Holiday rentals with a pool in Ruskin

4.94 out of 5 average rating, 120 reviews

Townhouse in Anna Maria

Green Jacaranda AMI Duplex A, 5 min walk to beach

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

4.94 out of 5 average rating, 36 reviews

A window with sheer curtains frames a scenic view of the canal and a palm tree. Below, an air conditioning unit is visible next to a bedside table that holds a decorative vase. A patterned quilt covers the spacious bed.

Condo in Ruskin

Ruskin Little Harbor condo steps from beach

Welcome to the Inn on Little Harbor Resort. Kick back and relax in this fully renovated studio apartment with canal view. From patio or front window you might see a dolphin, a manatee or a pelican. This beach style studio sleeps four and is a 2 minute walk to the private beach. The resort has two heated pools, a hot tub, restaurants , live music and much more. From your patio you can see the sunrise over the canal in the morning or unwind with a glass of wine at the end of a memorable day.

4.75 out of 5 average rating, 163 reviews

Condo in Ruskin

Little Harbor Resort #109 Tampa Bay FL Beach, Pool

Little Harbor Resort is a paradise packed with amenities. Enjoy 2 pools, Jacuzzi, Beach on Tampa Bay (not Gulf), 2 restaurants, Tiki Bar, tennis, pickleball, basketball, playground, fishing charters, sightseeing cruises, and Freedom Boat Club. The Inn at Little Harbor River Delight Studio is a ground-floor, non-smoking studio which features a kitchenette, fridge, microwave, sink, in counter hotplate, dishwasher, coffee maker with two luxurious queen beds, and captivating island decor.

4.95 out of 5 average rating, 148 reviews

Home in Apollo Beach

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

A contemporary living area features a navy blue sofa and an armchair, complemented by a round woven coffee table. Abstract ocean-themed artwork decorates the walls. A dining area with high-backed chairs can be seen in the background, alongside a well-equipped kitchen with wooden cabinetry.

4.94 out of 5 average rating, 114 reviews

Still Waters Townhome, Sunrise and Sunset Views

Elegant home with 4 balconies, 2 overlooking water. Sunset and sunrise views. Gourmet kitchen, granite countertops, cooktop range, stainless steel appliances. Coffee maker, tea kettle, Nutra-bullet, toaster and more. Each room has a large flat screen smart TV. Bright, modern, immaculate. Wireless internet, Ethernet and Netflix. Washer and dryer on main level. Five minute walk to white sand private beach, complimentary umbrella and chairs. No smoking, no pets, no events.

A marina scene showcases a collection of boats anchored along calm waters, surrounded by lush palm trees. The sky is partly cloudy, reflecting soft light over the tranquil setting. The marina is nestled against a backdrop of greenery, offering a peaceful coastal ambiance.

4.78 out of 5 average rating, 110 reviews

Sunrise Marina View - Water Toys Included - 1 Dog

Hello and welcome to Little Harbor-approximately 45 minutes South of Tampa (TPA) tucked away just West of Ruskin , FL. 124 acres with 3 miles of waterfront, 1/2 mile of East facing butter-soft white sand of which is private to owners and their guests. With two marinas, 250 foot fishing pier, heated pool with hot tub, basketball courts, pickle ball court, beach volleyball, two restaurants, plus local golf and family theme parks- what more do you need for the ideal vacation.

A spacious living room is illuminated by natural light, featuring a large flat-screen TV mounted on a wooden console. Two comfortable chairs and a coffee table sit on a textured area rug, while sliding glass doors open to a scenic balcony area with seating.

4.98 out of 5 average rating, 56 reviews

Waterfront Townhome @ Little Harbor

Relax, unwind, and enjoy this peaceful, waterfront townhome at Little Harbor. Amenities include: private pier, private beach, pool, jacuzzi, gym, tennis/basketball/pickleball courts, playground, and access to community dock for launching kayaks. Watch the beautiful sunset while listening to live music at Sunset Grill and Beach Bar or catch some dolphins while dining at Hooks Waterfront Bar and Grill. Little Harbor Marina on-site features boat rentals and fishing charters.

4.86 out of 5 average rating, 164 reviews

Apartment in Ruskin

Sunset Del Mar (studio with a view)

***UPDATED***Living the Florida lifestyle right on beautiful Tampa Bay. The Inn at Little Harbor is a secluded resort style community offering waterfront accomodations with amenities that include 2 heated pools, jacuzzi, tennis courts, a beautiful sandy beach, 2 full service restaurants/bars with live music,kayak and boat rentals and fishing charters and some of the most beautiful sunsets you have ever seen. Amenities are within walking distance from your doorstep.

4.94 out of 5 average rating, 155 reviews

The backyard features a heated pool with a unique shape surrounded by palm trees and vibrant flowers. Comfortable loungers are arranged for relaxation, while a thatched-roof gazebo offers shade. A spacious patio provides room for gatherings, enhancing the outdoor living experience.

Home in Apollo Beach

*Apollo Escape* – Canalfront Home + Private Pool

Escape to this canalfront pool home—perfect for families or groups looking to unwind and reconnect. With 4 bedrooms, 2 kitchens, a game room, and a private dock, there’s space for everyone to relax. Swim in the pool, grill in the backyard, or enjoy movie night in one of two living rooms. Just 30 minutes from Tampa and minutes to beaches, marinas, and waterfront restaurants—This dog-friendly retreat offers the Florida summer your family deserves.

The exterior of the townhome displays beige siding and light brown paneling, complemented by white railings and balconies. Lush green palm trees frame the entrance, and a driveway leads to a private garage. A second floor balcony can be seen with blue chairs.

4.92 out of 5 average rating, 130 reviews

Ruskin Retreat

Our townhome is located in the beautiful Carribean style resort of Little Harbor. Resort amenities for you to enjoy are the large swimming pool and hot tub, basketball court, playground, private kayak launch, private beach (beach chairs and umbrella small fee), water toys for rent. Sunset Bar and Grill adjacent to beach and Hooks by pool , all within walking distance. Disney an hour and a half away and Tampa International Airport only 45 mins.

4.89 out of 5 average rating, 19 reviews

Apartment in Ruskin

The Beach! | Pool, Hot Tub, Gym, Game Room, Tennis

Welcome to the Beach Suite at Little Harbor! This ground-floor, 2-bedroom studio-style suite gives you access to sandy Bahia Beach and the full resort, just a few minutes' walk away. Relax in our sea-inspired condo with: ✨ Bahia Beach 🍸 Cooks Bar & Grill 🏊 Waterfront pool & hot tub 🕹 Game room 🎾 Tennis courts ♨️ Charcoal grills 💪 Fitness center Fully equipped suite for up to 4 guests with kitchenette, bathroom, and smart TV

A pier extends into the water at sunset, surrounded by gentle waves. The sky transitions from orange to purple, reflecting the day's end. Rocks line the shoreline, adding texture to the scene, while lampposts along the pier create a welcoming ambiance.

4.91 out of 5 average rating, 87 reviews

Little Harbor Vacation Retreat

3 bedroom 3 bath townhome nestled in the Little Harbor Resort in Ruskin, Florida. Watch dolphins and manatees swim by from your waterfront balconies. Private parking. Enjoy outdoor pool, hot tub, pickleball, shuffleboard, playground, basketball, and horseshoes on site. Book a sunset cruise, fishing charter, or private excursion from 1 of 2 marinas on site. Eat at Hooks or the Sunset Grill on site.

Popular amenities for Ruskin rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 291 reviews

Home in Largo

TIKI Bar+SAUNA+HOT Tub+Heated POOL! 2 KING beds!

4.93 out of 5 average rating, 27 reviews

A modern kitchen space features dark wood cabinetry and a central island with seating. Stainless steel appliances, including a refrigerator and microwave, are visible, alongside granite countertops. Soft lighting enhances the clean design, creating an inviting area ideal for meal preparation and gatherings.

Home in Wimauma

Home Sun City Center/Wimauma area S of Tampa

4.96 out of 5 average rating, 72 reviews

The family room features a spacious sectional sofa arranged for relaxation. A large flat-screen TV is mounted on the wall, and natural light enters through the nearby windows with blinds. A decorative area rug adds a touch of warmth to the wood-look flooring.

Home in Riverview

Spacious Home w/ heated Pool-SmartTVs-Pool Table

5 out of 5 average rating, 19 reviews

An outdoor kitchen area is showcased under a wooden structure with a peaked roof. Two blue lounge chairs are positioned by a sparkling pool, while a grill, bar stools, and a television are visible in the background, surrounded by lush tropical landscaping.

Home in Ellenton

Trophy Fish at the Oasis

4.97 out of 5 average rating, 108 reviews

A serene pool area is framed by lush greenery, with a clear blue pool inviting relaxation. Gentle steps lead into the water, and a wooden deck extends nearby, offering additional seating. The tranquil view of the lake canal enhances the peaceful atmosphere of the space.

Home in Tampa

Lakeview Retreat with Private Pool Perfect Getaway

5 out of 5 average rating, 12 reviews

A serene outdoor area features a sparkling pool and a raised jacuzzi, both surrounded by a patio with colorful planters. An umbrella casts shade over a seating area, while vibrant yellow and blue accents add a lively touch to the space.

Home in Safety Harbor

Luxe Pool Residence | Downtown | Central Located

4.98 out of 5 average rating, 125 reviews

An aerial view of the tropical backyard reveals a spacious layout with colorful lounge chairs and umbrellas scattered across a gravel surface. Several dining areas, outlined by lush greenery, create inviting spots for relaxation and gatherings, surrounded by the tranquility of the natural setting.

Home in Tarpon Springs

Tropical Pool Retreat in Tarpon Springs

4.92 out of 5 average rating, 36 reviews

Home in Wimauma

South Shore Suites

Condo rentals with a pool

4.9 out of 5 average rating, 112 reviews

A spacious living area features a large sectional sofa with a pullout bed and a circular rug placed beneath a coffee table. Two framed artworks adorn the wall, while light floods in through the window, complementing the warm wood flooring.

Condo in Riverview

Spacious 2/2 ResortStyle Condo near Downtown Tampa

4.83 out of 5 average rating, 100 reviews

An aerial view captures the coastline with soft, sandy beaches meeting vibrant turquoise waters. Nearby, a boat glides through the water, while the shoreline is lined with a mix of buildings and natural landscapes against the backdrop of a colorful sunset.

Condo in Madeira Beach

Lovely-2 bedroom condo with 2 pools, Madeira beach

4.86 out of 5 average rating, 138 reviews

A spacious living area features a comfortable blue sofa, accentuated by decorative cushions. A wooden coffee table centers the room, with two chairs positioned nearby. Large sliding glass doors provide a view of the beach and ocean, creating a bright and airy atmosphere.

Condo in St. Pete Beach

1145 Sqft! - 2 Bedroom 2 Bath (GULF FACING!) Condo

4.97 out of 5 average rating, 209 reviews

A vibrant, themed living area features colorful hanging lamps and intricate wall decorations. Lush greenery is present, alongside a mixture of patterned seating arrangements. Large glass doors open to a balcony, allowing natural light to fill the space and offering a view of the outdoors.

Condo in Tampa

Tiki Themed Waterfront Condo on Tampa Bay

4.89 out of 5 average rating, 208 reviews

A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.

Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

4.91 out of 5 average rating, 144 reviews

A fire table is positioned in view of a vibrant sunset, reflecting shades of orange, pink, and purple across the sky. The scene is framed by large glass panels, offering unobstructed views of the horizon, enhancing the outdoor experience.

Condo in Bradenton

New Luxury 3/3 Condo in Margaritaville Resort

4.99 out of 5 average rating, 212 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.

4.98 out of 5 average rating, 227 reviews

Condo in Longboat Key

Sun-Kissed Memories!

Other holiday rentals with a pool

4.73 out of 5 average rating, 60 reviews

A stilt home features a welcoming wraparound porch, adorned with white railings and seasonal lights. The exterior displays a combination of blue siding and white trim, surrounded by lush greenery. Stairs lead up to the entrance, providing access to the main living area.

Holiday home in Ruskin

Central Florida Vacation Stilt Home with pool!

4.92 out of 5 average rating, 13 reviews

The sandy beach is lined with bright yellow umbrellas providing shade over several lounge chairs. The calm waters of Tampa Bay stretch out beyond, with a pier visible in the distance. A palm tree adds a tropical touch to the serene environment.

Condo in Ruskin

Birdy's on Tampa Bay

A serene marina is captured at sunset, with various boats peacefully anchored in calm waters. Gentle ripples reflect warm hues from the sky, while the distant horizon features soft clouds. Lush greenery is visible in the foreground, framing the tranquil scene.

5 out of 5 average rating, 35 reviews

Beautiful & Spacious 4 bedroom Townhome

4.91 out of 5 average rating, 55 reviews

Home in Palm Harbor

Private Pool! Tropical Beaches! Palm Harbor, FL

5 out of 5 average rating, 11 reviews

Home in Tampa

Allison Palms Luxury Tampa Townhome + Pool

A balcony view showcases a winding waterway bordered by lush greenery and homes along the shore. A small blue table and two chairs are positioned on the balcony, inviting relaxation while enjoying the serene landscape.

4.82 out of 5 average rating, 11 reviews

Townhouse on the Beach in Ruskin

4.88 out of 5 average rating, 17 reviews

A clear swimming pool rests within a screened enclosure, surrounded by tropical greenery. Comfortable lounge chairs are positioned by the water's edge, inviting relaxation. The pool features a connected hot tub, offering options for leisure and enjoyment.

Villa in Wimauma

Coastal Farmhouse & Pool