Beach house vacation rentals in Longboat Key

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Popular amenities for Longboat Key beach house rentals

Beach house rentals with a pool

Top guest favorite
A cozy living area is presented with two sofas and an armchair, accented by decorative pillows. A wooden coffee table sits centrally, with plants strategically placed around the space. A television is mounted on the wall, displaying a scenic beach image. Natural light filters through multiple windows.
Home in Holmes Beach
5 out of 5 average rating, 18 reviews

Castaway Cottage

RayeRating, 5 stars2 weeks ago
The Castaway Cottage was exactly as described. Beautiful, clean and close to everything! Beds were comfy and sheets were so soft. The shower is AMAZING and of course the pool was a hit when you need a break from the beach. Amanda was quick to respond and her list of restaurants was very helpful and what we tried were all excellent. Everyone was friendly in the neighborhood and there were 2 parrots and an egret that would visit us by the pool often. Last, we rented their buggy for the week, it was charged and ready to go as soon as we arrived and hated to get back in a car. If you’re looking for a great place to stay look no further.
Superhost
A private heated pool is surrounded by tropical palms, featuring a gently curved shape with clear blue water. Two white adirondack chairs are positioned nearby on a paved patio, inviting relaxation in a tranquil outdoor setting.
Home in Anna Maria
5 out of 5 average rating, 3 reviews

The Shell House

JantzenRating, 5 stars1 week ago
Ammey & Ammey’s place was simply awesome. A hidden gem—calm & peaceful. Clean place with a great pool in a beautiful setting, steps from the sand. We loved having coffee in the screened in porch looking at the pool and beautiful landscape. Thank you, Ammey for sharing your place with us when we needed a break from the world. Would stay there over and over!
Guest favorite
Aerial view showcasing a luxury home nestled among lush greenery with water views. The surrounding landscape features a serene bay and nearby residences, emphasizing the privacy and tranquility of the location.
Home in Seminole
4.95 out of 5 average rating, 290 reviews

Waterfront Luxury Heated Pool/Hot Tub 5 bedrooms

SarahRating, 5 stars3 weeks ago
The house is beautiful and spacious. We had a large crew with us and never felt crammed. Our favorite spot was the table outside, under the house. The neighborhood is quiet, except for the dog across the way, but it was never a problem. The swamp smelled a little. The location is top notch - conveniently close to resturants and beaches. We recommend staying here if you have a large group who like their privacy!
Top guest favorite
A private pool is visible, featuring a heart-shaped design and surrounded by a smooth concrete patio. Sunlight reflects off the clear blue water. Lush greenery and a small garden border the area, with a barbeque grill positioned nearby. The house is partially shown in the background.
Home in Seminole
4.92 out of 5 average rating, 113 reviews

4 bedroom and private pool, near to Clearwater

AprilRating, 5 stars3 weeks ago
This was by far the best day we've had with Airbnb so far!! The house was so perfect for the price and the little amenities were so nice! They had yard games for kids to play and extra blow ups for the pool it was just such a lovely experience. The host was very responsive and understanding for adjustments that needed to be made or giving information I really enjoyed this stay!!
Top guest favorite
A sunlit swimming pool is surrounded by a screened enclosure, offering protection from insects. Chaise lounges are positioned alongside the pool, enhancing the relaxed atmosphere. Lush greenery is seen through the screen, creating a tranquil and inviting space for leisure.
Home in Largo
4.99 out of 5 average rating, 121 reviews

Modern Cozy 3BR | Walk to IRB Beach + Heated Pool

MarianaRating, 5 stars3 days ago
We had an amazing stay. The house was in a perfect location. The place was very clean and had all the necessities. It was close to the beach, restaurants, grocery stores and parks. The beach was beautiful and not crowded. Mikes Pizza and Pub and Kooky Coconut were great places to order from. My kids loved the pool and the nature park that was within walking distance. Beach toys, umbrellas and chairs were provided by the host. My family can’t wait to come back!
Top guest favorite
A vibrant backyard pool area features a shimmering blue in-ground pool, accompanied by colorful floaties. Glass doors provide a view into the interior living space, allowing natural light to enhance the inviting atmosphere. A spacious patio area is bordered by lush greenery.
Home in Seminole
4.96 out of 5 average rating, 123 reviews

Heated Pool luxury house, 4 mins from BEACH!

JeffRating, 5 stars2 weeks ago
Had a great stay at Anna’s place 4 mins from the beach ! We had a group of 4 . Everyone enjoyed the layout of the home. A little space for each of us . We enjoyed a few days out ( one day in Tampa) and one full day of “ pool time “ Thanks again , everyone really enjoy your home and the area was very convenient to bounce around for some nice day trips .
Guest favorite
A well-furnished living area features a light-colored sofa with decorative pillows, a glass coffee table, and an area rug with subtle patterns. A dark wooden entertainment unit holds a television, and natural light filters in through nearby windows, enhancing the serene ambiance.
Home in Largo
4.81 out of 5 average rating, 81 reviews

Tranquil Home. 2 minutes to Indian Rock Beach...

KathrinRating, 5 stars1 week ago
We spent 2 weeks in Gisele’s home…it was exactly as described. We really appreciated the outdoor space/patio. We enjoyed our morning coffee, utilizing the large bbq and outdoor dining area and ending our days with a nightcap in the enclosed patio. The location was great, centrally located with easy access to beaches from Clearwater to St. Pete’s. We will definitely return when back in the area again. Gisele is a great host.
Guest favorite
Home in Largo
4.92 out of 5 average rating, 125 reviews

Poolside Palms Private Pool & Game Room - 7 Min to Indian Rocks Beach

JanelRating, 5 stars6 days ago
This house was exactly what we needed. We had two families staying here with 4 kids. The bunk beds and play were was perfect for them. The pool was very clean and kept up

Family-friendly beach house rentals

Superhost
Home in Venice
4.77 out of 5 average rating, 133 reviews

South Venice, FL. Ideal vacation home.

KayRating, 5 stars1 month ago
We enjoyed Jan’s house. It was a quiet neighborhood, perfect for walking the dog. Short drive to restaurants, beaches, grocery stores, Shamrock Park, Brohard dog beach, pretty much anything we wanted to do. The lanai was a nice area to sit in the shade. Wish I had a way to post a recording of all the various birds chirping away! Home was clean and Jan was a responsive host with any questions we had. Yard was private and fenced in nicely for our dog. Appreciated having laundry soap, body wash, dish detergent, & paper goods to get through our stay. So often all you get is enough for a few days, if that. Comfortable beds too! We would stay again. Thanks Jan!
Top guest favorite
The exterior of the vacation home is showcased, featuring bright yellow doors framed by a welcoming pathway. Lush landscaping surrounds the entrance, while large windows allow natural light to fill the interior. A mixture of trees and shrubs adds to the greenery.
Home in Bradenton
4.76 out of 5 average rating, 175 reviews

Recently Updated! - Close to White Sandy Beaches!

EstherRating, 5 stars3 weeks ago
Aaron's house definitely served its purpose for our family vacation, loved the quiet neighborhood and local stores! The house could use some updates, like new bed sheets and a TV in the master bedroom, etc. Alomg with some outdoor updated landscaping (this coming from a landscaping professional 😊). Overall it was definitely worth it and we had a great experience, we loved AMI. Thanks Aaron!
Guest favorite
A wooden deck with steps leads toward a spacious outdoor area covered by a slatted roof, offering shaded seating arrangements. Lush landscaping frames the property, while expansive glass doors invite natural light into the interior space.
Home in Indian Rocks Beach
4.85 out of 5 average rating, 246 reviews

Amazing water front view home newly renovated

AnnRating, 5 stars2 weeks ago
We had a very enjoyable stay here. There were 5 of us and it was perfect, could have accommodated more. Master bath slightly small, though 2 sinks. Very spacious living area and deck is humongous, great view, and the greatest asset! Only drawback for us was that it was about a 15 min walk to beach - not insurmountable, but did mean we had to deal w/ a car every time we went bec we had “beach stuff” in tow.
Superhost
The open living area showcases a mix of light and neutral tones, featuring a spacious cream-colored sofa with an accompanying ottoman. A dining table with multiple chairs is positioned nearby, while large windows allow natural light to fill the space, highlighting the modern flooring.
Home in Madeira Beach
4.72 out of 5 average rating, 333 reviews

Beach Side STEPS TO BEACH!

KelliRating, 5 stars2 weeks ago
We had a wonderful stay! It was the perfect location, so close to the beach access and right across the street from John’s Pass. We felt right at home here and look forward to coming back again! Perfect spot for me, my husband, and 3 teenagers.
Guest favorite
Home in Sarasota
4.88 out of 5 average rating, 153 reviews

5 minutes to private Siesta Key Beach + 2 pools

NormRating, 5 stars1 month ago
Great place and location. Only 8 minute walk from the a nice beach. The place was cute, functional, and clean.
Guest favorite
A children's play area is organized with a colorful play mat on the floor, a red toy house, and a blue storage bin labeled 'TOYS.' Shelves contain various storage containers, and a laundry basket sits nearby, creating a child-friendly environment.
Home in St. Petersburg
4.91 out of 5 average rating, 108 reviews

Cozy Dream FL Vacation Home Pool is heated!

Walt And MicheleRating, 5 stars7 months ago
Very clean, great location to beach and my family. Walking area for our doggie and very close to shopping. We did pack too much. This home has everything you need. Nan is an awesome host.
Top guest favorite
A wooden desk with a blue desktop is positioned against a light-colored wall. A decorative yellow tree artwork hangs above it, complemented by a blue lamp and a bird figurine. A cozy gray armchair is placed beside the desk, with a tall, slender lamp nearby offering additional lighting.
Home in Tarpon Springs
4.96 out of 5 average rating, 360 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

HannahRating, 5 stars3 days ago
My family and extended family were extremely comfortable at Jeff’s place. There was everything we needed and more. It was convenient to have a pack and play plus a high chair. The kids loved collecting eggs everyday and swimming in the pool. Jeff was easy to communicate with and responded quickly with any questions we had. The location was perfect and not too far for day trips to the beach. We will definitely be returning in the future.
Guest favorite
Home in Clearwater Beach
4.97 out of 5 average rating, 223 reviews

Clearwater Beach Townhome w/Game Room & Boat Slip!

LeeRating, 5 stars4 days ago
Centrally located and spacious. Easy to walk to the beach and all of the restaurants in Clearwater

Beachfront house rentals

Top guest favorite
An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.
Home in Holmes Beach
5 out of 5 average rating, 25 reviews

FamilyTides~New! 30 sec walk to beach~Heated pool!

JayRating, 5 stars1 week ago
Our family had a wonderful stay. The home is exactly as described - beautifully decorated and has a perfect layout for a family of five to spread out and relax. Really appreciated the proximity to the beach (steps away) and the availability of the beach accessories and cart. Mark was super responsive when needed and I wouldn’t hesitate to book a future stay.
Guest favorite
Home in Indian Rocks Beach
4.77 out of 5 average rating, 47 reviews

3 Palms Retreat | Beachfront Retreat

AmyRating, 5 stars1 month ago
This property was amazing for our girls trip! So much space for everyone to have privacy, and the outside space is incredible beautiful and convenient! This place would be perfect for families to enjoy beach time together but also have privacy for down time. Amazing location with several restaurants in walking distance. You must visit the bakery - go early because they will Sell out if the beach is busy. The property is casual and inviting - not high luxury inside but updates and provides nice “Florida relaxed vibe”. We would absolutely Return to this property!
Superhost
A panoramic view of a sandy beach extends under a bright blue sky streaked with wispy clouds. Gentle waves lap at the shore, and a few figures can be seen walking along the water's edge. Sunlight highlights the fine, white sand.
Home in Sarasota
4.89 out of 5 average rating, 92 reviews

Renovated Beachhouse Private Beach Access, Unit S

PeytonRating, 5 stars9 months ago
Sheryl’s responsiveness and care for us was unmatched. We had an issue with the property that she resolved immediately and even called me personally to make sure my friends and I were taken care of. Great location and outstanding customer service.
Guest favorite
A bright and airy kitchen and dining area is featured, with a large wooden table surrounded by leather chairs. A central island offers additional preparation space. Light-colored cabinetry and modern appliances are visible, complemented by a decorative light fixture and a floral centerpiece.
Home in Indian Rocks Beach
4.9 out of 5 average rating, 135 reviews

Luxury 3 Bedroom Beach Home with Game Room!

IsabellaRating, 5 stars1 month ago
This place was even better than we could have expected. There was 8 of us staying here and we still felt we had more than enough space. The house is the perfect distance from the beach and cute restaurants/ areas to just walk around. The lower level was the perfect addition with the projector and different games that really made our trip. We spent a lot of our trip in the house due to the less than ideal weather but had no complaints because of how perfect and cute this spot was. The host was friendly and responsive which also made the experience nice. Overall would 100% recommend it, I would even stay here again!
Superhost
A spacious living and dining area is illuminated by natural light, featuring large windows. Comfortable seating includes a blue sofa and a patterned armchair. A wooden dining table is set with dishes, while decorative shelves display various items, enhancing the home's inviting design.
Home in Pass-a-Grille Beach
5 out of 5 average rating, 11 reviews

Beachfront- Quaint Beach front House Pass a Grille

NikiRating, 5 stars13 months ago
Katie was a great host - great communication before, during & after stay. Home was adorable and comfortable for family of 3. Beautiful sunset view from patio every night. Easy walking distance to restaurants and shops.
Guest favorite
A polished wooden staircase ascends towards a bright landing, designed with simple handrails. The hall features wooden doors and a plush rug, with natural light illuminating the space. A glimpse of the kitchen is visible through an open doorway, enhancing the inviting atmosphere.
Home in Indian Rocks Beach
4.88 out of 5 average rating, 8 reviews

Beautiful Home w/ Beach in the Backyard

SineadRating, 5 stars5 months ago
This place is absolutely beautiful. The home is full of character, wood floors, sash windows, it’s lovely. Plenty of room for a large family. And right on the beach. It’s amazing. We all loved our stay here & would highly recommend it.
Superhost
A cozy living area features two spacious sofas arranged around a low coffee table. Light hardwood floors enhance the bright atmosphere, complemented by natural light streaming in through large windows. The wooden ceiling adds warmth, while two pieces of wall art provide subtle decoration.
Home in Anna Maria
4.87 out of 5 average rating, 15 reviews

The Beach House 2 by Duncan Real Estate

BeckyRating, 5 stars7 months ago
This home was so perfect for our beach vacation, we especially liked the covered porch facing the beach with the big gum tree in front of it. All the amenities were provided, we had a grill to enjoy, so comfortable. We will definitely be back to enjoy it more!
Guest favorite
A cozy living area showcases a navy blue sectional sofa adorned with decorative pillows. Natural light streams through glass doors that open to a dockside view, while a dining table with woven placemats adds to the inviting ambiance.
Home in Madeira Beach
4.94 out of 5 average rating, 16 reviews

Water Front Boho 3BD/2BA House & 600 Feet to Beach

KayleeRating, 5 stars1 month ago
Very beautiful place to stay and in walking distance to John’s Pass. Host was very polite and responsive in messaging them. Would definitely visit again!

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