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Holiday Rentals in Pine Island

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Our top choices for Pine Island holiday rentals

9.8 out of 10, Exceptional, (137)
"Great, peaceful stay!! You could not ask for a better location!! "
United States
Allison Y.
The price is €421
includes taxes & fees
5 Jan - 6 Jan 2026
WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA
Charming RV with AC in Spring Hill - Perfect for a getaway

Camping in Brooksville

Cabin in the Olive Orchard
9.8 out of 10, Exceptional, (8)
"The hosts were wonderful and the property was exactly what I needed. Great place for R&R. First visit but definitely not my last! Highly recommended!!"
United States
Dana A.
The price is €125
includes taxes & fees
29 Dec - 30 Dec
Cabin in the Olive Orchard
9.6 out of 10, Exceptional, (14)
"Nice property. Close to everything we were wanting to do."
United States
Shelia H.
The price is €246
includes taxes & fees
4 Jan - 5 Jan 2026
Sweet retreat in the springs home near 19 on quiet, secluded half acre
10.0 out of 10, Exceptional, (1)
"So enjoyed our stay, lovely cottage had everything we needed. Loved the shower 🚿. Will definitely stay again "
United States
Corinn
The price is €210
includes taxes & fees
5 Jan - 6 Jan 2026
Garden Cottage Within Walking Distance to Downtown Brooksville
2.0 star property
8.8 out of 10, Excellent, (6)
"We had a good experience and would book it again if we’re in the area. "
United States
Dale
The price is €88
includes taxes & fees
29 Dec - 30 Dec
Pleasant Days Lodging Southwest Cottage

Holiday Home in Spring Hill

Weeki Wachee Pod
2.0 star property
10.0 out of 10, Exceptional, (20)
"Great place"
United States
John
The price is €199
includes taxes & fees
4 Jan - 5 Jan 2026
Weeki Wachee Pod
9.8 out of 10, Exceptional, (17)
"Pool is not heated, it was chilly. However the house was very clean other than I think bathrooms could have been cleaned better. Quiet neighborhood. Owner was wonderful and messaged back fast and let us check in a couple hours early which was wonderful. Over all great place to stay! "
United States
Nachole C.
The price is €229
includes taxes & fees
26 Jan - 27 Jan 2026
Entire home with Screened- In Pool , Fully Fenced.

Apartment in Spring Hill

Cozy little apartment in Sprin Hill!
9.8 out of 10, Exceptional, (21)
"We were very happy with our stay. Very clean and comfortable apartment."
United States
beth h.
The price is €154
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy little apartment in Sprin Hill!
9.8 out of 10, Exceptional, (16)
"The property was comfortable, clean, and very private. "
United States
Dave L.
The price is €194
includes taxes & fees
28 Dec - 29 Dec
Cabin #2 Zen At The Palms 5 Star Adult Resort minutes from scalloping & fishing
9.4 out of 10, Exceptional, (49)
"It was nice and clean. We had a great time "
United States
Marilyn P.
The price is €103
includes taxes & fees
1 Jan - 2 Jan 2026
Modern studio apartment with covered outside seating area
10.0 out of 10, Exceptional, (1)
The price is €173
includes taxes & fees
29 Dec - 30 Dec
Waterfront River Cabin | At Seven Sisters Springs
9.4 out of 10, Exceptional, (21)
"We loved staying in the Southwest Cottage at Pleasant days. The host was so accommodating are very nice. We loved feeding the horses and interacting with the dogs on site. We have already made reservations to stay again in August. We highly recommend staying here!!!"
United States
Deborah K.
The price is €93
includes taxes & fees
29 Dec - 30 Dec
Pleasant Days Lodging Southwest Cottage
9.8 out of 10, Exceptional, (6)
"Very clean and comfortable. Would stay there again. "
United States
Heidi S.
The price is €130
includes taxes & fees
28 Dec - 29 Dec
Welcome to our unique place where you can enjoy a quiet and pleasant atmosphere
9.8 out of 10, Exceptional, (9)
"It was a beautiful place and great stay"
United States
Braelynn S.
The price is €270
includes taxes & fees
2 Jan - 3 Jan 2026
Charming 2-bedroom bungalow in fabulous Homosassa with AC, WiFi
10.0 out of 10, Exceptional, (55)
"House was very clean and comfortable. Easy walk to several restaurants, boat ramp and quiet neighborhood."
United States
Audrey K.
The price is €315
includes taxes & fees
30 Dec - 31 Dec
Charming Waterfront Canal Home in beautiful Old Homosassa! 5 Kayaks, Dock, Bikes
9.2 out of 10, Wonderful, (31)
"Perfect cabin weekend getaway. "
United States
Lindsey G.
The price is €197
includes taxes & fees
1 Jan - 2 Jan 2026
A/C, Firepit, Grill, Pet Friendly
9.4 out of 10, Exceptional, (33)
"Very quiet place to stay"
United States
Luis
Cheerful 1 bedroom guest suite with pool and yard
8.8 out of 10, Excellent, (3)
"Had a great, comfortable stay at this full house. House was clean and well provisioned with comfy bed, couch, and great appliances in the kitchen. Host was communicative.and gave clear check in/out information. "
United States
Joseph B.
The price is €260
includes taxes & fees
3 Jan - 4 Jan 2026
2BR 2BA Family & Pet Friendly Retreat minutes from Weeki Wachee
10.0 out of 10, Exceptional, (3)
"Thanks so much for awesome stay!"
United States
Val K.
The price is €300
includes taxes & fees
7 Jan - 8 Jan 2026
Just a couple minute paddle to hospital hole in Weeki Wachee. Pet friendly.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pine Island Hotel Reviews

Find out more about Pine Island

Everything you need to know about Pine Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pine Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pine Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pine Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pine Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pine Island holiday rentals we have selected for you start as low as €270 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pine Island rentals

At Expedia, we put the best Pine Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pine Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pine Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pine Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Pine Island?

Yes, there are holiday rentals close to the most popular sights in Pine Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pine Island has to offer?

Waterfront w access to the Weeki Wachee River & Gulf of Mexico - Dog Friendly!: This holiday home rental outside of Pine Island is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Pine Island?

Choose from 8 Expedia holiday rentals in Pine Island for a memorable holiday.

What’s there to see and do in Pine Island?

While exploring the area, visit family-friendly sights like Adventure Coast Fun Park, or get outside and enjoy nature at Pine Island Beach Park. Bayport Park Boat Ramp and Weeki Wachee Springs State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Pine Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pine Island. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips.