Holiday rentals with a pool in Don Pedro Island

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Top-rated rentals with a pool in Don Pedro Island

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Condo in Englewood
4.79 out of 5 average rating, 141 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

BOOK HERE!!! STEPS TO WORLD FAMOUS Manasota Key BEACH, FREE PARKING. Private beach access. WALKING DISTANCE TO MANY RESTAURANTS. 2 Bedroom, 1 Bathroom, beach themed condo with HEATED POOL access across street. Complimentary grill and Gulf sunsets. Your morning coffee is on us! Beach chairs, towels, and sand toys supplied. Kitchen is updated with filtered water, ice, and utensils supplied. Master Bedroom has a queen sized bed, pull out drawers and fireplace. Boat dock slip available upon request.

Guest favourite
A tranquil pool reflects a colorful sunset with hues of orange and pink in the sky, surrounded by lush greenery. The paved area features decorative stonework, enhancing the serene outdoor setting by the Gulf of Mexico.
Guesthouse in Englewood
4.91 out of 5 average rating, 281 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Top Guest favourite
A contemporary two-story home is depicted overlooking a serene pond. A fountain creates gentle ripples on the water's surface, while palm trees and lush greenery frame the scene, contributing to an inviting outdoor setting.
Home in Placida
5 out of 5 average rating, 18 reviews

Sea La Vie

Escape to 3 acres of tropical bliss on exclusive Palm Island, where luxury meets seclusion. This beautifully updated 5-bedroom, 4-bathroom retreat offers breathtaking views of a serene pond and the Gulf of America. Heated pool & jacuzzi, 50-ft private boat dock, Home theater & game room, Kayaks, bikes, pool table, ping pong, and more, Fire pit, basketball court, volleyball, Steps from a private beach. Accessible only by private ferry, this is more than a getaway; it’s your slice of paradise.

Top Guest favourite
A contemporary dining area features a round table set for four, surrounded by sleek chairs. Large glass walls provide abundant natural light, revealing views of the outdoor space. A modern chandelier hangs above, adding an elegant touch to the inviting atmosphere.
Home in Rotonda West
5 out of 5 average rating, 9 reviews

Turtle Bay - minutes to Boca Grande!

Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!

Top Guest favourite
An aerial view captures a two-story home nestled along a quiet waterway with lush greenery surrounding it. Nearby, other residences and a private dock are visible. The scenic backdrop showcases calm waters merging with a blue sky, highlighting the tranquil atmosphere of the location.
Home in Englewood
5 out of 5 average rating, 39 reviews

Lux Home on Gulf w/Private POOL & 100ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 100 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

Guest favourite
Home in Rotonda West
5 out of 5 average rating, 6 reviews

Huge Pool, Gulf Coast Luxury, Peace & Quiet, Bikes

Our high end ultra modern gulf coast villa is situated on the sunny Cape Haze peninsula in south west Florida. It is a peaceful 4 bedroom retreat with one of the largest private pools in the area, there is a vast south facing lanai /patio overlooking an inland waterway with expansive water views where you can relax in the beautiful Florida sunshine while watching the wonderful local wildlife, there are five bikes, a 75” TV, all within a seamless indoor-outdoor living area.

Top Guest favourite
The exterior of a remodeled home is framed by soft sunset hues, revealing a welcoming entrance with large windows. A landscaped lawn features low-maintenance plants along the pathway leading to the front door, complemented by a spacious driveway and garage.
Home in Rotonda West
4.97 out of 5 average rating, 31 reviews

Luxury Retreat: Oasis with Pool & Putting Green.

This beautiful remodeled home is the perfect getaway for families with children or couples. For the golf enthusiasts, the house includes a putting green and nearby golf courses..It's located minutes from beautiful Englewood beach and several delicious restaurants. You’ll enjoy the heated saltwater pool and gas firepit or have a cookout on the grill while watching a movie on the large outdoor TV. You will always remember your exceptional stay here and want to return.

Guest favourite
A screened lanai displays a spacious pool surrounded by several lounge chairs. Bright sunlight reflects off the water, while palm trees create a serene backdrop. A barbecue grill is positioned nearby, with a clear view of the home and outdoor seating area.
Home in Rotonda West
4.91 out of 5 average rating, 103 reviews

Sun & Sand Spacious Vacation Canal Pool House

Family friendly, fully-renovated PRIVATE 4br/2 bath pool home near Boca Grande & 2 other beaches. 5 golf courses within community. Screened lanai with HUGE 16x25 pool overlooking canal teaming w/ FL wildlife & amazing sunsets. Nature trails nearby for biking, running, walking, & bird watching. Designed for multi-generational use with the master bedroom separate from the 3 guest bedrooms. Fully furnished--just bring your clothes!! Amazing reviews!

Top Guest favourite
A beachfront property is depicted, featuring a two-story structure with a spacious porch. Surrounding landscape includes sand and lush greenery, leading to the waves of the Gulf of Mexico. Sunbathers are seen in the distance, enjoying the beach atmosphere.
Condo in Englewood
4.91 out of 5 average rating, 211 reviews

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

Top Guest favourite
Condo in Englewood
4.97 out of 5 average rating, 105 reviews

Studio, pool, private beach, boat dock shark teeth

Enjoy it all -Pool, private dock & private beach access-located near restaurants. Covered parking or hop on a shuttle to explore Manasota Key! Light, bright condo is complete with everything you will need to relax. Kitchenette has all the must haves-air fryer, portable stove, coffee maker, kettle & community grill. Enjoy a queen bed, shower and community washer/dryer. Fish off the pier, reserve a dock or check out the private beach.

Guest favourite
An aerial view captures the Tropical Island Getaway, showcasing structures with teal roofs nestled among lush greenery. A pool is visible on the left, while the coastline stretches in the background, revealing sandy shores and the serene blue Gulf waters.
Condo in Placida
4.96 out of 5 average rating, 57 reviews

Island Getaway Pool-Ferry-Grocery Delivery Incl.

*FREE Island Grocery delivery/staging Enjoy our Locally Owned and Operated, Newly Updated LGI Condo with Magnificent Views 2 private SW facing decks offer a.m Sun, Gulf, Palm & Pool Views. Beautifully furnished with everything to enjoy your Island time Gated Mainland Parking & Ferry to the Island incl. Walk the Uncrowded shelled beach with Birds, Dolphin and Manatee or Venture out for Prime Fishing & Kayaking SWFlorida has to Offer

Top Guest favourite
A spacious living area is visible, featuring a comfortable armchair and a decorative wooden table. Large glass doors open to a private balcony with ocean views, where tropical plants are visible. Natural light floods the room, highlighting the textured wall art.
Condo in Englewood
5 out of 5 average rating, 10 reviews

Ocean Oasis on Manasota Key - Ocean View

Welcome to our ocean view property, perfect for a relaxing getaway! Enjoy stunning views, walk to restaurants, and indulge in activities like jet skis, kayaking, beach yoga, fishing charters, parasailing, sunset boat trips, and local golf courses. After fun filled day, hang out by the pool with your favorite poolside cocktail! Book now for a serene escape filled with adventure and breathtaking beauty.

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