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

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, (141 reviews)
"We loved our break at Springtide. Perfect location in the lovely village of St Merryn. The accommodation is very well equipped, clean and comfortable. We can’t wait to book again"
United States
leah c.
The price is CA $291
CA $684 total
includes taxes & fees
May 25 - May 26
WELCOME TO A PARADISE GETAWAY IN WEEKI WACHEE FLORIDA

Beach front!!! Step off the last stair and into the Gulf!!!

Beach front!!! Step off the last stair and into the Gulf!!!
Spring Hill
The price is CA $558
CA $875 total
includes taxes & fees
May 29 - May 30
Beach front!!! Step off the last stair and into the Gulf!!!

Sweet retreat in the springs home near 19 on quiet, secluded half acre

Sweet retreat in the springs home near 19 on quiet, secluded half acre
Homosassa
9.8 out of 10, Exceptional, (16 reviews)
"Host was super sweet, beds were very comfy, and we had everything we needed! Would definitely stay again."
United States
Anonymous traveller
The price is CA $122
CA $369 total
includes taxes & fees
May 26 - May 27
Sweet retreat in the springs home near 19 on quiet, secluded half acre

Cabin in the Olive Orchard

Cabin in the Olive Orchard
Brooksville
9.8 out of 10, Exceptional, (10 reviews)
"Great gateaway! Beautiful place and love that we could sleep in a comfortable bed while looking at the stars! "
United States
Delphine R.
The price is CA $76
CA $196 total
includes taxes & fees
Jun 9 - Jun 10
Cabin in the Olive Orchard

Cozy RV Retreat with Private Hot Tub and Fenced Yard

Cozy RV Retreat with Private Hot Tub and Fenced Yard
Spring Hill
10.0 out of 10, Exceptional, (1 review)
"Property very private and I recommend the stay there very highly."
United States
Raul Rivera
The price is CA $102
CA $274 total
includes taxes & fees
Jun 2 - Jun 3
Cozy RV Retreat with Private Hot Tub and Fenced Yard

Pleasant Days Lodging Southwest Cottage

Pleasant Days Lodging Southwest Cottage
2.0 star property
Homosassa
8.8 out of 10, Excellent, (10 reviews)
"We had a good experience and would book it again if we’re in the area. "
United States
Dale
The price is CA $128
CA $159 total
includes taxes & fees
Jun 17 - Jun 18
Pleasant Days Lodging Southwest Cottage

Cheerful 1 bedroom guest suite with pool and yard

Cheerful 1 bedroom guest suite with pool and yard
Spring Hill
9.4 out of 10, Exceptional, (38 reviews)
"The place was clean and comfortable. It was quiet and the pool was lovely. I highly recommend."
United States
RebeccaL
The price is CA $103
CA $257 total
includes taxes & fees
Jun 16 - Jun 17
Cheerful 1 bedroom guest suite with pool and yard

Cabin #2 A Joyful Place 5 Star Adult Resort minutes from scalloping & fishing

Cabin #2 A Joyful Place 5 Star Adult Resort minutes from scalloping & fishing
Homosassa
9.6 out of 10, Exceptional, (20 reviews)
"Cabin was super cozy, and it’s a beautiful spot. "
United States
Dallas R.
The price is CA $130
CA $307 total
includes taxes & fees
May 30 - May 31
Cabin #2 A Joyful Place 5 Star Adult Resort minutes from scalloping & fishing

Waterfall Suite at Zen at the Palms with a Private Hot Tub by the Waterfall!

Waterfall Suite at Zen at the Palms with a Private Hot Tub by the Waterfall!
Homosassa
9.6 out of 10, Exceptional, (12 reviews)
"Absolutely amazing, definitely coming back."
United States
Thomas H.
The price is CA $199
CA $395 total
includes taxes & fees
May 23 - May 24
Waterfall Suite at Zen at the Palms with a Private Hot Tub by the Waterfall!

Modern studio apartment with covered outside seating area

Modern studio apartment with covered outside seating area
Spring Hill
9.4 out of 10, Exceptional, (58 reviews)
"The people were great and the place was quiet. The place was very clean and comfortable. Would recommend the place."
United States
Gloria S.
The price is CA $64
CA $161 total
includes taxes & fees
May 23 - May 24
Modern studio apartment with covered outside seating area

Garden Cottage Within Walking Distance to Downtown Brooksville

Garden Cottage Within Walking Distance to Downtown Brooksville
Brooksville
10.0 out of 10, Exceptional, (7 reviews)
"So enjoyed our stay, lovely cottage had everything we needed. Loved the shower 🚿. Will definitely stay again "
United States
Corinn
The price is CA $137
CA $346 total
includes taxes & fees
May 25 - May 26
Garden Cottage Within Walking Distance to Downtown Brooksville

Relaxing Studio Just Minutes from Weeki Wachee Springs

Relaxing Studio Just Minutes from Weeki Wachee Springs
Spring Hill
10.0 out of 10, Exceptional, (4 reviews)
"Super cute and close to everything!"
United States
Laura
The price is CA $93
CA $185 total
includes taxes & fees
May 24 - May 25
Relaxing Studio Just Minutes from Weeki Wachee Springs

Warm and cozy home in quiet neighborhood!! LLC

Warm and cozy home in quiet neighborhood!! LLC
Spring Hill
9.6 out of 10, Exceptional, (29 reviews)
"Welcoming host, nice house, Xmas decorations were a bonus. Has everything you need. "
United States
Paul C.
The price is CA $109
CA $449 total
includes taxes & fees
Jun 2 - Jun 3
Warm and cozy home in quiet neighborhood!! LLC

Entire home with Screened- In Pool , Fully Fenced.

Entire home with Screened- In Pool , Fully Fenced.
Berkeley Manor
9.8 out of 10, Exceptional, (24 reviews)
"The host was wonderful and house clean and welcoming "
United States
Kelly F.
The price is CA $204
CA $473 total
includes taxes & fees
May 29 - May 30
Entire home with Screened- In Pool , Fully Fenced.

Backyard Oasis with Pool • 10 min to Weeki Wachee

Backyard Oasis with Pool • 10 min to Weeki Wachee
Spring Hill
9.0 out of 10, Wonderful, (4 reviews)
"Just what we needed for attending a wedding in the area conveniently located to so much"
United States
Corina
The price is CA $149
CA $396 total
includes taxes & fees
Jun 2 - Jun 3
Backyard Oasis with Pool • 10 min to Weeki Wachee

Charming 1-bedroom apartment with WiFi, AC in marvelous Spring Hill

Charming 1-bedroom apartment with WiFi, AC in marvelous Spring Hill
Spring Hill
10.0 out of 10, Exceptional, (12 reviews)
"Lovely place in a quiet neighborhood. Close to amenities and attractions. Host was very nice and quick to respond when messaged. "
United States
Joel G.
The price is CA $83
CA $243 total
includes taxes & fees
May 23 - May 24
Charming 1-bedroom apartment with WiFi, AC in marvelous Spring Hill

NEW - Hippie Hut Minutes from the Boat Ramp

NEW - Hippie Hut Minutes from the Boat Ramp
Homosassa
9.0 out of 10, Wonderful, (39 reviews)
"Great place, very clean"
United States
Sean
The price is CA $81
CA $155 total
includes taxes & fees
May 30 - May 31
NEW - Hippie Hut Minutes from the Boat Ramp

Charming 2-bedroom house in peaceful Old Homosassa

Charming 2-bedroom house in peaceful Old Homosassa
Homosassa
10.0 out of 10, Exceptional, (18 reviews)
"The house is super cute and was perfect for our needs. The location was great. The rooms were incredibly clean and we really appreciated the snacks!"
United States
Erin
The price is CA $214
CA $312 total
includes taxes & fees
May 26 - May 27
Charming 2-bedroom house in peaceful Old Homosassa

A/C, Firepit, Grill, Pet Friendly

A/C, Firepit, Grill, Pet Friendly
Homosassa
9.4 out of 10, Exceptional, (36 reviews)
"Quiet private location"
United States
Andrew C.
The price is CA $100
CA $255 total
includes taxes & fees
May 26 - May 27
A/C, Firepit, Grill, Pet Friendly

Cozy River Cabin | Escape to Seven Sisters Springs

Cozy River Cabin | Escape to Seven Sisters Springs
Homosassa
9.4 out of 10, Exceptional, (13 reviews)
"Location was good."
United States
Amanda A.
The price is CA $135
CA $296 total
includes taxes & fees
Jun 7 - Jun 8
Cozy River Cabin | Escape to Seven Sisters Springs
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?

Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping: This vacation home rental outside of Pine Island is located on a river and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Pine Island?

Choose from 10 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.