Vacation rentals with a pool in Holiday

Find and book unique homes with a pool on Airbnb

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Popular amenities for Holiday rentals with a pool

House rentals with a pool

Guest favorite

Home in Tampa

4.91 out of 5 average rating, 139 reviews

Pool Oasis | Karaoke | 5G | Theater 135" | Grill

TatianaRating, 5 stars3 days ago
Such a fun house! We loved the movie room, and pool the most. Very comfy beds, house was free of clutter. Definitely recommend!
Guest favorite

Home in Tampa

4.95 out of 5 average rating, 41 reviews

Upscale Tampa Dream Home Pool, Golf, Pool Table

JenniferRating, 5 stars5 days ago
Great place to stay, we had a wonderful time!
Superhost

Home in Spring Hill

4.65 out of 5 average rating, 71 reviews

Modern Pool Home Wi Fi Cable, Optional Pool Heat

AshleyRating, 5 stars6 months ago
wow ! beautiful, well maintained home ! the home was clean with lots of natural light. kitchen was well equipped with cooking Utensils. the pool was AMAZING 👏 back yard was full fenced making for lots of Privacy. strongly recommend. the rental agreement was basically the Exact same thing as the airbnb website so no need to be worried. affordable & well wroth it . Melinda was such a pleasure to work with . my family will be returning in sep for another week . plenty of family activities , groceries store and restaurants. located in a quiet and safe neighborhood. lots of towels and cleaning supplies. comfortable beds with lauge master. overall 5 stars.
Superhost

Home in Hudson

4.87 out of 5 average rating, 15 reviews

Hudson retreat, 3 Bedroom Pool Home!

CheriRating, 5 stars3 months ago
Did great communications regarding the hurricanes! The house was great
Guest favorite

Home in Seminole

4.92 out of 5 average rating, 108 reviews

4 bedroom and private pool, near to Clearwater

WhitneyRating, 5 starstoday
Maria was super responsive and answered any questions we had. The house was great and accommodating. The pool was cold as it’s not heated but was perfect to float in on the hot sunny days! Definitely would stay here again!
Guest favorite

Home in Largo

4.81 out of 5 average rating, 78 reviews

Tranquil Home. 2 minutes to Indian Rock Beach...

JamesRating, 5 stars2 months ago
This was a great home for our stay! We had a great time and will definitely reach out on our next trip!
Guest favorite

Home in Palm Harbor

5 out of 5 average rating, 32 reviews

Beautiful house with pool, fire pit, billiard room

DeirdreRating, 5 stars3 weeks ago
This home is beautiful, in a quiet neighborhood! The thoughtful owners have really gone the extra mile to include everything to make your stay fun for all ages, with lots of games for younger and older kids. The property inside and out is spotless and super organized to make everything easy for you! The best part is you can walk to local town centers with great restaurants, cafes, parks, bike and walking trails!
Guest favorite

Home in Seminole

5 out of 5 average rating, 23 reviews

Affordable luxe pool home near beaches

DianaRating, 5 stars1 month ago
Sue and Joe are amazing host. The pictures of the home are beautiful but its even better in person. Both Joe and Sue were very quick to respond to any questions that I had. The home had everything you could need for your vacation. My Family and I will definitely be back to their Airbnb in the future.

Condo rentals with a pool

Superhost

Condo in Indian Shores

4.9 out of 5 average rating, 20 reviews

POOL SIDE right on the BEACH 2 bdrm condo

CaseyRating, 5 stars1 month ago
This condo was perfect for our family vacation! We had everything we could have needed and our host made everything so easy.
Superhost

Condo in Tampa

4.93 out of 5 average rating, 76 reviews

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool

SandraRating, 5 stars2 weeks ago
We enjoyed our stay! The property was very clean and comfortable. Helena welcome us and wished us well and safe travels when we departed. We would definitely stay there again.
Guest favorite

Condo in Tampa

4.96 out of 5 average rating, 130 reviews

Tiki Themed Waterfront Condo on Tampa Bay

BeccaRating, 5 stars1 week ago
We stayed 1 night before boarding a cruise. Was exactly as described. Very cozy and very convenient to restaurants. Would highly recommend, close to port as well. Thanks for a very easy 1 night stay!
Guest favorite

Condo in St. Petersburg

4.91 out of 5 average rating, 22 reviews

Lovely 2 bedrooms condo with pool in Boca Ciega

EricaRating, 5 stars7 months ago
We had a great stay! The views were gorgeous from our balcony each evening and our host Matt was extremely responsive. He had great recommendations on pet-friendly beaches. Location was perfect to get between beaches and downtown St. Pete. We highly recommend this place, host and stay!
Guest favorite

Condo in Seminole

4.97 out of 5 average rating, 143 reviews

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶

HeatherRating, 5 stars2 weeks ago
Sandra’s place is lovely! Extremely clean, comfortable, and well stocked kitchen and toiletries. She really has thought of everything. It was helpful having ziploc bags and containers for packing food on the go, spices and pantry essentials, first aid kit for a bandaid that was needed, fans for the bedrooms, etc. I stayed here for a girls weekend and the three of us would all highly recommend it!
Superhost

Condo in Madeira Beach

4.81 out of 5 average rating, 129 reviews

Lovely Water View Condo, Top Floor, Steps to Beach

SharonRating, 5 stars6 days ago
From start to finish the experience with Kristin’s place was excellent. The location is fantastic, the unit was adorable with everything we needed, and Kristin was a great host. I highly recommend this property and host. Right now.
Guest favorite

Condo in Clearwater

4.93 out of 5 average rating, 143 reviews

5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.

MelissaRating, 5 stars1 month ago
David's place was absolutely amazing! We have never stayed in an AirBNB before, but the next one will definitely have big shoes to fill. David has everything you could want and more. The pictures matched exactly what we got. He had beach toys, beach towels, coolers. wagon, beach chairs. umbrella, and many other things. Kitchen had everything you would have at home. The only thing you will need to bring is clothes. Every time I contacted David before our vacation, he responded usually within a few hours. While we were there he answered almost immediately. I can't say enough good things about David's condo and him as an owner. Highly recommend! Watching the dolphins during breakfast was a plus! Thank you for everything David!
Guest favorite

Condo in Indian Shores

4.89 out of 5 average rating, 44 reviews

Intracoastal | Indian Shores | Beach across street

MarissaRating, 5 stars6 months ago
My husband and I loved staying here for our honeymoon. Very close to lots of local attractions like Jon’s pass and Indian rocks beach. For the fishing lovers, the location of being right on the intercostal was great for night fishing and there’s some nearby parks that having fishing piers as well. Really enjoyed the pool on site as well

Quick stats about vacation rentals with a pool in Holiday

  • Total rentals

    30 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Pasco County
  5. Holiday
  6. Rentals with pools