Beachfront vacation rentals in Siesta Key

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Popular amenities for Siesta Key beachfront rentals

Beachfront home rentals with a pool

Guest favorite
The open-concept kitchen and dining area feature modern furnishings, with a spacious table for six and bar seating along the kitchen island. Floor-to-ceiling windows provide unobstructed views of the beach, allowing natural light to brighten the room.
Condo in Sarasota
5 out of 5 average rating, 6 reviews

Stunning Siesta Vistas Direct Beach Access & Pool

AlexRating, 5 stars21 months ago
I rented this place for my parents. They like it so much. The host is very responsible. I highly recommend this place
Guest favorite
A heated swimming pool is surrounded by a paved deck, furnished with blue lounge chairs and umbrellas. Lush greenery is visible in the background, and a clear blue sky stretches overhead, enhancing the open atmosphere of the area.
Home in Siesta Key
4.77 out of 5 average rating, 512 reviews

Beachfront Getaway in Siesta Key

AdairRating, 5 stars5 days ago
Our stay was so easy and enjoyable! Dior’s place is so cute and very clean. We were able to walk to multiple shops, bars, and restaurants. It was so nice to have our private beach access right down the sidewalk, and right beside the pool! We were also so glad that she was able to accommodate us on such short notice. Everything was perfect! This will definitely be our go-to place to stay when we visit Siesta!
Guest favorite
A clear view of a tranquil pool area framed by neatly arranged lounge chairs, providing ample relaxation space. Umbrellas offer shade beside a glistening pool, surrounded by palm trees and well-maintained grounds. The building's architecture features a modern design with vibrant red accents.
Condo in Siesta Key
4.94 out of 5 average rating, 96 reviews

The Honeymoon Suite on Siesta Key Beach

AshleyRating, 5 stars4 weeks ago
This was our first time to Siesta Key so we weren’t disappointed. . We didn’t get into late and in the dark the place was a little harder to find. The pool is a good landmark. Eric had the home feeling welcoming upon arrival. There was complimentary champagne, red wine, cold waters, and candies. Plenty of towels including a few for pool and beach. Was nice to sit out on the patio in the morning and enjoy the sunshine and some coffee. It was about a mile walk down to the Village where most of the shopping, restaurants, coffee shops, and things to do were, but it was an easy walk and/or short trolley ride to get there. Overall, we enjoyed our stay.
Guest favorite
Home in Siesta Key
5 out of 5 average rating, 30 reviews

Paradise In Siesta!

VanessaRating, 5 stars1 month ago
Paradise in Siesta was the perfect property for our vacation! The house is exactly as it is pictured, has everything that we needed, plenty of space, great decor and comfortable beds. It’s a great neighborhood with a private little oasis in the backyard, a great pool with lots of pool toys and there’s also a bathroom right off the pool area which is very convenient so you don’t have to walk through the house all wet. I hyped up the bunk beds to my kids before the trip but didn’t realize that the top bunks don’t have sides so we had an adult in the top bunk instead and she said it was still very comfortable and plenty of room so no big deal! We would absolutely stay here again! And would highly recommend this house to others.
Guest favorite
A bright lanai area showcases large glass sliding doors, providing views of the ocean and surrounding palm trees. Two light-colored armchairs and a wooden coffee table are arranged for relaxation, allowing for a comfortable space to enjoy the breeze.
Condo in Siesta Key
5 out of 5 average rating, 39 reviews

Amazing beach view! Entire unit renovated!

RhondaRating, 5 stars1 week ago
Such a beautiful place to stay! Very clean! The kitchen was stocked with all the dishes you will need. The view was amazing!!! The free trolly into the village was so easy. The beach accessories were so nice to use. All we had to do was cross the street and we were on the beach. The pool area was also very nice! Grilling area was nice and clean and a small smoking area so my husband could enjoy a few cigars. Great communication! Thank you! Was a fantastic vacation!
Top guest favorite
A dining area is visible with a wooden table surrounded by blue upholstered chairs. Large windows offer views of the beach and turquoise waters, providing a bright, airy atmosphere enhanced by natural light. Coastal-themed artwork adorns the wall, complementing the serene beach scenery.
Condo in Sarasota
5 out of 5 average rating, 43 reviews

Breathtaking Beachfront Views in Siesta Key

MattRating, 5 stars1 month ago
Really can’t beat the location and access to club-only beach area. No public beach was a huge benefit. The condo was great and owners were incredible! We truly enjoyed our family stay!
Top guest favorite
A light-filled living area features a comfortable white sofa and a blue accent chair. A wooden coffee table is centered on a textured rug. Large sliding glass doors offer views of the ocean and outdoor seating, framed by turquoise curtains.
Condo in Sarasota
5 out of 5 average rating, 24 reviews

Beachfront - 2BR - Spectacular Beach Setting

KellieRating, 5 stars3 weeks ago
Loved our stay here! The condo has everything you think you’ll need- coffee filters, laundry detergent, beach toys/chairs, boogie boards, shampoo/conditioner, beach towels, etc. The home was clean and exactly as the pictures show. The proximity to the beach was what sold us on this location, and there’s restaurants and stores within walking distance. We had a rental car, but there’s also a trolley that takes you from this area to the downtown area a few min away. All of the hosts instructions were very clear and the condo was easy to access. We expected to hear some noise here and there, but it was very quiet and peaceful. We felt so comfortable and happy here! We will absolutely come back!
Guest favorite
A sparkling outdoor pool is surrounded by lounge chairs and shaded by a thatched-roof Tiki hut. The water glistens under a bright blue sky, with fluffy clouds visible. A calm bay is seen in the background, enhancing the tranquil setting.
Condo in Sarasota
4.95 out of 5 average rating, 40 reviews

Couples getaway on Siesta Key!

StephanieRating, 5 stars1 month ago
Great place for just two. Kitchen was updated and had all you would need. Living room has comfy furniture. Bed was a King and was cozy with extra tv for nighttime wind down. Plenty of Beach towels so a short walk to the pool has you covered. Nice pool area with sun or shade. Beautiful views!!

Beachfront home rentals with a hot tub

Superhost
A modern living area features a light-colored sofa set complemented by decorative cushions. A glass coffee table sits at the center, with soft lighting enhancing the neutral tones of the space. The open layout leads to a dining area and a well-equipped kitchen in the background.
Apartment in Siesta Key
4.91 out of 5 average rating, 11 reviews

3 Bedroom 2 Bath Palm Bay Club

DonnaRating, 5 stars6 days ago
Enjoyed our stay at Palm Bay Club. Loved the bayside pool area. We had a great trip.
Superhost
A large heated pool is surrounded by a spacious limestone deck, furnished with lounging chairs and tropical plant arrangements. Sunlight reflects off the clear water, creating a serene atmosphere. The pool area is designed for relaxation and enjoyment in a private outdoor setting.
Home in Siesta Key
5 out of 5 average rating, 26 reviews

Canal home short walk to Beach & Village, Heated P

CarlyRating, 5 stars24 months ago
Can’t say enough good things about the house and Steven. The house was beautiful, it was everything we could’ve wanted and to have the additional beach supplies readily available was amazing! Steven answered so quickly and was happy to help however he could. 10/10 for us!!
Top guest favorite
A sandy pathway leads through lush greenery, providing access to a charming two-story building. The structure features a spacious balcony, surrounded by palm trees and local vegetation, under a bright blue sky with scattered clouds.
Apartment in Longboat Key
4.95 out of 5 average rating, 103 reviews

Longboat Key-OCEAN FRONT- on the beach

JimRating, 5 stars2 weeks ago
Absolutely loved our stay! The place was spotless, beautifully decorated, and had everything we needed for a relaxing getaway. The location was perfect—just steps from the beach with stunning views and peaceful surroundings. Cindy was incredibly responsive and welcoming. We’ll definitely be back—highly recommend
Guest favorite
Condo in St. Pete Beach
4.93 out of 5 average rating, 198 reviews

850 Sqft - 1 Bedroom 1.5 Bath (GULF FACING!) Condo

JessicaRating, 5 stars1 week ago
The place was just perfect! It was so clean and a great location, it’s on a stretch of beach that doesn’t get too crazy busy. The staff at the building were just as great as the host ! Would 100% stay here again
Guest favorite
The front view of a three-story home features a light-colored exterior with decorative detailing. Large windows allow for ample natural light. Lush palm trees frame the entrance, and a garage is visible below, indicating convenient parking options.
Home in Holmes Beach
4.94 out of 5 average rating, 106 reviews

The Peachy Beach House, steps to the gulf

JamieRating, 5 stars1 month ago
We had the most wonderful 5 days here. House and pool were amazing. Heated outdoor shower was great for after the beach. Beach is less than a 5minute walk away. We walked there several times at sunset and got beautiful photos. restaurants and shopping near by. we will definitely be back!
Superhost
A vibrant outdoor area features a cozy splash pool surrounded by a stylish deck. Colorful pink lounge chairs are arranged nearby, and a large, eye-catching mural depicting marine life and a ship creates a captivating backdrop.
Home in Siesta Key
4.8 out of 5 average rating, 104 reviews

Trendy & Fun Haven: Walk to Beach ~ Jacuzzi ~ Pool

SarahRating, 5 stars1 month ago
We were a group of 7 girls and had a blast at Chads place! Any issues we had were addressed and handled within MOMENTS. Home was clean, safe ash to locate, easy to get into and accurately described. House was within walking distance of everything we wanted to do (beach, bars, restaurants). We all agree we’ll return again!
Guest favorite
The outdoor area features a spacious pool and a separate spa, surrounded by manicured gardens and palm trees. A covered lanai with steps leads to the upper level of the home, which includes expansive sliding glass doors inviting natural light into the interior.
Home in Anna Maria
4.94 out of 5 average rating, 17 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

MelodyRating, 5 stars1 month ago
We had a wonderful stay at this beautiful house! This was our 5th trip to AMI and this was our favorite rental yet. Beautiful, clean home, gorgeous pool, minutes from the beach! My mom even walked to the beach in about 10 minutes. Right around the corner from ice cream, shops and rentals. We’d love to stay at this house again!
Top guest favorite
A pool area is featured, showcasing a circular hot tub adjacent to a larger pool surrounded by tropical foliage. The two-story house is visible in the background, with an American flag displayed on the balcony. Outdoor lounge chairs are arranged near the water.
Home in Anna Maria
5 out of 5 average rating, 13 reviews

CabAnna Maria Beach Block 4 Bedroom 4.5 Bath

Katrina KayRating, 5 stars1 week ago
amazing view! amazing surroundings to hike around and look at things. I've been to this house more than once and will definitely go back again. the cleaning person was so nice that she put in our groceries that we had delivered and even organized them. they're always quick to respond. very nice people! pictures are true and better in person

Pet-friendly beachfront home rentals

Superhost
A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.
Cottage in Pass-a-Grille Beach
4.81 out of 5 average rating, 276 reviews

Sunny PaG Island rental w/bikes-just steps2beach

ChristopherRating, 5 stars2 weeks ago
Great place right on Pass-A-Grille. Far enough from the restaurants to be quiet, but close enough to walk/stumble to. Beach access is very close. Parking as easy as possible. Rental was Clean and Plenty of Amenities. Would stay again.
Top guest favorite
A sheltered dining area is seen under a striped umbrella, featuring a large table surrounded by white chairs. A small heated pool is located nearby, complemented by lush greenery and colorful tropical plants lining the perimeter.
Townhouse in Siesta Key
4.98 out of 5 average rating, 49 reviews

Siesta Sunrise-Just steps to the beach and village

Akayla & BrandonRating, 5 stars1 month ago
Joe’s home is perfectly situated between the ocean and a few paces to any restaurant you’re craving. I can’t think of a better place to stay. With two little ones, the private pool was wonderful when we didn’t feel like packing up for a beach day. We can’t wait to stay here again! Honestly, the photos don’t do it justice.
Superhost
The exterior of the condo showcases a modern design with a covered porch featuring a seating area. Palm trees and landscaped greenery are present, contributing to a relaxed atmosphere. The structure features large windows, allowing natural light to illuminate the white façade.
Condo in Nokomis
4.94 out of 5 average rating, 18 reviews

Walk to the beach from this lovely 2 bedroom condo

Tiffany HopeRating, 5 stars1 week ago
This place is awesome! A nice washer and dryer, super clean, comfortable, and a cute outside sitting area. host left snacks, water, cooler, flashlight, and beach towels - very well thought out. The host was also super nice when we thought we locked ourselves out 😅 We enjoyed our stay and would love to come back.
Guest favorite
A heated saltwater pool is enclosed by a screened-in lanai, allowing for refreshing views of surrounding greenery. Lounge chairs are positioned along the pool's edge, offering a relaxing spot to unwind. Sunlight reflects off the water's surface, creating a serene atmosphere.
Vacation home in Nokomis
4.92 out of 5 average rating, 76 reviews

"Dolphin" Shore Beach Houses Resort

PromiseRating, 5 stars1 week ago
Beautiful little shack perfect for the two of us. OMG the pool is just the most relaxing place to be! This is a shared location with a few other units. Beautiful space, so close to the beach which has free parking, plenty of restaurants to choose from. This place really allows you to immerse yourself into the culture of the area. GO HERE!
Guest favorite
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, 6 reviews

The Shell House

CindyRating, 5 stars1 week ago
Very beautiful house within easy walking distance to the beach. It was very clean and the check in and out process was easy. My family and I had a great time. The beaches were beautiful and just a short walk from the house. The pool in the back yard was private and perfect for my family. The decor and landscaping was great! I highly recommend staying here. It was perfect!
Superhost
The home's exterior is softly illuminated by warm lights, highlighting the paved driveway and tropical landscaping. Tall palm trees and lush greenery surround the entrance, creating a serene atmosphere. The modern roof adds a contemporary touch, enhancing the inviting appearance of the property.
Home in Longboat Key
4.88 out of 5 average rating, 124 reviews

Summer House longboat key

LauraRating, 5 stars3 weeks ago
Enjoyed our stay at Chris's place. Pool was very clean and house was well stocked with towels, laundry supplies, etc. Kitchen had plenty pots and pans. Pool had some floats and some pool noodles. Ample seating outside for everyone. Neighborhood was very nice and we felt safe. Light switches were kind of tricky but we figured it out. Didn't stay long enough to grill but hoping to come back again and try the outside grill.
Top guest favorite
A spacious living area is highlighted by a comfortable brown leather sectional sofa, accompanied by a round coffee table. Large glass doors open to a patio area, allowing natural light to flood the room, with a serene beach scene displayed on the adjacent wall.
Home in Siesta Key
5 out of 5 average rating, 14 reviews

Key Casa on canal, 3bd 2 bath, 0,5 miles f Siesta

EvanRating, 5 stars1 month ago
The house is very convenient to the beach and to shopping and restaurants but far enough away from the main street to be very peaceful. Also, the kitchen and dining areas are large, so there is no problem having dinner "at home" for the family, if you want a break from eating out. Checking in was very easy, there are TVs in each bedroom, and the appliances, including washer and dryer all worked well.
Guest favorite
Two lounge chairs are set on a smooth patio, facing the shoreline. A cozy chair with cushions is included nearby. Lush greenery and palm trees provide shade, and a large window reflects natural light from inside the space.
Home in Englewood
5 out of 5 average rating, 34 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

RachelRating, 5 stars2 months ago
Beautiful views from this beach bungalow that provided lots of amenities - comfy beds, plush towels, well-stocked kitchen, beach chairs, etc plus extras like a bottle of wine and sunscreen. We really enjoyed our time here. The only negative was the lack of a solid door on the main bedroom. It’s a slatted closet door so it limited privacy and was not quiet if anyone was in the kitchen. Still, we’d highly recommend it for the location and the completely updated cottage!

Quick stats about beachfront rentals in Siesta Key

  • Total rentals

    170 properties

  • Nightly prices starting at

    G$25,178 GYD before taxes and fees

  • Total number of reviews

    6.7K reviews

  • Family-friendly rentals

    130 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    140 properties have a pool

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