux !

Grands condos, plein de commodités, vue magnifique, emplacement parfait! La plage est incroyable!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Nathan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property and hosts

We are used to staying in a hotel when coming to town for our conference each year. We will be staying here from now on. The Dock duo was all that it was advertised to be. Excellent location, very clean, great hosts. Highly recommend if you are traveling with family, friends or for work.
Stayed 6 nights in Nov 2022
Verified

10/10 Excellent

Anna D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property and very clean!

Beautiful property and was very well equipped in the kitchen, bedrooms, bathroom and living space. Very spacious rooms and very nice people to deal with which made my stay a stress free holiday. Thank you so much I highly recommend this condo at dock side with a beautiful view of the bay and a large balcony!!! I can’t say one bad thing about this place!
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

Jill C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

We had a great stay at this property. Everything was very clean and as advertised.
Stayed 7 nights in Apr 2022
Verified

10/10 Excellent

krista f.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very clean

We rented both units for our family vacation of 8. The condos were VERY clean and had everything you could want/need for your stay! The location was just a couple of min walk to beach, and was located in a quieter area of Clearwater. It was walking distance to shops and restaurants. Very satisfied with our stay, and would recommend!!
Stayed 6 nights in Oct 2021
Verified

10/10 Excellent

Dottie J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

This location was top of the line!

The condo was wonderful! It was so modern and clean! They had everything available for us that we could ever think of needing on our trip. The access to the beach, shops and restaurants was with in 2 minutes. The balcony over looking the bay was gorgeous and we saw dolphins daily! My son caught 56 fish off of the dock! We would absolutely rent this property again , we were thoroughly impressed with the communication from the owner and the overall experience!
Verified

10/10 Excellent

Mary H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful condo in Clearwater Beach

We rented the side by side condos, Dock Holiday and Dock of the Bay, for a week with 3 other couples, they were exactly as pictured and very clean. The location is perfect, easy walk to beaches and restaurants. I can't say enough about how accommodating and helpful the owners were. I would highly recommend these condos for a vacation in Clearwater Beach.
Stayed 7 nights in May 2021

About the host

Hosted by Kit & Gary Elert

Host profile image
Gary and I are from the Midwest and knew that once our kids were off to college that we wanted to live someplace warm during the winter months! We had visited Clearwater Beach several times over the years, so chose to rent a condo for a month back in 2012. We liked it so much, we rented for three months the next year and five months the following year. At that point, we knew that Clearwater Beach was where we wanted to stay, so we bought a house on North Clearwater Beach and now live there eight months of the year.

Why they chose this property

In 2017, we decided to invest in a condo that we could use when family and friends came to visit, plus rent out to guests looking for a great beach vacation and/or to check out Clearwater Beach for a potential winter vacation spot, just like we did years ago. We looked at several buildings, but selected Dockside Condominiums because of its superb proximity to the beach, shops, restaurants, marina, and other local attractions. Since our first condo was so popular, we decided to invest in a second condo in 2019. We purposefully purchased the condo directly next to our existing condo to accommodate multiple families traveling together. Families can maintain privacy by being in two separate condos, but enjoy the benefits of being side-by-side for easy planning and adventures! You can walk anywhere and you will hardly need a car except to explore areas off the beach. Though we're in the heart of the Beach, our condos face the Bay so you rarely hear the nightlife once you turn in for the night.

What makes this property unique

The balconies, patio, pool, sundeck, and docks all overlook the bay. You'll see gorgeous sunrises and dolphins playing right from your dining room windows!

Languages:

English

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