Holiday rentals with a pool in St. James City

4.93 out of 5 average rating, 99 reviews

Two vibrant blue Adirondack chairs are positioned on a covered porch, inviting relaxation. A welcome sign is displayed nearby, and a potted plant adds a touch of greenery. A decorative rug with a palm leaf design creates a cozy atmosphere on the outdoor space.

Flat in Saint James City

Island Castaway--Free Kayaks

This is the perfect place to sit back, relax and enjoy the view. You have the privacy of a one-bedroom apartment with small kitchen and bath. We are close to great restaurants and some of the best music on the island. Open water and excellent fishing are minutes away. Two kayaks are set up for fishing and are available for guests to use so bring your fishing rod. Pine Island has no beachs, but Ft Myers Beach is about an hour away or take a ferry ride from Bokeelia to Cayo Costa for the day.

A spacious bedroom features a large bed with a textured white coverlet and decorative pillows. Soft lighting is provided by two bedside lamps. A wicker bench sits at the foot of the bed, adorned with rolled towels. Natural light enters through a window framed by sheer curtains.

5 out of 5 average rating, 9 reviews

Quiet Island Get Away - Fishing, Relaxation & Fun

Bring the family! Plenty of space for boat, RV, motorcycle or jetskis! Fully renovated. Small beach around the corner. Fishing, marinas, launching close by. TARPON capital! Aquatic Preserves are excellent for kayaking and canoeing. Community pool $2 for seniors. (Not on property) Take ferry to beautiful beaches of Sanibel, Captiva and Cabbage Key. Quiet - no noise, no crowds and no traffic. "Country living". This is NOT the 24/7 night life of Miami. Thirty minute drive to Ft. Myers.

Superhost

The view features a serene canal surrounded by lush greenery and palm trees. A small boat is visible in the distance, illuminated by a gentle glow from the moonlight reflecting off the water. Soft clouds drift across the twilight sky, adding to the peaceful ambiance.

4.9 out of 5 average rating, 90 reviews

🌴ISLAND TIME! DOCK⚓️POOL🏊🏻‍♀️KAYAKS🛶Boat to Beach🏖 Pets

DIRECT GULF ACCESS HOME - Step back in time, recharge yourself on ISLAND TIME! Pine Island is laid back Old Florida where you can get away from it all. 4 beds, 2 full baths. Steps to dock & canal. Sandy secluded Beaches are minutes away by BOAT! Island Hopping! Don't have a boat, no worries-water taxis & rentals are plentiful on the Island. Golf cart & E-Bikes for rent at the house. Steps to private community pool & jet tub! Manual Bikes & Kayaks included. Sit back & relax! It's time 🐠🏝️

Guest suite in Matlacha Isles-Matlacha Shores

A spacious pool area is viewed with a clear turquoise pool reflecting sunlight. Five lounge chairs are positioned around the pool, with a wooden dock extending towards the water. Lush greenery and potted plants add a natural touch to the surroundings.

4.85 out of 5 average rating, 371 reviews

Moon Shell Hideaway

Private entrance to your one bedroom plus den (with queen size sleeper/sofa) apartment attached to main house. Direct access to the Gulf of Mexico. Bedroom has a queen size bed and the den has a queen size sleeper/sofa. The den doubles as your kitchenette and sitting area with double sliding glass doors that open up to the shared pool and dock area. Gas grill and microwave for cooking (no stove). Boat to five restaurants. Visit the Matlacha Art Galleries. Fish off the dock. WELCOME!

4.94 out of 5 average rating, 108 reviews

The living area features a spacious light-colored sofa accompanied by a rustic coffee table. Large sliding glass doors allow natural light and views of palm trees outside. A flat-screen TV is positioned against a light-coloured cabinet, while a dining table for two is visible on the lanai.

Apartment in Captiva

South Seas Resort Beach Villa 🌴 On The Beach !

South Seas Beach Villa 2527 is located directly on the beach. The beautiful sunsets over the Gulf of Mexico, along with the condo pool can be viewed from the private lanai. This updated unit has one king size bed located in the bedroom and pull out queen size sleeper sofa. The kitchen is fully stocked, there is an inside and outside dining table. You will have access to the beach, pool, pickleball, tennis courts, beach chairs & towels and BBQ grills located in the front of the unit.

Guest suite in Saint James City

A resort-style pool is surrounded by vibrant greenery and tropical landscaping. Lounge chairs and an umbrella provide shaded relaxation areas, while a spacious patio area is paved with light-colored stones. Clear blue skies enhance the inviting outdoor setting.

5 out of 5 average rating, 7 reviews

Studio in Paradise

Welcome to a little slice of paradise… You’re on island time now. Tucked back in a quiet neighborhood, this perfect little getaway provides the ultimate relaxation. Soak up some sun and sip libations while laying out at the resort style pool surrounded by lush vegetation. See the beautiful wildlife that visits the property. Take a short drive to the best tiki bars with nightly live music, or drop the boat at the nearby ramp for some world class fishing and miles of pristine beaches.

The living room features a spacious sectional sofa, providing ample seating. Large glass doors open to the outdoor area, enhancing natural light. A mounted TV displays beach scenery, while a modern fireplace adds a touch of warmth. The room's design promotes comfort and relaxation for guests.

4.98 out of 5 average rating, 121 reviews

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

Superhost

A screened-in pool area features a spacious swimming pool with clear blue water, surrounded by a concrete deck. Lush greenery and palm trees are visible through the screens, creating an atmosphere of tranquility and connection to the outdoors.

4.64 out of 5 average rating, 78 reviews

3/2 Heated Pool, Waterfront w/ Boat Lift!

Fresh and airy pool home on the water in St. James City! This property offers 3 bedrooms, 2 baths and a Florida room that offers ice cold a/c (heat available in the cooler months too) with a queen size swinging bed for extra sleeping! The pool is heated with amazing views overlooking the canal. Bring your boat! Room on the left side of the house for boat trailer parking. This property also includes a boat lift with an extended dock. *Pet friendly, $150 pet fee, 2 pets max.

A refreshing heated saltwater swimming pool is surrounded by a screened enclosure, featuring two sun loungers partially submerged in water. An oversized teal umbrella provides shade, while a small floating tray holds drinks. The serene canal views are visible in the background.

4.97 out of 5 average rating, 149 reviews

Heated Pool & Game Room Waterfront Family Retreat

★ New 4BR/2BA Waterfront Home ★ Top-Rated for Cleanliness & Comfort ★ Heated Saltwater Pool & Hot Tub ★ Screened Lanai + Grill + Sunset Views ★ Fully Stocked Kitchen & Game Room ★ Spacious Open Floor Plan – Sleeps 12 ★ Fishing, Fire Pit & Outdoor Dining ★ Relax Under Palms by the Waterfront ★ Minutes to Cape Coral Beach & Dining ★ Close to Fort Myers, Sanibel & Gulf Fun ✨ Villa Belleriva: Where comfort, style & Florida sunshine meet for an unforgettable stay in paradise.

4.94 out of 5 average rating, 365 reviews

Home in Fort Myers

Whole cozy house

Entire cozy house just for you friends and family. Perfect to spend a pleasant and relaxed moment. If you plan to have a party or event, this place is NOT for you. The neighbors are very strict in terms of noise and large groups of people. Well maintained house. CLEAN POOL BUT NOT HEATED. Walk in to a living area and separated dining. 20 minutes to airport, 25 minutes to the beach, fine dining and entertainment. For a virtual tour, click on the cover photo twice.

A serene waterfront view features private docks with blue canopies, providing shade for two green lounge chairs. A small white boat is visible, securely positioned at the dock. Lush palm trees and a clear blue sky enhance the relaxing outdoor atmosphere.

5 out of 5 average rating, 32 reviews

Tranquility, pool, ocean access, boat lift

Mins to ocean, 2 BR + Den, 3 Baths, private pool, end of Monroe channel, boat lift for up to 21 ft, watch dolphins, fish right off the dock, kayaks, boat ride only mins from Sanibel and Fort Myers Beaches, all the amenities of home + board games, Playstation, 2 adult bikes with helmets. Unwind, enjoy the sunny outdoors with a bar and private pool deck – watch sunsets, sip cocktails, spot dolphins, fish from the docks. Come enjoy waterfront living at its finest!

A screened-in pool area features a sparkling swimming pool surrounded by spacious outdoor deck space. Comfortable seating is visible in the background, along with a large umbrella providing shade. Lush greenery and waterfront views can be seen beyond the pool area, under a bright blue sky.

5 out of 5 average rating, 15 reviews

Blue Agave - 2/2 Pool w/Dockage

Experience laid-back Pine Island vibes at this newly renovated home! Relax with expansive waterfront views, a private pool with screened lanai, and a large dock with boat dockage available. Inside, enjoy a king bed in the master, queen bed in the guest room, and a sleeper sofa. With free laundry and a central location, it’s perfect for exploring local seafood, world-class fishing/boating, and the charm of St. James City. Book now for your tropical retreat!

Popular amenities for St. James City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 19 reviews

Waterview, Heated Pool, Yacht Club

4.95 out of 5 average rating, 118 reviews

An outdoor heated pool is enclosed within a screened patio, featuring a spacious deck with lounge chairs. Lush greenery surrounds the area, and sunlight fills the space, creating an inviting atmosphere for relaxation. The pool's clear water reflects the bright blue sky above.

Home in Fort Myers

McGregor’s Gem• Heated Pool 3BR/2BA River District

A sparkling pool is surrounded by a spacious deck featuring lounge chairs and a shaded seating area with an umbrella. The clear blue sky complements the tranquil setting, while a fence provides privacy for guests enjoying the outdoor space.

4.89 out of 5 average rating, 275 reviews

Modern Oasis pool paradise

An aerial view of a single-story home surrounded by lush green grass and palm trees. The exterior features a warm-colored roof, colorful landscaping, and a pathway leading to the entrance. An American flag is prominently displayed in the front yard.

4.96 out of 5 average rating, 110 reviews

***Relaxation Awaits*** Heated Saltwater Pool Home

A tranquil outdoor space features a heated saltwater pool surrounded by a screened-in lanai. Comfortable seating areas and a dining table are positioned within, enriched by lush greenery visible through the screens.

5 out of 5 average rating, 19 reviews

Pine Island Beach House! *Gulf Access, Heated Poo

4.95 out of 5 average rating, 139 reviews

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

Home in Captiva

Steps to Beach Captiva Includes CLUB & Golfcart

4.91 out of 5 average rating, 169 reviews

Home in Fort Myers

Dive into Luxury: Stunning Tropical Home & Pool

The exterior of a spacious canal-front home is shown, featuring large windows that offer views of the water. A covered docking area is visible, designed for boating, with a solid structure along the waterfront, providing convenient access to the Intracoastal Waterway.

5 out of 5 average rating, 19 reviews

☀️Little paradise☀️

Apartment rentals with a pool

4.83 out of 5 average rating, 117 reviews

The modern kitchen features stainless steel appliances, including a stove and microwave. Adjacent, a stacked washer and dryer are positioned beside a minimalist dining area. Natural light floods the space through a nearby window, highlighting the clean lines and neutral color palette.

Apartment in Fort Myers

Cozy Coastal Escape. Close to FMB and Sanibel

4.89 out of 5 average rating, 254 reviews

A serene view of the Gulf of Mexico features soft waves lapping against a sandy shore, with clear turquoise water meeting an expansive blue sky. The adjacent image shows the condo's exterior with lush green landscaping, highlighting multiple units in a welcoming and well-maintained setting.

Apartment in Sanibel

Rare walkout condo on Sanibel beach

Apartment in Fort Myers Beach

A panoramic view showcases a sparkling heated swimming pool surrounded by lounge chairs, with the beach and Gulf of Mexico visible in the background. Soft waves lap at the shore while sunbathers can be seen enjoying the sandy area. Lush palm trees frame the scene.

4.89 out of 5 average rating, 105 reviews

Beachfront fully equipped apartment

4.97 out of 5 average rating, 30 reviews

A private lanai is visible, featuring a small table with two chairs positioned for ocean views. The scene includes lush greenery, multiple palm trees, and the Gulf of America beyond. The nearby resort buildings add to the tranquil ambiance of the outdoor space.

Apartment in Sanibel

Serene Ocean View Escape at Sundial Resort

5 out of 5 average rating, 10 reviews

A screened lanai features a round glass table surrounded by four wooden chairs with tropical-patterned cushions. Lush palm trees provide a view of the pool area, while bright skies and sunlight enhance the space.

Apartment in Sanibel

Spectacular Sanibel condo near beach with pool

Superhost

A recently renovated open-concept kitchen and living area feature light wood flooring and modern finishes. A large kitchen island with a blue base provides seating and ample workspace. Natural light enters through the sliding glass doors, highlighting a comfortable seating arrangement adjacent to the kitchen.

Apartment in Captiva

4.89 out of 5 average rating, 28 reviews

Waterfront - Bayside Villas Captiva

4.97 out of 5 average rating, 137 reviews

A living area features a black leather sofa, accent chairs, and a flat-screen TV on a light-colored media console. Two framed botanical prints are displayed on a yellow wall, while large sliding glass doors provide sweeping views of the bay and natural light.

Apartment in Fort Myers

2nd Floor Beachfront Condo Sanibel Harbour

5 out of 5 average rating, 44 reviews

A screened lanai features comfortable wicker seating with light blue cushions and a central table, offering an inviting space for relaxation. Large windows showcase breathtaking views of the scenic surroundings, while a ceiling fan adds a cooling touch to the atmosphere.

Apartment in Cape Coral

Stunning Views Penthouse-Waterview King Suite Golf

Other holiday rentals with a pool

4.94 out of 5 average rating, 16 reviews

A scenic balcony view showcases a sunset over the water, framed by wooden railings. Two wooden chairs are positioned on the tiled floor, inviting relaxation while overlooking the vibrant sky filled with oranges and purples, creating a tranquil outdoor setting.

Flat in Fort Myers

Amazing View of Sanibel Harbour

A covered outdoor space features a heated saltwater pool bordered by wide stone tiles. Comfortable lounge seating is seen under an umbrella nearby. Lush greenery and canal views are visible beyond the pool area, offering a serene setting for relaxation.

5 out of 5 average rating, 63 reviews

JAN PROMO: 90° Pool NEW Luxury Spa Gulf Access

4.98 out of 5 average rating, 99 reviews

A dining area features a long wooden table set for eight, surrounded by sleek black chairs. A sideboard holds decorative items, and large windows provide a view of the outdoors, allowing natural light to enhance the minimalist decor.

Villa in Cape Coral

Luxury Canalfront Pool Retreat w/ Upscale Finishes

5 out of 5 average rating, 5 reviews

A modern living space features a comfortable gray sofa adorned with decorative pillows. Large windows offer views of the outdoors, while a dining area, with a table and chairs, is positioned nearby. A sleek kitchen countertop displays tasteful decor, including a vase with white flowers.

Flat in Captiva

Amazing Captiva Bayside Villa

A spacious open-concept living area is showcased, featuring a modern kitchen with an island and sleek cabinetry. Large glass doors provide abundant natural light and views of the outdoors. Rustic wooden beams contrast with the contemporary décor, highlighting both elegance and comfort.

4.91 out of 5 average rating, 68 reviews

AquaLux Smart Home

5 out of 5 average rating, 13 reviews

A screened lanai frames a sparkling pool, reflecting the blue sky and water beyond. Lush greenery lines the pool area, enhancing the view of the calm river. The boat lift is visible, ready for water activities.

Holiday home in Hamlet

Nature Lover's Dream - Waterfront Living Matlacha

5 out of 5 average rating, 18 reviews

Flat in Fort Myers

Luxury II

A modern villa is presented with a sleek facade, featuring a combination of white walls and dark garage doors. Lush green grass and a variety of plants frame the entrance, while a stone pathway leads to the front door under a clear blue sky.