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AMI_5000R Happy Place

AMI_5000R Happy Place Home of the boathouse bar

AMI_5000R Happy Place

AMI_5000R Happy Place

AMI_5000R Happy Place

AMI_5000R Happy Place

AMI_5000R Happy Place

AMI_5000R Happy Place

12 guests 6 bed 6 bath 4,481 sq ft

Gulf Coast - Anna Maria Island | Holmes Beach

Recommended Rental Flex30

Starting at $499 daily

AMI_222 | Island Life Villa Welcome to Island Life Villa, located on the beautiful Anna Maria Island! This 5-bed, 4-bath villa is 3,338 sq. ft, main house and with attached guest residence, and a pool with the view of the bay.

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

AMI_222 | Island Life Villa

10 guests 5 bed 4 bath 3,338 sq ft

Gulf Coast - Anna Maria Island | Bradenton Beach

Starting at $699 daily

6400 Flotilla Dr, Unit 85

6400 Flotilla Dr, Unit 85

6400 Flotilla Dr, Unit 85

6400 Flotilla Dr, Unit 85

6400 Flotilla Dr, Unit 85

6400 Flotilla Dr, Unit 85

6400 Flotilla Dr, Unit 85

6400 Flotilla Dr, Unit 85

6 guests 2 bed 2 bath

Gulf Coast - Anna Maria Island | Holmes Beach

Starting at $102 daily

AMI_5001R Cozy Cottage

AMI_5001R Cozy Cottage

AMI_5001R Cozy Cottage

AMI_5001R Cozy Cottage

AMI_5001R Cozy Cottage

AMI_5001R Cozy Cottage Take a look at the Waterline on Resort pass

AMI_5001R Cozy Cottage

AMI_5001R Cozy Cottage

2 guests 1 bed 1 bath 400 sq ft

Gulf Coast - Anna Maria Island | Holmes Beach

Recommended Rental Flex30

4.7 (3)

Guest rating

Starting at $95 daily

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

AMI_5002R Happy Place 2

10 guests 5 bed 4 bath 4,000 sq ft

Gulf Coast - Anna Maria Island | Holmes Beach

Recommended Rental Flex30

Starting at $439 daily

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

941 Bunker View Dr

12 guests 5 bed 4 bath 3,676 sq ft

Gulf Coast - Other | Apollo Beach

Starting at $640 daily

26 Heilwood SUNNY ORANGE STAYS presents… ☀️ Forever Sunshine ➠ 26 Heilwood

26 Heilwood Hosting a family reunion, corporate retreat, or destination wedding? This massive 9-bedroom estate is custom-built for large groups, sleeping up to 26 guests.

26 Heilwood Located just a block from the white sands of Clearwater Beach, this home features a private heated pool, an incredible outdoor entertainment bar

26 Heilwood Rooftop terrace with the Gulf views and enough space for everyone to spread out

26 Heilwood Steps to the Sand – A quick 1.5-minute walk puts you directly on the quiet sands of Clearwater Beach.

26 Heilwood The backyard is designed for parties and gatherings.

26 Heilwood Private Heated Pool– Resort-style pool with a waterfall feature, perfect for kids and adults alike (Heat available for a fee)

26 Heilwood Outdoor Tiki Bar – A massive covered entertainment area with a TV and seating—the group's favorite hangout spot.

26 guests 9 bed 5 bath 2,400 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (58)

Guest rating

Starting at $1,189 daily

971 Eldorado SUNNY ORANGE STAYS presents… 🌴 Casa Del Mar ➠ 971 Eldorado

971 Eldorado Private Screened Pool – A sparkling oasis with a waterfall feature, fully screened for comfort (Pool heat available for a fee)

971 Eldorado Comprising a spacious main house and a Casita, this property is the ultimate compound for reunions and large groups.

971 Eldorado Gather the whole extended family at this sprawling 6-bedroom coastal estate, located in the uncrowded North Beach neighborhood of Clearwater.

971 Eldorado Main Living: Comfortable seating and a large Smart TV for movie nights.

971 Eldorado Climate Controlled Florida Room – An extra living space to spread out, play games, or relax out of the sun.

971 Eldorado Steps to North Beach – Located directly across the street from a quiet, residential stretch of sand away from the high-rise crowds.

971 Eldorado Parking for 5 Vehicles – Rare for Clearwater Beach, featuring two separate driveways for hassle-free parking.

12 guests 6 bed 4 bath 2,932 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (21)

Guest rating

Starting at $859 daily

GAR4430 Extra large lanai overlooking the canal. Includes sparkling pool, relaxing hot tub, al fresco dining and more. Pool size: 14' x 28' x 6'

GAR4430 Beautiful 4/3 waterfront home with private pool

GAR4430 Gorgeous, bright, open, fully-equipped kitchen

GAR4430 Double suite attached bathroom with walk-in shower, soaking tub, and double vanities

GAR4430 Beautiful 4/3 waterfront home with private pool

GAR4430 Game room in garage with pool table & foosball

8 guests 4 bed 3 bath 1,940 sq ft

Gulf Coast - Charlotte Harbor | Port Charlotte

Starting at $400 daily

800 Lantana Pool, hot tub, outdoor kichen & TV

800 Lantana Stunning home a short walk to Clearwater Beach

800 Lantana Enjoy the sunset views from your private balcony

800 Lantana Beautiful living room area

800 Lantana Ground floor main kitchen with complete equipment and modern appliances

800 Lantana Pool, hot tub, outdoor kichen & TV

800 Lantana Pool, hot tub, outdoor kichen & TV

800 Lantana Pool, hot tub, outdoor kichen & TV

17 guests 4 bed 5 bath 2,663 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (2)

Guest rating

Starting at $357 daily

20002 Gulf Blvd, PH5 Ocean View

20002 Gulf Blvd, PH5 Incredible Sunsets!!

20002 Gulf Blvd, PH5 Kitchen

20002 Gulf Blvd, PH5 Living Room

20002 Gulf Blvd, PH5 Primary Suite King Bed with sitting chair

20002 Gulf Blvd, PH5 Enclosed Balcony with seating for 4

20002 Gulf Blvd, PH5 Beach and ocean view

20002 Gulf Blvd, PH5 Living Room

12 guests 4 bed 2 bath 2,580 sq ft

Gulf Coast - Indian Rocks Beach | Indian Rocks Beach

4.5 (6)

Guest rating

Starting at $375 daily

HZL17163 Gorgeous 3 bedroom, 2 bathroom waterfront home with private pool

HZL17163 Beautiful, bright, open living space

HZL17163 Bright, open, fully-equipped kitchen

HZL17163 Sparkling pool overlooking canal.

HZL17163 Don't forget your boat! Dock size: 34' x 8'. Dock has electricity and water (No boat lift)

HZL17163 Beautiful primary bedroom with king bed, attached bathroom, lanai access and 75-inch Smart TV

HZL17163 Welcoming foyer

HZL17163 Living room overlooking the sparkling pool and canal beyond. Living room features lots of comfy seating and 75-inch Smart TV

6 guests 3 bed 2 bath 2,100 sq ft

Gulf Coast - Charlotte Harbor | Port Charlotte

Starting at $350 daily

The River View 1008

The River View 1008

The River View 1008

The River View 1008

The River View 1008

The River View 1008

The River View 1008

The River View 1008

8 guests 4 bed 3 bath 2,700 sq ft

Gulf Coast - Cape Coral | Cape Coral

Starting at $338 daily

ANC311 Living Room outdoor view

ANC311 Olympic-size Pool

ANC311 Primary Bedroom/King Bed
50" TV / DVD Player/Balcony access

ANC311 View From Beach

ANC311 Living Room With 75" Smart TV

ANC311 Living Room

ANC311 Living Room

8 guests 3 bed 2 bath 2,400 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $340 daily

ANC611 Pool Table

ANC611 Living Room (Angle)

ANC611 Olympic-size Pool

ANC611 Breakfast Bar

ANC611 Master Bedroom
King Bed
32" Smart TV

ANC611 View From Beach

ANC611 Living Room
50" Smart TV

ANC611 Living Room (Angle 2)

6 guests 3 bed 3 bath 2,400 sq ft

Gulf Coast - Siesta Key | Siesta Key

Starting at $350 daily

GA1978 Our Canal Front House offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

GA1978 A comfortable living room to relax

GA1978 Gorgeous kitchen with plenty of space to prepare any meal

GA1978 Our Canal Front House offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

GA1978 Our Canal Front House offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

GA1978 Our Canal Front House offers a fantastic location to the Harbor and thoughtful touches to make your vacation one to remember!

GA1978 A comfortable living room to relax

GA1978 A comfortable living room to relax

8 guests 3 bed 3 bath 2,913 sq ft

Gulf Coast - Other | Englewood

Starting at $345 daily

22 Laurel SUNNY ORANGE STAYS presents… 🌴 Island Time ➠ 22 Laurel

22 Laurel Indoor/Outdoor Bar – A unique kitchen pass-through window with seating for 10—perfect for serving drinks and snacks poolside.

22 Laurel Resort-Style Pool Area – Private heated pool (fee applies) with a covered cabana and outdoor TV.

22 Laurel Quiet Location – Situated in a quiet residential neighborhood on the north end of Clearwater beach.

22 Laurel Steps to the Beach – Walk to the uncrowded North Beach sands in 1-2 minutes.

22 Laurel Massive Parking – Rare private driveway space for 6–7 vehicles.

22 Laurel Private backyard retreat featuring a sparkling pool, cabana, and plenty of space to unwind.

22 Laurel Resort-Style Pool Area – Private heated pool (fee applies) with a covered cabana and outdoor TV.

16 guests 6 bed 4 bath 1,976 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (26)

Guest rating

Starting at $595 daily

770 Mandalay SUNNY ORANGE STAYS presents… 🌴 Summer Breeze ➠ 770 Mandalay

770 Mandalay 100 Steps to the Beach – Just a 1.5-minute walk to the sugar-white sands of Clearwater Beach.

770 Mandalay Outdoor Tiki Bar – A fun, tropical spot by the pool to serve drinks and hang out.

770 Mandalay Massive Capacity – Sleeps up to 20 guests comfortably with 7 bedrooms and multiple living spaces.

770 Mandalay Single-Level Living – No stairs to navigate, making it perfect for multi-generational families and guests with mobility concerns.

770 Mandalay Cooking for an Army – Equipped with Dual Prep Areas and 3-door full-size fridge to cook for the whole crowd with ease.

770 Mandalay Dining Space for Group Meals

770 Mandalay Comfortable Bedrooms for All

20 guests 7 bed 3 bath 2,500 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (32)

Guest rating

Starting at $727 daily

TED333 Welcome to Champagne Sunset. Relax, unwind, and enjoy

TED333 Gorgeous, open living space overlooking private pool, canal, and nature preserve beyond. Living room features lots of comfy seating and 70-inch Smart TV

TED333 Beautiful, bright, open, fully-equipped kitchen

TED333 Large primary bedroom with king bed, en suite, lanai access, and 55-inch Roku TV

TED333 14' x 6'. Dock with underwater fish lights (Boat lift not available)

TED333 Welcoming foyer

TED333 Welcoming foyer

TED333 Gorgeous, open living space overlooking private pool, canal, and nature preserve beyond. Living room features lots of comfy seating and 70-inch Smart TV

6 guests 3 bed 3 bath 2,570 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $400 daily

MAN8035 Sparkling pool overlooking Lemon Bay

MAN8035 Large, open living space with ample seating, fireplace and 70-inch Smart TV

MAN8035 Large boat dock with power and fish lights (Boat lift is not for guest use.)

MAN8035 Gorgeous, fully-equipped kitchen features high-end stainless-steel appliances, and plenty of storage and counter top space

MAN8035 Stunning 5/4 waterfront home with private pool and beach access on Manasota Key island in Englewood, FL

MAN8035 Lemon Bay & Manasota Key Beach

MAN8035 Large, open living space with ample seating, fireplace and 70-inch Smart TV

MAN8035 Large, open living space with ample seating, fireplace and 70-inch Smart TV

12 guests 4 bed 4 bath 4,560 sq ft

Gulf Coast - Other | Englewood

Starting at $450 daily

806 Lantana Your private backyard oasis features resort-style amenities perfect for relaxing and entertaining.

806 Lantana This spacious coastal home combines luxury, comfort, and resort-style amenities just minutes from the beach.

806 Lantana The fully renovated kitchen offers ample space for preparing meals for large groups.

806 Lantana Designed with comfort in mind, the spacious living room is perfect for movie nights and family time.

806 Lantana Located in a quiet neighborhood just a short walk from the white sands of North Clearwater Beach.

806 Lantana Spend your days lounging poolside and your evenings creating memories with family and friends.

806 Lantana Enjoy easy access to one of Florida's most beautiful beaches while retreating to your private oasis.

806 Lantana Enjoy the perfect blend of privacy and fun in this spacious outdoor retreat.

22 guests 4 bed 4 bath

Gulf Coast - Clearwater Beach | Clearwater Beach

Starting at $100 daily

760 Bay Esplanade Enjoy beautiful Florida sunsets from your private poolside retreat. Take a dip in the pool, unwind in the adjoining spa, or fire up the outdoor grill for a relaxed evening meal.

760 Bay Esplanade Make yourself comfortable in the stunning living room, where soaring vaulted ceilings, cozy seating, a fireplace, and a wall-mounted TV create the perfect setting for relaxing together.

760 Bay Esplanade Relax in a bedroom designed for comfort, with soft carpeting, a spacious bed, and a cozy loveseat at the foot of the bed. Warm wood details and convenient access to the adjoining rooms make this a welcoming retreat.

760 Bay Esplanade Experience the beauty of this coastal neighborhood from above. The property's location offers a wonderful home base for exploring the area's beaches, waterfront scenery, and local attractions.

760 Bay Esplanade Enjoy a little outdoor relaxation on the covered porch, complete with comfortable wicker seating, blue accent pillows, and a cozy conversation table. Palm trees and neighborhood views add to the Florida vacation atmosphere.

760 Bay Esplanade Start your morning with a peaceful moment on the covered balcony. French doors open to this charming outdoor space, where a wicker loveseat invites you to sit back and enjoy the tropical surroundings.

760 Bay Esplanade Take in the beauty of this coastal retreat from above. The elevated view highlights the home's charming balcony, inviting front entrance, spacious paver driveway, and tropical landscaping.

760 Bay Esplanade Wake up to natural light in this charming bedroom. Coastal bedding, comfortable furnishings, and plantation shutters create a peaceful space to recharge between Florida adventures.

10 guests 4 bed 4 bath 3,130 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.5 (4)

Guest rating

Starting at $298 daily

755 Bruce Large private pool

755 Bruce Bedroom 3 - King sized bed

755 Bruce Book Coastal Breeze now and enjoy the comfort, convenience, and coastal vibes of Clearwater Beach – complete with pool, parking, pet‑friendly policy, and everything you need for an unforgettable stay!

755 Bruce Spacious dining area perfect for enjoying meals with the family.

755 Bruce 📍 Perfect Location:

Located just a 4-minute walk to Clearwater Beach, and within 0.6 miles of Beach Walk, Pier 60 Park, and Clearwater Marine Aquarium. Easy access to beach, shopping, dining, and local attractions.

755 Bruce Bedroom 2 - King sized bed

755 Bruce Spacious and cozy living room for a big group + Smart TV

755 Bruce Central air conditioning & heating

8 guests 4 bed 3 bath 1,790 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

4.9 (15)

Guest rating

Starting at $236 daily

930 Mandalay Heated Pool Available – Enjoy year-round swimming (additional fee may apply)

930 Mandalay Bedroom 2 - 1 queen sized bed with ensuite bathroom

930 Mandalay Steps away from the beach!

930 Mandalay Fully Equipped Kitchen – Includes stove, oven, microwave, dishwasher, refrigerator, blender, coffee maker, and toaster

930 Mandalay Enjoy family meals in this Huge dining area that can comfortably sit 6 guests.

930 Mandalay Living room area with bright natural lighting, ceiling fan, smart tv.

Additional Sleeping arrangement: Sofa bed

930 Mandalay Living room area with bright natural lighting, ceiling fan, smart tv.

Additional Sleeping arrangement: Sofa bed

930 Mandalay Living room area with bright natural lighting, ceiling fan, smart tv.

Additional Sleeping arrangement: Sofa bed

6 guests 2 bed 2 bath 1,600 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (3)

Guest rating

Starting at $276 daily

676 Mandalay 111 Sugar Sand Sanctuary condominium features a prime location: Steps away to Clearwater beach!

676 Mandalay 111 Lounge in the spacious living room that features 2 huge couches, a smart tv, and a lot of natural light.

676 Mandalay 111 Bedroom 1 - Queen sized bed

676 Mandalay 111 Sugar Sand Sanctuary condominium features a prime location: Steps away to Clearwater beach!

676 Mandalay 111 Enjoy your meals in this spacious and cozy dining area that comfortably sits 4.

676 Mandalay 111 Lounge in the spacious living room that features 2 huge couches, a smart tv, and a lot of natural light.

676 Mandalay 111 Lounge in the spacious living room that features 2 huge couches, a smart tv, and a lot of natural light.

676 Mandalay 111 Lounge in the spacious living room that features 2 huge couches, a smart tv, and a lot of natural light.

4 guests 2 bed 2 bath 923 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (3)

Guest rating

Starting at $200 daily

1015 Eldorado SUNNY ORANGE STAYS presents… 🌊 Sweet Escape ➠ 1015

1015 Eldorado With floor-to-ceiling windows showcasing Gulf views, a private elevator serving all three floors, and dedicated office space

1015 Eldorado Designed specifically for extended stays, this expansive 4,998 sq. ft. residence offers the ultimate "work from paradise" or winter retreat experience.

1015 Eldorado Stunning Gulf Views – Enjoy daily sunsets from the floor-to-ceiling windows on the 2nd and 3rd floors.

1015 Eldorado Unlike typical week-long rentals, this kitchen is built for daily life.

1015 Eldorado Monthly Executive Rental – Exclusively available for stays of 27+ nights —perfect for snowbirds or corporate relocations.

1015 Eldorado Carlouel Neighborhood: Located in the prestigious North Beach residential enclave, away from the heavy tourist foot traffic.

1015 Eldorado Expansive 5BR/5BA Layout – Nearly 5,000 sq ft of living space allows large groups to spread out comfortably.

12 guests 5 bed 5 bath 4,998 sq ft

Gulf Coast - Clearwater Beach | Clearwater Beach

5.0 (2)

Guest rating

Starting at $382 daily

1612 Lakeview SUNNY ORANGE STAYS presents… 🌴Sandy Retreat Pool House

1612 Lakeview Relax in paradise at this spacious Clearwater home

1612 Lakeview Private Swimming Pool – Make a splash in your own backyard oasis (Note: Pool is not heated or gated).

1612 Lakeview Spacious 3BR/3BA Layout – Rare setup with a dedicated bathrooms for each room ensuring maximum comfort for the whole group.

1612 Lakeview Screened Florida Room – The ultimate hangout spot with comfortable outdoor furniture and a TV to catch the game.

1612 Lakeview Modern Interiors – Recently updated with high vaulted wood-beamed ceilings and a bright, airy feel

1612 Lakeview Relax: Settle into the spacious seating area, bust a movie on a large Smart TV and enjoy the ambiance of the indoor fireplace.

1612 Lakeview Designed for togetherness, the open-concept living area features soaring wood ceilings and abundant natural light.

6 guests 3 bed 3 bath

Gulf Coast - Other | Clearwater

5.0 (4)

Guest rating

Starting at $327 daily

ELD509 Bright, open living space

ELD509 Sparkling private pool faces west

ELD509 En suite with large walk-in shower, double vanities and soaking tub

ELD509 The best of Florida outdoor living. Lanai with outdoor kitchen overlooking the sparkling private pool and canal

ELD509 Bright, open living space. Ample seating and 50-inch Smart TV with HD antenna

ELD509 Bright, open living space

6 guests 3 bed 2 bath 1,976 sq ft

Gulf Coast - Charlotte Harbor | Punta Gorda

Starting at $250 daily

E5S831 Gorgeous, large lanai with sparkling pool overlooking the canal. Lanai also features a dining table for 6 and 32-inch Smart TV. Pool size: 22' x 8' x 6'D

E5S831 Gorgeous Englewood Waterfront Home With Private Pool

E5S831 Guest bedroom 4 features 2 twin over twon bunkbeds and 43-inch Smart TV

E5S831 Complimentary kayaks (Boat lift not available)

E5S831 Gorgeous Englewood Waterfront Home With Private Pool (Boat lift not available)

E5S831 Beautiful, fully-equipped kitchen

E5S831 BBQ grill in backyard with path leading to boat dock and canal (Boat lift not available)

E5S831 Large living room overlooking pool. Living room features comfy, ample seating and large 65-inch Smart TV

12 guests 5 bed 3 bath 2,344 sq ft

Gulf Coast - Other | Englewood

Starting at $400 daily

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

1465 Satsuma St

10 guests 4 bed 2 bath 1,958 sq ft

Gulf Coast - Other | Clearwater

4.9 (8)

Guest rating

Starting at $249 daily

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7533 Osceola Polk Line Rd, Davenport, Fl 33896

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