Beach house holiday rentals in Pine Island

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Popular amenities for Pine Island beach house rentals

Beachfront house rentals

Guest favourite
Home in Spring Hill
5 out of 5 average rating, 46 reviews

Gulf-Front Oasis | Stunning Sunsets +Nature Views!

DawnRating, 5 stars1 month ago
Kelly's place was everything the listing promised and more. The location was peacefull and the views stunning! This is a great place to relax, enjoy nature, and spend time with family. We used the kayaks every day! We will definitely be back!
Top Guest favourite
Home in Spring Hill
4.94 out of 5 average rating, 47 reviews

Vay-cay Canalside at Sunshine & Splashes Cottage

HeatherRating, 5 stars1 week ago
We had a great weekend getaway! The river was gorgeous! Kayaks were a huge plus! We saw manatees right from the dock. Great location. Good restaurants close by. Enjoyed the coffee provided on the porch in the mornings. Very peaceful. Very clean. Would definitely stay again😊
Top Guest favourite
Home in Hernando Beach
4.93 out of 5 average rating, 30 reviews

*NEW* Waterfront - Private Dock, Hot Tub, 4 Kayaks

AllieRating, 5 stars9 months ago
We had a great anniversary trip at Brian's place! The house was well-appointed and had everything we needed. We enjoyed using the kayaks and the hot tub. We would definitely stay again!
Guest favourite
Home in Indian Rocks Beach
4.89 out of 5 average rating, 141 reviews

Luxury 3 Bedroom Beach Home with Game Room!

DeannaRating, 5 stars2 weeks ago
There were beach chairs, beach towels, wagon and toys. Also plenty of bathroom towels and the kitchen was well equipped. Our grandkids enjoyed the downstairs game room
Guest favourite
Home in Belleair Beach
4.95 out of 5 average rating, 207 reviews

Steps to a Private Beach Clearwater Belleair

KaylahRating, 5 stars1 day ago
The home was extremely clean and had everything we needed. It was the perfect size for 3 adults and a toddler. Walking distance from the beach made it even better! Susi and George were extremely responsive when we had questions and even made sure to send us local recommendations. Our first vacation with our toddler was extremely smooth with much help to them!
Guest favourite
Home in Hernando Beach
4.97 out of 5 average rating, 39 reviews

Waterfront Coastal Home w/ Private Pool & Dock

TonyRating, 5 stars5 months ago
We would stay here again. Spacious and clean with a super pool and lovely evening views watching dolphins from the upper deck. Angela responds quickly and is helpful. The house is very well stocked with kitchen and bathroom items. The location has local restaurants a 3 minute drive away. Great place to relax after Christmas!
Superhost
Home in Spring Hill
4.82 out of 5 average rating, 61 reviews

MainRiver-LG yard, 10Kayak, firepit,2 full kitchen

JenniferRating, 5 stars2 weeks ago
This home on the river is 10/10, amazing! This was our 3rd time staying here and we can’t wait to come back again! This spot on the river is the star of the show! We saw manatees and dolphins daily and my kids had a blast fishing for bluegill right off the seawall. The kayaks included are great! We recommend this house to everyone who’s looking for great place to enjoy the river!
Top Guest favourite
Home in Indian Rocks Beach
4.99 out of 5 average rating, 100 reviews

Dolphin Dreamer-6-Seat Golf Cart!

HenryRating, 5 stars1 month ago
I recently booked a trip with my girlfriend for my 25th birthday and was all in all IMPRESSED. I’ve been staying at places up and down the Gulf coast my whole life and have never had an experience like this before. Truly a hidden gem.

Beach house rentals with a pool

Top Guest favourite
Home in Hudson
5 out of 5 average rating, 66 reviews

FISH HAVEN-Gulf Home w/ Elev, Pool, Boat Ramp,Dock

CarolRating, 5 stars2 weeks ago
Hosts let us check in a couple hours early, as we hadn't had any sleep because of a death in the family. Diane met us at the house and showed us how to work the door locks, elevator, etc. The neighborhood is family-friendly and we felt safe there. I was able to walk some of the nearby streets. This home is at the end of a canal, which was nice for kayaking. It was easy access by car to Route 19, which gave us the ability to try a couple of locally owned restaurants, as well as accessing shopping centers. It's also an easy drive to/from Tampa International Airport, which is about an hour away, depending on traffic.
Guest favourite
Home in Palma Ceia
4.94 out of 5 average rating, 77 reviews

The Jungalow SOHO - Pool/Hot Tub

HeatherRating, 5 stars3 weeks ago
A private paradise! This was the best part of our family vacation. The house was immaculate and organized. The outside area was amazing. I loved enjoying morning coffee in the hot tub everyday and listening to all the birds. I will be back.
Guest favourite
Home in New Port Richey
5 out of 5 average rating, 8 reviews

Waterfront Oasis

KenRating, 5 stars1 month ago
Had the pleasure of staying here for a few days. Nice quiet neighborhood and a very peaceful and relaxing time hanging out here. Would not hesitate to book again only next time would like to book a fishing trip on the Reel Anomaly docked out back. Just book it and enjoy.
Guest favourite
Home in Hernando Beach
5 out of 5 average rating, 16 reviews

Boater's Paradise. No Hurricane Damage

JaneRating, 5 stars3 months ago
Scott's home is really an idyllic getaway - comfortable, clean, and lots of extras that you don't typically find in air B&Bs. Like bikes, kayaks, and a downstairs gym with ping pong, darts, foosball and air hockey! We really enjoyed our stay - loved relaxing by the pool, beds were comfortable, neighbors (and their pup Finley) were very friendly, and the location is a great spot to travel north or south to explore. We had a wonderful dinner at Brian's place. Only downside is that the beaches we tried to visit were closed, probably due to hurricane damage. Highly recommending staying with Scott - he's a very responsive host and his home is truly a gem!
Guest favourite
Home in Hudson
4.94 out of 5 average rating, 18 reviews

20% Off Florida Summer Vacation Rentals

HeatherRating, 5 stars6 months ago
We had a great time Thanksgiving week and thoroughly enjoyed the house and amenities.
Superhost
Home in Tarpon Springs
4.89 out of 5 average rating, 131 reviews

Game Room, Heated Pool, 5 minutes to Beach

MelissaRating, 5 stars3 weeks ago
good size house with a nice inground heated pool and 3 bathrooms. beds and pillows were comfortable. enough dishes and cookware to accommodate all of us. house is on a beautiful street, quiet mature neighborhood. only complaint was not having the arcade game available (that was to be a highlight for us) but we had ping pong and foosball. lg kitchen table and barstools for everybody to sit and comfortable couches. plenty of pool and beach toys in the garage for use!
Superhost
Home in Indian Rocks Beach
4.83 out of 5 average rating, 341 reviews

Stunning views! Spot dolphins from the pool!

LauraRating, 5 stars2 weeks ago
This home was everything we hoped for and more. The views with the pool overlooking the dock and water were absolutely breathtaking. We even spotted dolphins swimming by, which made the experience truly magical. The entire property was spotless, with beautiful fixtures and thoughtful touches throughout. From the layout to the amenities, everything was curated for comfort and ease. It felt like a private luxury retreat. We couldn’t have asked for a better stay and would return in a heartbeat!
Top Guest favourite
Home in Hernando Beach
5 out of 5 average rating, 17 reviews

3 BR Waterfront w/Heated Pool, kayaks and bikes!

JeniferRating, 5 stars1 month ago
A Jewel! This house was in a great location, very clean and had everything needed for a house for the week. My husband and I brought my Mom down for Mother's Day and her Birthday. We drove from Indiana to Florida to visit with my nieces and their family. We all had a great time with the pool and the house itself. Used the kayaks and paddle boards. The guys fished a few days off the pier and we saw a dolphin one evening in the area. I will have to say this is the first house where there was actually plenty of towels and pretty much a stocked kitchen. We will definitely stay again. Thank you!

Private beach house rentals

Superhost
Home in Hernando Beach
4.85 out of 5 average rating, 87 reviews

MarshaMellow a modern gulf retreat!

KathyRating, 5 stars3 weeks ago
Beautiful view and the gulf breeze on the porch was perfect any time of the day. Nice community. Close to restaurants and the boat ramp. Kitchen had everything we needed to cook our own meals. Very peaceful location, minutes from WeekiWachee.
Top Guest favourite
Home in Hudson
4.99 out of 5 average rating, 77 reviews

Angele's House, Waterfront with direct Gulf access

CarolRating, 5 stars2 weeks ago
This was the 2nd time we stayed at Angele's Place & we had a great time again! Its been redone since the hurricane & its even better than before! The house has everything you need to cook a meal, comfy beds & beach essentials! There's kayaks to use & the backyard & screened in lanai are great places to hang out! There's lots of good restaurants in the area & an ice cream shop within walking distance! Billy & Diane are great hosts & respond quickly to any questions! You won't be disappointed renting their place!
Top Guest favourite
Home in Hudson
4.97 out of 5 average rating, 33 reviews

Florida Keys escape in Hudson

PaulinaRating, 5 stars1 week ago
We absolutely loved your amazing home. The pictures don’t do this amazing place justice. The atmosphere was peaceful and serene. we had access to the kayaks. We were able to see the sunset while on the water we also saw manatees. Our stay was absolutely perfect! Thank you for making the check in and check out process flawless. Highly recommend and we will be back! Thank you again! :)
Superhost
Home in Hudson
4.83 out of 5 average rating, 48 reviews

SunWild Ventures Home *Golf Cart & Kayaks*

BlaineRating, 5 stars1 month ago
This place is very nice and cozy love that it’s on the water it’s beautiful and the golf cart is an amazing touch , the host is very nice and very accommodating
Top Guest favourite
Home in Hernando Beach
5 out of 5 average rating, 9 reviews

"It's a Shore Thing"

BridgetRating, 5 stars2 months ago
We had a wonderful stay at this home. It has a great open floor plan and they have everything you need for your stay. The screened in areas are also really nice to enjoy the view. Response time is fast and check in was so easy. We will definitely be back.
Top Guest favourite
Home in Hudson
5 out of 5 average rating, 18 reviews

Sunfish Adventures

YimmyRating, 5 stars3 weeks ago
Awesome spot! John had everything covered—coffee, bug spray, beach towels, even sunscreen. The house was super nice with cool decor and easy access to the Gulf. Would totally stay again!
Top Guest favourite
Home in Homosassa
5 out of 5 average rating, 11 reviews

Hellgate Island Scallop House (Boat access only)

TommyRating, 5 stars3 weeks ago
We had a great stay. It was very well stocked and comfortable. The owner even left some goodies that were a surprise. I had a few concerns about staying at a location only accessible by boat but it turned out great. It was a much needed relaxing getaway.
Top Guest favourite
Home in Hernando Beach
4.98 out of 5 average rating, 66 reviews

Beautiful 4 Bed/3 Bath, Direct Gulf Access Home

NidhiRating, 5 stars1 month ago
Had a blast with the family :)!!! Was everything as described and much more :)!!! Amaazing accommodating host!!! Can’t wait to come back, we simply loved it 🥰

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