Holiday rentals with a pool in Osprey

Lake View, 6 Miles From Beach

-Located inToscana Isles (gated community with heated infinity pool, gym, tennis/pickleball/bocce ball courts, playground, dog park, billiard room, and monthly events) -Backs up to 1 of 3 lakes (kayaking and fishing allowed, 2 kayaks, 2 fishing poles and tackle box included) -6 Miles from Nokomis Beach, 6.8 miles to Venice and dog beach, the only pet friendly beach in the area (4 beach chairs, umbrella, cooler, wagon and beach bags included) -Close to Legacy Trail and Oscar Scherer State Park

Great price for the summer 3/2 Beach House

3/2 beach house newly renovated. Only 8 minute drive from Nokomis beach and central to Venice with its wonderful restaurants and bars . Located in a friendly quiet neighbourhood the perfect place to unwind and relax. Close to Casey key and Gulf Harbour Marina with boat rental and public dock. 2.5 miles from Nokomis Grill and 5 miles from Venice Beach. Private parking for a Boat or small trailer plus. Visit our new social media Casas Bonita, Nokomis FL http://airbnb.com/h/casasbonitas

Paradise with a pool, pier and private beach area

Intercoastal, Blackburn Bay waterfront home with boating facilities near Casey Key and Siesta Key. On a point facing the setting sun. This is simply paradise. The pier is long, and the water deep enough to handle most boat docking needs. The large, heated pool is a few steps from the screened lanai and the deck beckons "come watch the sunset". And while it won't replace one of the large beaches on the key, you can lay or play on our beach hidden by mangroves, and easily launch kayaks, etc.

Sarasota Escape | Minutes to Beaches + Downtown

HEATED POOL. NONTOXIC + 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.

Family Getaway/Beautiful House/Beach/Private Pool/

Beautiful House with 3 bedrooms, heated pool, mini golf and two-car garage. Great location. five-minute drive to the beach. near shopping plazas, restaurants, and the famous Legacy Trail perfect for biking, running, and more. Situated at a dead-end in a peaceful community. Lots of outdoor space around the house with beautiful palm trees and a large patio. bicycles, board games, cornhole, a gas grill, and more at your disposal. Lots of places to visit in the Sarasota and Venice area.

The Pineapple Escape

The Pineapple Escape is the perfect gateway vacation house that has everything you're looking for. With a heated pool for access year round and beautiful kitchen for all your desires. Just a short drive from some of Florida's finest beaches, such as Nokomis Beach on Casey Key,Venice Beach and about 15 minutes drive to #1 beach in US, Siesta Beach in Sarasota,. You'll find this neighborhood to be quite serene and peaceful. Book today to start making memories at The Pineapple Escape.

Creekside Paradise I

The 1970 sqft living space hosts 3 bedrooms, 2 bathrooms, an open living room with attached ‘library’, a dining area, as well as a fully equipped kitchen. From the caged pool area you have a view of the North Creek and our Boat Dock. The pool can be electrically heated and measures 32.80ft in length/13.12ft in width. You enter Creekside Paradise I thru the attached 2 car garage, where you can find the beach equipment (chairs, umbrella, cooler).

Luxury Pool Home by Siesta/Lido

Stylish 3BR/3BA+office centrally located Sarasota home with private heated pool, spa, and fenced yard—just minutes to Siesta Key & downtown. A short bike ride to Arlington Park and Southside Village. Features upgraded kitchen, smart features and putting green. Bedroom not pictured has a bunk with a queen on bottom, twin XL on top. Perfect for families or couples looking to relax, work remotely, or explore Sarasota’s best spots

Spacious 2 Bedroom Home | Near Beach | Heated Pool

This beautiful home just minutes from the beach offers 2 spacious king bedrooms, a queen sofa bed in the large open living area, and a full kitchen ready for entertaining. Gather your family around the dining room table for food and games and then relax on the lanai or have a float in the pool. The hosts provide Margaritaville frozen concoction machine, 2 bicycles, beach chairs, beach towels, shark tooth tools, and more.