
Home rentals with a pool near Lido Key Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Lido Key Beach
Guests agree: these stays are highly rated for location, cleanliness and more.

*NEW-Prime Spot St. Armands/Lido Key 1st fl w/pool
*LOCATION* *LOCATION* A block to St Armands Cir. and their 130+ boutique storefronts, dining and experiences. White sandy Lido Beach is 6 minutes away all via sidewalk. Fully stocked kitchen and hall closet incl. beach buggy, cooler, chairs umbrella. Large bedrooms with closets, each having an en-suite bath. Private/quiet lanai. Your front door is 3 units away from the pool/hot tub. 1 Reserved parking space. Free trolley to take you to downtown Sarasota! 15 min from SRQ Airport and 60 from Tampa

Longboat Key-OCEAN FRONT- on the beach
My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

2 BR Beachy Speakeasy | Rooftop Deck | Lido Beach
Step into your WINTER Holiday with a Beach Vacation! Now booking Spring! Reserve your March & April dates! Picture this: a rooftop deck, just a 5min walk to the pristine sand of Lido Beach, and surrounded by the charm St Armand's Circle with boutiques, and eateries, all within walking distance. Forget the conventional - this condo's got a secret. Tucked behind an unassuming door lies a vibrant space, drawing inspiration from speakeasy culture fused w/ a beach vibe. Your adventure starts now

The Cottage At Central Park
There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Lido-Key- Tiny Studio Holiday Cottage-A
We are Open after Hurricane Helene! **No Kids allowed** Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

Sarasota Escape | Minutes to Beaches + Downtown
HEATED POOL + ECO FRIENDLY. Relax with the whole family or bring that group chat trip to life at this peaceful retreat in the heart of Sarasota. Boasting a spacious and nature-inspired design, this home is a short drive to several world class beaches, the downtown Sarasota arts district, 5 star dining, shopping and more. The home is also located within walking distance of a park complete with playground, public pool, tennis + basketball courts, workout area and walking trails.

Lido Key/St Armand's Retreat
a small studio condo: a fairly private bedroom (no door) and a sleeper sofa in the living room; best for 2, but sleeps 4. There is a very small screened balcony. The one bath has a shower. The guest section of the closet has hanging space, several shelves and drawers; the bedside tables have 4 compartments each. The kitchen has basic kitchenware; we provide sheets, towels, beach towels, and basic bathroom necessities. Looking for Budget accommodations close to beach

Oceanfront Open Mon - Fri, $185/nt + Fees!
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 loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort!

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!

Sunset and beach view from your balcony Unit 403
A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Seabreeze Serenity: Lido Key Poolside Paradise
Exclusive Amenities Include: • Private Heated Pool • In-ground spa • 3 Bedrooms, 2 Full Bathrooms • 2 King Beds & 2 Twin Beds, Sleeper Sofa (Sleeps 8) with linens provided • Spacious Outdoor Lounging Area • Free WiFi & HDTV’s • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Caddy Provided • Gas Grill

Sea Esta | Private Saltwater POOL + Putting Green!
BNB Breeze Presents: Sea Esta! Experience this stunning home in the heart of Sarasota, located just 10 minutes away from Siesta Key Beach! From the gorgeous interior, to the INCREDIBLE outdoor oasis, this home has it all! • Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st • E-Bikes (For Rent) • Resort-Like Back Yard w/ a Pergola, Turf + Putting Green • Pool + Beach Supplies • Fun Outdoor Swinging Dining Table
Popular amenities for rentals with a pool near Lido Key Beach
House rentals with a pool

Paradise on Prospect w/ Htd Saltwater Pool

Coastal Luxe, SaltPool/Spa, 5miles to Siesta

Summer House longboat key

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Heated Pool • Near Siesta Key Beach & Downtown

The Blessing House- Htd Pool/Spa, Close to Beaches

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough
Apartment rentals with a pool

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

Luxury 3/3 Margaritaville Resort

6 min to Siesta Beach | Heated Pool | Lake View

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Cottage on Siesta Key Beachside & Stunning sunsets

Near beach. Daily rentals. Pool. king bed

5213A Calle Menorca - Siesta Key Village Condo

Beachfront Escape – Private Balcony, Gulf Views
Other holiday rentals with a pool

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Steps from Lido Beach & St. Armands Circle

Condo on Lido Beach-Sarasota

Zen in Paradise-Sarasota

Poolhouse 1/1, 4 min from Siesta

Mid-Century Modern, Pool, Mins to Siesta Key Beach

Chic Beach Condo>>Best Location On Lido Keys

New Modern Longboat Key*5 Steps to Sand*Heatd Pool
Quick stats about rentals with a pool near Lido Key Beach

Total holiday rentals
Explore 160 holiday rentals in Lido Key Beach

Nightly prices starting at
Lido Key Beach holiday rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 3,500 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
160 of Lido Key Beach holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Lido Key Beach rentals

4.8 Average rating
Lido Key Beach stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Rentals with pools Sarasota
- Rentals with pools Sarasota County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
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- Raymond James Stadium
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- Coquina Beach
- Vinoy Park
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- Gulfport Beach Recreation Area
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- North Beach
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- Englewood Beach
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