Pine Island vacation rentals with pools

We found 5 vacation rentals waiting for you.

Find your ultimate splash pad

From plunge pools for a quick dip to infinity pools with a view, here are the Pine Island vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Pine Island rentals with pools

Our guests have spoken. Explore their favorite and top-rated homes in Pine Island with refreshing pools, sun-splashed decks, and poolside seating.

Coastal Escape
4 Bed | 3 Bath | Sleeps 10

Coastal Escape - Saint James City, FL

From $378
(excludes fees and taxes)
4.89 (9)
Bocilla Breeze
2 Bed | 3 Bath | Sleeps 9

Bocilla Breeze - Bokeelia, FL

From $337
(excludes fees and taxes)
4.81 (16)
Mermaid Haven at Bocilla
2 Bed | 2.5 Bath | Sleeps 6

Mermaid Haven at Bocilla - Bokeelia, FL

From $184
(excludes fees and taxes)
4.86 (14)
Bowline Oasis
3 Bed | 2 Bath | Sleeps 8

Bowline Oasis - Bokeelia, FL

From $311
(excludes fees and taxes)
4.25 (4)

Explore All Vacation Rentals With Pools

Recent guest reviews

We loved the location and spaciousness of this home. Furnishings were above average and the pool and spa area are great. Overall great experience.
Ian L. | Jul 2025
We very much enjoyed the quietness of the area in the quaint town at the lower end of the island. The house was lovely and has a nice layout; everything was so clean and organized. The inside of the house has been mostly updated and was done really well. There are some updates that still need to be done outside like new deck boards all around. Many of the boards are loose and have come undone from the fasteners and we had one board break creating a hole in the deck. You can tell the homeowners are working towards the updates as they had some landscaping done while we were there. Unfortunately these are the 2 reasons we are not giving it 5 stars; there was no notice of the major landscaping work going to happen for 3 of the days during our stay and the broken board didn’t get fixed until after we left. We reported it immediately to the management company when it happened and had to deal with it for several days. My sister and niece were able to enjoy having their own space by staying in the lower level with all the amenities you have on the main floor. The pool was amazing and we were able to enjoy playing in it day and night. We enjoyed fishing in the channel and got to watch manatees swimming by every day throughout the day! The island itself is amazing and the locals are great, friendly, and (unlike so many other places) they love having out of town visitors. We enjoyed lunch at the Waterfront Restaurant & Marina and drinks at Phuzzy’s. The guys at the local bait shop were very helpful and gave us hints on fishing the channels. Despite the heat we took advantage of a kayaking tour around the bridge connecting the island and mangrove trees which was only 10 mins away from the house. The nearest beach is almost an hour away along with most anything else you want to do. We knew this when we booked and already had the expectation but the reality hit while driving back to the house from the beach. Driving for an hour with salt on your skin is not ideal!
Kenneth K. | Jun 2025
We had a great time during our stay! We had several young kids and they were always entertained between the pool, the little sandy "beach," fishing, and going on our boats that we were able to take. Any time there was a question or concern the Vacasa team and the owner were very helpful and attentive.
Kara C. | Jun 2025
This is a beautiful house with everything needed for a great vacation. The location is perfect for boating.
Rachel Z. | Jun 2025
Best pricing

Book directly on Vacasa.com for the lowest rates.

3D virtual tours

Know exactly what you’re booking—no surprises.

Seamless check-in

Check in easily and quickly with a digital code.

Expert cleaning

Arrive to a spotless home with fresh linens.

FAQ

Our vacation rentals offer both private and shared pools. Each property’s listing description will specify whether the pool offered is private or shared.

Every home is stocked with plenty of towels. However, the availability of pool towels varies by property.

Some pools are heated, and there may be an additional fee for this service. You can find more information about heating fees in the property description.

Yes, pool maintenance is included during your stay. We ensure that pools and hot tubs are regularly cleaned and maintained to provide an optimal experience. If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately.

Many of our properties include lounge chairs, umbrellas, or shaded areas by the pool, but this can vary. Check the property details and listing photos for specific details.

Generally, food and drinks are allowed by—but not in—the pool. However, to be safe, it’s best not to use glass or china in the pool area.

Pool toys, floaties, or inflatables are typically not provided. You may want to bring your own, if needed.

Some properties include a poolside grill or outdoor kitchen area, but this is not standard across all rentals. Check the property listing for details.

We have a good neighbor policy that includes quiet hours from 10 p.m. to 8 a.m. In addition, certain communities have noise policies in place. Unauthorized parties are not allowed, and excessive noise can lead to intervention and removal from a property.

If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately. Your local Vacasa team will work to resolve the problem as quickly as possible.

Not all pools are open all year round. Some pools—depending on the destination—are seasonal only. Read the listing description for specific operating times for the pool.
USA > Florida > Pine Island > Pool