
Home rentals with a pool near Crescent Beach
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Top-rated rentals with a pool near Crescent Beach
Guests agree: these stays are highly rated for location, cleanliness, and more.

Luxury Queen Suite
Wake up with a fresh cup of coffee, then take a short stroll to Siesta Key’s world-famous white sands. Feel the cool, powder-soft quartz beneath your feet as the ocean breeze melts your worries away. Spend your days basking in paradise, swimming in crystal-clear water and watching breathtaking sunsets. Afterward, return to your spotless luxury condo, refresh, and enjoy Siesta Key’s vibrant nightlife. A true beach oasis in the perfect location—book now before it’s gone! Note: No parking available

Relax in a Private Tropical Retreat on Siesta Key!
Your dream vacation awaits with a renovated, spacious, and private single-level house. It's a perfect getaway for a relaxing vacation! Enjoy all the comforts of home while being just a short walk away from restaurants, bars, and Siesta Key's beautiful white sand beaches. Nestled on a quiet tree-lined street and tropical gardens, this retreat offers tranquility and serenity. The community boasts a large heated pool and intercoastal waterway pier, ideal for afternoon fishing or sunset beverages!

Pool Courtyard, patio w/ fire pit, 2 mls downtown
Enjoy this unique courtyard-style Spanish colonial home just steps to Sarasota Bay and 2 miles from downtown. The property consists of a 2 bed / 1 bath main house AND a detached studio. Everything pictured is yours to enjoy, nothing is shared. The houses are separated by a quaint & private pool courtyard w/ outdoor shower. Capture a photo of the local peacocks, eat fresh mangos from the yard, catch a sunset over the bay, or enjoy the sun by the pool listening to the Zen fountains.

On the Beach; Siesta Key SunBum Studio
Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta 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, 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!

Palm Bay Club! Resort Style Living on Siesta Key!
Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

Sea Shell Ocean view On Beach Walk everywhere Pool
Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 325+ reviews that ave FIVE STAR!

Cottage on Siesta Key Special December Pricing
Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

203 Luxury Condo With Ocean View, Heated Pool +
Luxurious apartment style condo on Siesta Key Beach, Sarasota Florida overlooking the quartz white sand and turquoise waters of the #1 beach in the USA. Enjoy exquisite ocean views from the balcony or just a few steps to the beach. Our gated community positions you steps away from whatever your heart desires (pool, ocean, grocery store, restaurants, live music and local shops). Your options are limitless on Siesta Key.

Siesta Key Beach Front Condo
Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

Siesta Dunes 1st Floor Beach Front Retreat + Bikes
Steps from the beach, this spacious 2 bedroom condo has everything you will need for your Siesta Key vacation. Located in the beautiful gated community of Siesta Dunes, with heated salt water pool, and its own private beach access, complete with beach chairs, umbrellas and towels. Stroll though the well-manicured grounds on your way to the pool, the sundeck and the beach.

Oct SALE! Private Sarasota #1 Luxery beach Villa
BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

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.
Popular amenities for rentals with a pool near Crescent Beach
House rentals with a pool

Family Retreat w/Pool&HotTub 5 min to Siesta Key!

The Sand Castle - Backyard Oasis Mins from Siesta!

Relaxing 3BR/2Ba Oasis with Heated Pool.

2BR/2BA home w/ heated pool, 5 min to Siesta Key!

The Palms Away

Private Siesta Beach House Oasis with Heated Pool.

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
Condo rentals with a pool

#1 Beach- Super Clean- 2br/2bth Townhouse- 1400sf

Crystal House on Siesta Key Beach

Sarasota Surf & Racquet Club Siesta Key Condo

Siesta Key Spacious, Modern 2 bed, 2 bath condo

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Anchor house +6 min. from Siesta Beach+heated pool

Sarasota Surf & Racquet Club Siesta Key Condo

Oceanview: Open Tonite, $95/nt + Fees, Arrive Now!
Other vacation rentals with a pool

2 BR condo in Siesta Key w/ Private beach access

Toes In The Sand | Private Pool, Walk to Beach!

Private Beach Access. Pool. Grill. Siesta Key

Newly Remodeled Luxury Beach Villa on Siesta Key!

Johnnys Island Palm | Walk to Beach & Dining

Amazing beach view! Entire unit renovated!

Siesta Key Beachfront Condo - Private beach access

Siesta Key*PRIVATE BEACH*Gulf Side*Heated Pool
Quick stats about rentals with a pool near Crescent Beach
Total rentals
1.2K properties
Nightly prices starting at
$98 CAD before taxes and fees
Total number of reviews
28K reviews
Family-friendly rentals
1K properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with dedicated workspaces
540 properties have a dedicated workspace
Destinations to explore
- Pet-friendly rentals Crescent Beach
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- Rentals with pools Siesta Key
- Rentals with pools Sarasota County
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- Anna Maria Island
- Siesta Beach
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
- Lido Key Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Gulfport Beach Recreation Area
- Jannus Live
- Manasota Key Beach
- North Beach
- River Strand Golf and Country Club
- Splash Harbour Water Park
- Englewood Beach
- North Beach At Fort DeSoto Park
- Point Of Rocks
- Don CeSar Hotel
- Lakewood National Golf Club