Beachfront holiday rental in Siesta Key

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Popular amenities for Siesta Key beachfront rentals

Pet-friendly beachfront home rentals

Top Guest favourite
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.
Guest favourite
Cottage in Pass-a-Grille Beach
4.88 out of 5 average rating, 170 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

KatieRating, 5 stars2 weeks ago
Lisa was a great host, and paradise by the beach is an awesome place to stay. My family of 4 (2 adults and our older teens) just loved being able to have a lot of space (compared to the hotel rooms on st Pete beach) and a full kitchen and a close walk to the beach. The kids loved riding the bikes to get an ice cream at night, and it was so easy and convenient to pack up the chairs and umbrella and walk over to the beach. The walk is actually shorter than the resorts we have stayed at on spb. It was kind of like settling into our home by the beach—very comfy and convenient with everything we needed. Lots of tvs, lots of space, easy to get around. I also liked having a fully equipped kitchen—only made dinner one night, but everything we needed was there! We’d definitely again and prefer it to the other resorts we have stayed at. It’s less expensive, more convenient, and a lot more space. Thank you so much, Lisa! We hope your space is available next time we come down!
Guest favourite
Home in Anna Maria
5 out of 5 average rating, 6 reviews

The Shell House

CindyRating, 5 stars2 weeks 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!
Guest favourite
Condo in Treasure Island
4.9 out of 5 average rating, 126 reviews

Waterside Studio in the heart of TI, walk to beach

FrancineRating, 5 stars3 days ago
My husband and I needed a little staycation after a stressful few months. The little apartment at the beach was perfect. The location was beautiful despite the fact that the area is still recovering from a few hurricanes last year. The host was also very helpful and gave some great recommendations. The only negative thing that I can say is that my stay was too short. I look forward to staying there again.
Guest favourite
Home in Englewood
5 out of 5 average rating, 34 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

RachelRating, 5 stars3 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!
Guest favourite
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.
Top Guest favourite
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
Guest favourite
Home in Siesta Key
4.86 out of 5 average rating, 14 reviews

Sweet Siesta Cottage

ByronRating, 5 stars1 month ago
Billie was an amazing host! She was extremely flexible with check-in and the cottage was great. We come to Siesta Key yearly and try to stay in walking distance to everything and this was block away from the beach and 10-15 minute walk to downtown. We didn't have car but there's parking available if needed. Will be our go-to spot going forward!

Beachfront home rentals with a pool

Guest favourite
Condo in Siesta Key
4.94 out of 5 average rating, 18 reviews

Penthouse Expansive Ocean Views

AimeeRating, 5 stars1 month ago
Brenda’s place was just as listed. Great location, clean, great space to call home for the week. Within walking or short drive to many restaurants and shopping areas. Walk to the beach was easy especially with all the beach supplies in the condo. Brenda was also very responsive when I reached out with clarifying questions.
Guest favourite
Condo in Siesta Key
4.94 out of 5 average rating, 96 reviews

The Honeymoon Suite on Siesta Key Beach

AshleyRating, 5 stars1 month 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 favourite
Condo in Siesta Key
4.84 out of 5 average rating, 236 reviews

Cozy 1BR Beach Condo on Siesta Key!

RachelRating, 5 stars2 weeks ago
We had a wonderful time at Bill's place, very cozy and had everything we needed. Loved being able to walk to the beach and spent some time at the pool, we had so many more things we wanted to do and not enough time in the day!
Guest favourite
Condo in Siesta Key
4.95 out of 5 average rating, 19 reviews

Siesta Key GULF SIDE #100-Peaceful, Private Condo

MarthaRating, 5 stars10 months ago
Renee is an amazing host. When we told her we were flying in Friday night and getting a hotel because the flight was cheaper she offered to let us check in Friday night for no charge. Renee checked in with us a few times throughout the week to see if we needed anything. We look forward to vacationing with her again in the future.
Superhost
Cottage in Siesta Key
4.86 out of 5 average rating, 166 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Lauren Rating, 5 stars1 month ago
The cottage was the perfect beach stay. Clean, easy access to the beach, and all the amenities of home. We especially enjoyed eating breakfast out by the pool overlooking the golf and bringing dinner down to the beach for sunset. Definitely worth it.
Guest favourite
Condo in Siesta Key
4.95 out of 5 average rating, 76 reviews

Casa Mar Steps 2 Siesta Key, Pool, Tennis, & More!

AlliRating, 5 stars3 weeks ago
After two years of visiting this has become my one week oasis once a year! The pool is basically your backyard. The room itself is small but very homey, cozy and perfect for 2 people. Easy to cook dinner or just pop in and out for easy lunches. IT IS SO NICE being steps from the pool and just a minutes in sand to get to the ocean waters. Beach chairs are free to use. Towels are provided. The most precious clothes lines hangs out back for easy and free drying! The community is sooo kind. Do yourself a favor and say hi! You’ll be amazed by the lifelong friendships you can make! Restaurants are close by and the community is always willing to help you with recommendations! Hosts are quick to respond, we had a microwave issue and it was resolved within 12 hours! Very easy to communicate with! Overall I love our little community for the one week I get :) it will now always be a yearly vacation for me. I’ve met some lifelong friends!
Guest favourite
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 favourite
Condo in Longboat Key
5 out of 5 average rating, 7 reviews

Perfect Beach View Large 2 bedroom

JoshRating, 5 stars2 days ago
Stunning apartment. The view is incredible and the furnishings are all top quality. Highly recommended.

Private beachfront home rentals

Guest favourite
Condo in Siesta Key
4.88 out of 5 average rating, 50 reviews

Enchanting Coastal Ambiance & Breathtaking Sunsets

LillieRating, 5 stars2 weeks ago
home was very clean and cozy!! everything was in walking distance and close to the beach, restaurants and shops were walkable distance 😊
Top Guest favourite
Apartment in Longboat Key
5 out of 5 average rating, 27 reviews

Turquoise Gem 1st Floor

KinsleyRating, 5 stars1 week ago
The turquoise gem is truly a gem, I’m so thankful we found this place! It’s very cozy & clean. Although, I would recommend bringing some slippers or wearing socks, I get why there’s not a lot of rugs (sand & such) but the floor isn’t the most comfortable walking around barefoot. The location is perfect, and super close to a convenient store & restaurants. The beach is gorgeous. Loved it here & we would totally stay again!☺️
Superhost
Apartment in Siesta Key
4.78 out of 5 average rating, 23 reviews

Condo Kokomo - stay ON the beach in Siesta Key!

LauretteRating, 5 stars1 month ago
The condo is directly across the street from the beach and within walking distance of the restaurants and shops. It has a great little patio that we sat on to eat breakfast and to enjoy an evening cocktail. There is a closet with beach chairs, umbrellas, sand toys and coolers and Amelia provided beach towels. It was perfect!
Top Guest favourite
Condo in Siesta Key
4.93 out of 5 average rating, 43 reviews

Siesta Oceanview Retreat-1 min walking to beach

DougRating, 5 stars1 week ago
Really nice home, was very clean when we arrived and had everything we could have needed at a home away from home. Fantastic location, short walk across the street and you’re at the beach. Would definitely recommend and stay here again. Host was great as well and very responsive with clear instructions.
Guest favourite
Condo in Siesta Key
4.94 out of 5 average rating, 204 reviews

Siesta key getaway!

LoriRating, 5 stars3 weeks ago
My husband and I stayed for eight days to celebrate our anniversary. We had a great week. The location was great, host Debbie met us at check-in with our key and walked us around the condo and pool area. Public transportation was right out in front of condo. Many good restaurants in walking distance and beautiful beaches.
Top Guest favourite
Apartment in Lido Key
5 out of 5 average rating, 10 reviews

Cozy 1 bedroom a block from Lido Beach

JudyRating, 5 stars3 weeks ago
We had a great stay. We were there to have a relaxing beach vacation and were so happy to see all of the items we needed to spend time at the beach. The place is super comfy, clean, and quiet. Would definitely stay here again!
Guest favourite
Cottage in Siesta Key
4.88 out of 5 average rating, 315 reviews

Cottage on Siesta Key Beach

CherylRating, 5 stars4 days ago
This whimsical beach cottage was exactly what we needed after Hurricane Milton. The house was stocked with everything we needed to feel at home. The beds were comfortable and the location was perfect. It was unfortunate to see the devastation from the hurricane around the property, but thankfully Andrew’s place was seemingly untouched. We’re very happy for you! Thank you for providing a great place to enjoy the bay and the beach!
Apartment in Sarasota
4.9 out of 5 average rating, 105 reviews

Siesta Key Village-Suite #1: A block to the Beach!

MelanieRating, 5 stars1 month ago
Visited siesta key for a long weekend and this place was the perfect spot to stay. The location is fantastic, right on the main strip where all the shops and restaurants are, and an easy 5 min walk to the beach. The one caveat I had is that the listing states they offer early luggage drop off for guests’ convenience. My plan was to drop off my bags and then keep myself busy until check in at 4pm. When I had messaged on the day of check in, they said they could not accommodate that, HOWEVER, they promised to let me know as soon as the airbnb was clean and ready for me to check in. I got into town around 10:30am and they let me check in at around noon. So they more than met me halfway, and I was very appreciative of that! The space was very clean, and the beach chairs/umbrella/cooler were a nice touch! Live music can be heard until about midnight due to proximity to several restaurants, but it wasn’t bothersome at all. Would definitely stay here again.

Quick stats about beachfront rentals in Siesta Key

  • Total rentals

    170 properties

  • Nightly prices starting at

    $199 NZD 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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