An aerial view of a coastal town with residential areas, a baseball field, and a large body of water.

Pine Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Pine Island vacation rentals

1. WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA

WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA
Spring Hill
9.8 out of 10, Exceptional, (139 reviews)
"This stay—this home—was beyond wonderful! A beautiful, out-of-the-hubbub location mere steps from the beach. We took advantage of both decks and the beach daily, including frequent swimming in the Gulf. A very well-appointed kitchen, including a small, quiet dishwasher. Big TV with ample streaming services for after dark entertainment. Delicious food and atmosphere at Bayport Inn a couple miles away, but we dined in more often than not. What a blessing that this place is made available for...
United States
Dale H.
The price is CA $300
CA $707 total
includes taxes & fees
Oct 19 - Oct 20
WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA

2. The Funky Flamingo - Neptune's Grotto Old Florida Adventure Retreats

The Funky Flamingo - Neptune's Grotto Old Florida Adventure Retreats
Weeki Wachee
9.6 out of 10, Exceptional, (14 reviews)
"This was truly an incredible stay for me and my coworker for a getaway Girls day! Perfect location, cute as can be!"
United States
Sarah F.
The price is CA $89
CA $167 total
includes taxes & fees
Oct 18 - Oct 19
The Funky Flamingo - Neptune's Grotto Old Florida Adventure Retreats

3. Quiet getaway on a hidden Spring-run

Quiet getaway on a hidden Spring-run
Spring Hill
9.8 out of 10, Exceptional, (38 reviews)
"House was clean, fully equipped, and in a great location. We enjoyed our stay and would rent again!"
United States
Karey
The price is CA $325
CA $685 total
includes taxes & fees
Oct 18 - Oct 19
Quiet getaway on a hidden Spring-run

4. The Muddy Mermaid - Neptune's Grotto Old Florida Adventure Retreats

The Muddy Mermaid - Neptune's Grotto Old Florida Adventure Retreats
Weeki Wachee
9.6 out of 10, Exceptional, (8 reviews)
"Wife stayed 12 years ago and she awesome improvement we will definitely come back"
United States
chad c.
The price is CA $162
CA $272 total
includes taxes & fees
Oct 18 - Oct 19
The Muddy Mermaid - Neptune's Grotto Old Florida Adventure Retreats

5. Cozy Coastal style home with the river at your back door!

Cozy Coastal style home with the river at your back door!
Spring Hill
9.0 out of 10, Wonderful, (4 reviews)
"Loved it! I have stayed on the river more than a few times but never on this side (under the bridge past Roger’s park) but it was great! 5 min to Roger’s Park via my pedal Kayak. Home was clean and updated. Has so many kayaks available on-site including kids’ kayaks."
United States
ASHLEY D.
The price is CA $223
CA $566 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Coastal style home with the river at your back door!

6. Weeki Mermaid Retreat | Dock & River Adventures

Weeki Mermaid Retreat | Dock & River Adventures
Weeki Wachee
9.8 out of 10, Exceptional, (32 reviews)
"We had an absolutely amazing time. Location is perfect, house is perfect, service was excellent!!! Can’t wait to come back."
United States
Caitlin R.
The price is CA $294
CA $753 total
includes taxes & fees
Oct 18 - Oct 19
Weeki Mermaid Retreat | Dock & River Adventures

7. Little Bohemia!Springs/Gulf access! Kayaks & dock!

Little Bohemia!Springs/Gulf access! Kayaks & dock!
Spring Hill
10.0 out of 10, Exceptional, (3 reviews)
"Great little property well maintained and very clean. We loved our weekend stay here. The host was very gracious and worked with me to get early access to the dock prior to check in so I could get a full day out on the river. "
United States
Erin G.
The price is CA $154
CA $514 total
includes taxes & fees
Oct 18 - Oct 19
Little Bohemia!Springs/Gulf access! Kayaks & dock!

8. Bigfoot Bungalow -Enjoy being directly on clear waters of the Weeki Wachee River

Bigfoot Bungalow -Enjoy being directly on clear waters of the Weeki Wachee River
Weeki Wachee
10.0 out of 10, Exceptional, (34 reviews)
"Very nice home with excellent location."
United States
Theresa T.
The price is CA $308
CA $868 total
includes taxes & fees
Oct 19 - Oct 20
Bigfoot Bungalow -Enjoy being directly on clear waters of the Weeki Wachee River

9. Tiki Tropical Retreat - directly on the clear Weeki Wachee River (not a canal)

Tiki Tropical Retreat - directly on the clear Weeki Wachee River (not a canal)
Spring Hill
9.8 out of 10, Exceptional, (51 reviews)
"Always a wonderful time!!"
United States
Lori C.
The price is CA $285
CA $582 total
includes taxes & fees
Nov 3 - Nov 4
Tiki Tropical Retreat - directly on the clear Weeki Wachee River (not a canal)

10. Weeki Palace w/ Backyard Escape & River Access!

Weeki Palace w/ Backyard Escape & River Access!
Spring Hill
10.0 out of 10, Exceptional, (37 reviews)
"Amazing place to stay at! And great host!"
United States
mady a.
The price is CA $156
CA $419 total
includes taxes & fees
Oct 20 - Oct 21
Weeki Palace w/ Backyard Escape & River Access!

11. Entire home with Screened- In Pool , Fully Fenced.

Entire home with Screened- In Pool , Fully Fenced.
Berkeley Manor
9.8 out of 10, Exceptional, (44 reviews)
"amazing stay! It's a great place and has the perfect amenities to make a trip special."
United States
Martin B.
The price is CA $172
CA $440 total
includes taxes & fees
Oct 18 - Oct 19
Entire home with Screened- In Pool , Fully Fenced.

12. Waterfront Retreat + Kayaks - Extended Stay Deal

Waterfront Retreat + Kayaks - Extended Stay Deal
Spring Hill
9.6 out of 10, Exceptional, (16 reviews)
"Location of property was great"
United States
Virginia W.
The price is CA $359
CA $1,004 total
includes taxes & fees
Oct 19 - Oct 20
Waterfront Retreat + Kayaks - Extended Stay Deal

13. Weeki Wachee Pirate House

Weeki Wachee Pirate House
Spring Hill
9.8 out of 10, Exceptional, (9 reviews)
"This property was as described, clean, and perfect for a couples getaway. The kitchen had pretty much everything we needed. We were able to enjoy the provided kayaks and enjoyed our time here!"
United States
Alanea L.
The price is CA $273
CA $672 total
includes taxes & fees
Oct 19 - Oct 20
Weeki Wachee Pirate House

14. Fabulous waterfront home in Hernando Beach. Boat dock with direct gulf access.

Fabulous waterfront home in Hernando Beach. Boat dock with direct gulf access.
Hernando Beach
10.0 out of 10, Exceptional, (12 reviews)
"From the moment we arrived til we left this house had everything we needed and then some. Our kids loved the arcade games. Loved our stay there and loved that it was dog friendly with a fenced yard. The hosts were very friendly and answered any questions very quickly."
United States
Melissa C.
The price is CA $204
CA $523 total
includes taxes & fees
Oct 18 - Oct 19
Fabulous waterfront home in Hernando Beach. Boat dock with direct gulf access.

15. Stay directly on crystal clear waters of Weeki Wachee River with your own beach!

Stay directly on crystal clear waters of Weeki Wachee River with your own beach!
weekiwachee
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful home with everything we needed for a wonderful stay. Perfectly positioned on the spring with cozy beds and wonderful outdoor areas. "
United States
Christine C.
The price is CA $655
CA $1,180 total
includes taxes & fees
Nov 4 - Nov 5
Stay directly on crystal clear waters of Weeki Wachee River with your own beach!

16. Vintage Mermaid - Neptune's Grotto Old Florida Adventure Retreats

Vintage Mermaid - Neptune's Grotto Old Florida Adventure Retreats
Weeki Wachee
9.4 out of 10, Exceptional, (26 reviews)
"Loved our stay. Room and on site staff were great. Bed was amazing Will return!"
United States
Anonymous traveller
The price is CA $162
CA $272 total
includes taxes & fees
Oct 18 - Oct 19
Vintage Mermaid - Neptune's Grotto Old Florida Adventure Retreats

17. Sirenity - Neptune's Grotto Old Florida Adventure Retreats

Sirenity - Neptune's Grotto Old Florida Adventure Retreats
Weeki Wachee
9.2 out of 10, Wonderful, (12 reviews)
"Our stay was perfect for the quiet getaway we ere looking for. The place was clean and easy to find. The hosts were quick to communicate and help us have a comfortable stay!"
United States
Rebekah J.
The price is CA $177
CA $290 total
includes taxes & fees
Oct 18 - Oct 19
Sirenity - Neptune's Grotto Old Florida Adventure Retreats

18. Waterfront - Private Fishing & Boating Dock - 4 Kayaks - Gulf of America Access

Waterfront - Private Fishing & Boating Dock - 4 Kayaks - Gulf of America Access
Hernando Beach
9.8 out of 10, Exceptional, (31 reviews)
"We had an awesome trip - house was great and in a great area with lots to do. "
United States
kimmielou62
Waterfront - Private Fishing & Boating Dock - 4 Kayaks - Gulf of America Access

19. 3-bedroom Private Forest Retreat Home with Wifi and Full Kitchen

3-bedroom Private Forest Retreat Home with Wifi and Full Kitchen
Spring Hill
10.0 out of 10, Exceptional, (15 reviews)
"Quiet and great price"
United States
Tom P.
The price is CA $235
CA $329 total
includes taxes & fees
Oct 19 - Oct 20
3-bedroom Private Forest Retreat Home with Wifi and Full Kitchen

20. Cozy little apartment in Sprin Hill!

Cozy little apartment in Sprin Hill!
Spring Hill
9.8 out of 10, Exceptional, (27 reviews)
"The apartment was very clean and comfortable.nice modern finishes and a very nice, large shower. We would definitely stay again!"
United States
Sue B.
The price is CA $92
CA $249 total
includes taxes & fees
Oct 18 - Oct 19
Cozy little apartment in Sprin Hill!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pine Island Hotel Reviews

Find out more about Pine Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pine Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Pine Island?

Yes, we give you a choice of vacation rentals close to popular points of interest in Pine Island, or you can choose a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Pine Island has to offer?

Snorkel with the Manatees in Your Back Yard - Kayaks Included: This vacation home rental outside of Pine Island is located on the waterfront and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Pine Island?

Choose from 9 Expedia vacation rentals in Pine Island for a memorable vacation.

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 larger area.

What’s a vacation rental in Pine Island like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Pine Island. Vacation rentals offer extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.