Pine Island Vacation Rentals

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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 $293
CA $688 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 $560
CA $878 total
includes taxes & fees
May 27 - May 28
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 $123
CA $371 total
includes taxes & fees
May 25 - May 26
Sweet retreat in the springs home near 19 on quiet, secluded half acre

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 $105
CA $278 total
includes taxes & fees
Jun 3 - Jun 4
Cozy RV Retreat with Private Hot Tub and Fenced Yard

Cabin in the Olive Orchard

Cabin in the Olive Orchard
Brooksville
10.0 out of 10, Exceptional, (11 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 $197 total
includes taxes & fees
May 25 - May 26
Cabin in the Olive Orchard

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 $65
CA $161 total
includes taxes & fees
May 25 - May 26
Modern studio apartment with covered outside seating area

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 $160 total
includes taxes & fees
May 24 - May 25
Pleasant Days Lodging Southwest Cottage

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 $156 total
includes taxes & fees
May 25 - May 26
NEW - Hippie Hut Minutes from the Boat Ramp

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 $101
CA $256 total
includes taxes & fees
May 26 - May 27
A/C, Firepit, Grill, Pet Friendly

Pleasant Days Lodging Southwest Cottage

Pleasant Days Lodging Southwest Cottage
Homosassa
9.4 out of 10, Exceptional, (23 reviews)
"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 CA $143
CA $169 total
includes taxes & fees
May 24 - May 25
Pleasant Days Lodging Southwest Cottage

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 $131
CA $308 total
includes taxes & fees
May 24 - May 25
Cabin #2 A Joyful Place 5 Star Adult Resort minutes from scalloping & fishing

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)
The price is CA $138
CA $348 total
includes taxes & fees
May 25 - May 26
Garden Cottage Within Walking Distance to Downtown Brooksville

Private Entry Cozy Suite w/ Ensuite Bath • Quiet • Parking • Long Stay Ready

Private Entry Cozy Suite w/ Ensuite Bath • Quiet • Parking • Long Stay Ready
Spring Hill
The price is CA $62
CA $112 total
includes taxes & fees
May 31 - Jun 1
Private Entry Cozy Suite w/ Ensuite Bath • Quiet • Parking • Long Stay Ready

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 $104
CA $262 total
includes taxes & fees
May 27 - May 28
Cheerful 1 bedroom guest suite with pool and yard

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 $205
CA $475 total
includes taxes & fees
May 29 - May 30
Entire home with Screened- In Pool , Fully Fenced.

Cabin #3 Zen At The Palms Private HOT TUB

Cabin #3 Zen At The Palms Private HOT TUB
Homosassa
10.0 out of 10, Exceptional, (8 reviews)
"Great communication, well located, and quiet. "
United States
Kaila S.
The price is CA $155
CA $356 total
includes taxes & fees
May 24 - May 25
Cabin #3 Zen At The Palms Private HOT TUB

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 $186 total
includes taxes & fees
May 24 - May 25
Relaxing Studio Just Minutes from Weeki Wachee Springs

3 Bed ~ 2 Bath~ Pool ~ Wifi ~ Pets Welcome ~Optional Heated Pool ~SS Barbecue

3 Bed ~ 2 Bath~ Pool ~ Wifi ~ Pets Welcome ~Optional Heated Pool ~SS Barbecue
Spring Hill
9.4 out of 10, Exceptional, (135 reviews)
"Very convenient stay for the snorkeling with the manatees. House was as described and very spacious. Had some minor issues with host that resulted in a confrontational phone call, however this resolved. "
United States
Ashley T.
The price is CA $155
CA $504 total
includes taxes & fees
May 31 - Jun 1
3 Bed ~ 2 Bath~ Pool ~ Wifi ~ Pets Welcome ~Optional Heated Pool ~SS Barbecue

South Brooksville, New Cozy Cottage, Convenient. 30 minutes from Tampa

South Brooksville, New Cozy Cottage, Convenient. 30 minutes from Tampa
Masaryktown
10.0 out of 10, Exceptional, (2 reviews)
"Pet friendly. Nicely decorated. Great bedding snd linens. Host has thought of everything with how the home is set up. "
United States
Dan N.
The price is CA $126
CA $229 total
includes taxes & fees
Jun 16 - Jun 17
South Brooksville, New Cozy Cottage, Convenient. 30 minutes from Tampa

Small but Cozy Private Stay/Weeki Wachee Springs

Small but Cozy Private Stay/Weeki Wachee Springs
Spring Hill
10.0 out of 10, Exceptional, (1 review)
"Great spot in an area that does not have alot of hotel options. Which was great as this little studio style space was far better than a hotel. Cutie little private patio to sit and have a glass of wine at the end of the day, as the patio faces east it is shaded from the hot FL sunshine in the evening. Well equipt little kitchenette with hot plate and all the necessities we needed to make and eat meals on site. "
United States
Jason
Small but Cozy Private Stay/Weeki Wachee 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.
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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.