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Condo vacation rentals in Siesta Key

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Top-rated condo rentals in Siesta Key

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Condo in Siesta Key

4.82 out of 5 average rating, 234 reviews

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

We pay your AIRBNB service fees for you! Updated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. The “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023! 2 min drive or 10 min walk to beach! Enjoy FREE Kayaks, SUPs & Tiki Huts!

May 10 – 17

€ 190 per night

Condo in Siesta Key

4.83 out of 5 average rating, 286 reviews

[Sunny in Siesta] King bed+5 minute walk to beach

Your relaxing beach vacation awaits! Enjoy the island life from a freshly remodeled condo. Quick stroll to the #1 beach in the US. Public Access #12 (5 min walk) or hop on the free trolley to Siesta Beach & the Village. Can’t beat this location...Walk to Crescent Club, Captain Curt’s, Big Water Fish Market, Daquiri Deck & more. Beach gear includes- wagon., 2 chairs, small cooler and beach towels. 2 Bikes available to rent ($35 per bike) King bed BEAUTY REST BLACK & queen sofa bed.

Oct 28 – Nov 4

€ 266 per night

Condo in Siesta Key

4.96 out of 5 average rating, 275 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Nov 21 – 28

€ 331 per night

Condo in Siesta Key

4.83 out of 5 average rating, 122 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Sarasota Surf and Racquet Club is located on Siesta Key's award winning Crescent Beach. Our condo unit has all of the amenities of home for your convenience. The master bedroom has a king sized bed and it's own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

Nov 2 – 9

€ 454 per night

Condo in Sarasota

4.95 out of 5 average rating, 123 reviews

Cozy Beach Side 1BD/2BA, Walk to Beach & Pool

- First Floor 1 Bed/2 Bath condo w/ One King Bed( STEARNS &FOSTER MATTRESS) + One Sofa Bed - 3 Minute Walk to Private Access World Renowned Siesta Beach and Saltwater Heated Pool - Beach Side of Midnight Pass Rd - Beach Gear Provided - Patio Area - One Parking Space out front ( max to mid SUV = size similar Honda pilot) - Restaurants, bars, ice cream and seven Eleven, grocery & liquor store , pharmacy+ shops right across the street! Go to places by walking or riding a free Trolley.

Sep 13 – 20

€ 231 per night

Condo in Siesta Key

4.82 out of 5 average rating, 131 reviews

The Key to a Great Vacation!

Welcome to our one bedroom, one bath (4 piece) main floor condo. Recently renovated. Freshly painted with new furniture, a brand new king size memory foam mattress with contemporary decoration (with queen size pull out couch). Easily accessible with no steps to climb and close, convenient parking right outside the front door. Quiet, peaceful and near both Siesta Key Beach and the condo pool ensure a wonderful vacation. Walk across the street and enjoy one of the best beaches in the world.

Nov 2 – 9

€ 230 per night

Condo in Longboat Key

4.97 out of 5 average rating, 148 reviews

Charming Condo on the Coast!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with complimentary chairs and umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Oct 24 – 31

€ 349 per night

Condo in Sarasota

4.89 out of 5 average rating, 127 reviews

Gateway to Siesta Key 1/2 mile to the Beach!

Super comfy and newly updated 2 bedroom/2 bathroom fully-equipped condo that sleeps 4 - only 1/2 mile from the Gulf of Mexico! Located in a small and quiet complex with very convenient access to the beach as well as all of Sarasota's shopping and dining (without beach traffic). Our condo is exceptionally clean, well-kept and has all the comforts of home on your tropical getaway. Minimum age of primary renter is 25 years old. Proof of age required.

Aug 21 – 28

€ 171 per night

Condo in Siesta Key

4.87 out of 5 average rating, 210 reviews

Siesta Key Beach Community!

Two bedroom, one bath fully furnished condo. Fantastic location on Siesta Key. local bus goes to nearby Siesta Village & #1 beach in the US. Heated pool, tennis court and clubhouse. BBQ, picnic area and fishing pier located on the bay side. one king bed and one full. Siesta beach is less than a mile with free parking and crescent beach is a 10 minute walk.

Jun 6 – 13

€ 132 per night

Condo in Siesta Key

4.85 out of 5 average rating, 131 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

A cozy Siesta Key ground floor condo unit w 2 bedrooms & 1 bath on the trolley line. Has all the amenities you need for a relaxing beach vacation and your day at the beach. Located conveniently to Crescent beach w access to the south and Siesta Key public beach to the north. Trolley stops right out front. Assigned parking spot directly in front of the unit.

Nov 16 – 23

€ 192 per night

Condo in Siesta Key

4.96 out of 5 average rating, 105 reviews

Siesta Key Condo. Checkout our great rates!

Our beautiful Siesta Key condo is located a short stroll from the famous Siesta Key beach with its beautiful quartz sand and amazing sunsets. The Midnight Cove II condominium complex has private beach access with outstanding amenities and is very family friendly, come and enjoy the natural beauty this complex and all Siesta Key has to offer.

Aug 26 – Sep 2

€ 188 per night

Condo in Siesta Key

4.96 out of 5 average rating, 353 reviews

Siesta Gardens @ Siesta Key Village

Overall, Siesta Key is in fine shape after Hurricane Ian. Our unit has electric and water now. Cute little condo located directly in the heart of Siesta Key Village. Seconds away from all the shops, restaurants, and the Siesta Key night life. This condo is also conveniently located within walking distance from the #1 Best Beach in America.

Sep 2 – 9

€ 257 per night

Vacation rentals for every style

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Popular amenities for Siesta Key condo rentals

Free parking on premises

Air conditioning

Condo rentals with a pool

Condo in Siesta Key

4.96 out of 5 average rating, 103 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Apr 18 – 25

€ 414 per night

Condo in Longboat Key

4.93 out of 5 average rating, 144 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Oct 27 – Nov 3

€ 322 per night

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Nov 13 – 20

€ 145 per night

Condo in Siesta Key

4.92 out of 5 average rating, 180 reviews

Bright and Beachy - Steps to the Water!

Sep 30 – Oct 7

€ 359 per night

Condo in Siesta Key

4.89 out of 5 average rating, 118 reviews

Siesta Key Beach Escape

Oct 8 – 15

€ 402 per night

Condo in St. Pete Beach

4.91 out of 5 average rating, 211 reviews

Sunset Beach Condo in Treasure Island

Sep 14 – 21

€ 139 per night

Condo in Siesta Key

4.93 out of 5 average rating, 215 reviews

Private Siesta Key Escape

Aug 2 – 9

€ 432 per night

Condo in Siesta Key

4.82 out of 5 average rating, 193 reviews

New: Cozy 1BR Beach Condo on Siesta Key!!!

Jan 1 – 8

€ 259 per night

Condo rentals with a hot tub

Condo in Siesta Key

4.97 out of 5 average rating, 110 reviews

Siesta Key For Me @ The Palm Bay Club

Dec 13 – 20

€ 355 per night

Condo in Siesta Key

4.92 out of 5 average rating, 137 reviews

Siesta Key Serenity At The Palm Bay Club

Nov 17 – 24

€ 341 per night

Condo in Longboat Key

4.82 out of 5 average rating, 159 reviews

Updated Beachfront Condo at Prestigious Long Boat

Mar 15 – 22

€ 725 per night

Condo in Bradenton Beach

4.91 out of 5 average rating, 129 reviews

Beachfront condo in paradise

Mar 8 – 15

€ 553 per night

Condo in Holmes Beach

4.96 out of 5 average rating, 116 reviews

Beautiful beachfront condo for perfect vacation

Jul 20 – 27

€ 289 per night

Condo in Bradenton

4.98 out of 5 average rating, 169 reviews

Shorewalk full condo IMG Beaches Anna Maria

Dec 1 – 8

€ 190 per night

Condo in Bradenton

4.98 out of 5 average rating, 144 reviews

Luxury 3/3 Margaritaville Resort

Aug 19 – 26

€ 310 per night

Condo in Ruskin

4.93 out of 5 average rating, 111 reviews

Beach Condo with water view!

Apr 6 – 13

€ 132 per night

Family-friendly condo rentals

Condo in Siesta Key

4.93 out of 5 average rating, 182 reviews

Steps away from beach and village! #1 in Siesta!

Mar 14 – 21

€ 664 per night

Condo in Bradenton Beach

4.82 out of 5 average rating, 217 reviews

A+ location! Steps to beach, walk to Bridge St! #1

Oct 30 – Nov 6

€ 252 per night

Condo in Treasure Island

4.91 out of 5 average rating, 159 reviews

Gorgeous One Bedroom on Sunset Beach #52

Oct 6 – 13

€ 188 per night

Condo in Holmes Beach

4.91 out of 5 average rating, 158 reviews

Anna Maria Beach Place...footsteps to the sands

Apr 3 – 10

€ 269 per night

Condo in Treasure Island

4.9 out of 5 average rating, 132 reviews

Luxury Beachfront Condo with Spectacular Sunsets!

Oct 29 – Nov 5

€ 230 per night

Condo in Sarasota

4.97 out of 5 average rating, 66 reviews

Location,Location,Location-Beachfront-Siesta Key

Nov 19 – 26

€ 443 per night

Condo in Sarasota

4.84 out of 5 average rating, 73 reviews

5213B Calle Menorca - Siesta Key Village Condo

Nov 13 – 20

€ 310 per night

Condo in Siesta Key

5.0 out of 5 average rating, 48 reviews

☀️ Beach & Pool Open! Beachfront Penthouse. Chairs, Wifi

Dec 28 – Jan 4

€ 778 per night

Quick stats about condo rentals in Siesta Key

Total rentals
820 properties
Rentals with a pool
640 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
670 properties are a good fit for families
Total number of reviews
13K reviews
Nightly prices starting at
€ 65 before taxes and fees

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